instruction stringlengths 151 5.17k | output stringlengths 291 4.64k |
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Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of bis-(4-chloro-phenyl)-acetic acid methyl ester (1.19 g, 4.0 mmol) in THF (20 ml) was cooled to −78° C. under nitrogen. A solution of LDA (3.0 mL, 6.0 mmol, 2M in heptane/THF/ethylbenzene) was ... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "bis-(4-chloro-phenyl)-acetic acid methyl ester"}], "amount": {"mass": {"value": 1.19, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 20.0, "units": "MILLI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a cold solution of cis-N-Boc-4-hydroxy-L-proline (10 g. 1 eq.), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU 15.5 g, 1.12 eq.) and N-methylhex-5-en-1-amine tosylate salt 32a... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "DIPEA"}], "amount": {"volume": {"value": 29.4, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "cis-N-Boc-4-hydroxy-L-proline"}], "amount": {"mass": {"value": 10.... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 1-(3-(4-chlorophenyl)isoxazol-5-yl)ethanamine (610 mg, 2.74 mmol) and (R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-fluoropyrimidin-4-yl)oxazolidin-2-one (774 mg, 2.74 mmol) in DMSO (5 ml) was adde... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(3-(4-chlorophenyl)isoxazol-5-yl)ethanamine"}], "amount": {"mass": {"value": 610.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(R)-4-((R)-1-(tert-butoxy)ethyl)-3-(2-fluoropyrim... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1-(6-Chloromethylpyridin-2-ylmethyl)-5-(1,3-dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (1.0 g, 2.8 mmol) was added to piperidine (2 ml), followed by stirring in an argon atmosphere at 100° C. for 2 hours.... | {"inputs": {"m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m1_m2": {"co... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1.41 g (10.2 mmol) of 4-hydroxybenzoic acid and 3 g (10.2 mmol) of (1.1) were suspended in 25 ml of DMF. 1.38 g (10.2 mmol) of 1-hydroxy-benzotriazole (HOBt) and, at 0° C., dicyclohexylcarbodiimide (DCCI) w... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-hydroxybenzoic acid"}], "amount": {"mass": {"value": 1.41, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "( 1.1 )"}], "amount": {"mass": {"value": 3.0, "units": "GRAM"}},... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was synthesized from ethyl 5-methyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate (0.017 g, 0.09 mmol) and lithium hydroxide monohydrate (0.019 g, 0.45 mmol) according to General P... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 5-methyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate"}], "amount": {"mass": {"value": 0.017, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "lithium hydroxide monohydrate"}], "amo... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of N-(2-aminoethyl)-4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxamide (2.50 g, 5.90 mmol) in toluene (20 mL) was added phosphoryl chloride (4.70 mL, 50.0 mmol) and the m... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(2-aminoethyl)-4-cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxamide"}], "amount": {"mass": {"value": 2.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared in a similar manner as described for example 8 from 6-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-methyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide (90 mg, 0.... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "6-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-methyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide"}], "amount": {"mass": {"value": 90.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
EtOH (15 mL) and 150 μL of H2SO4 (conc.) were added into the compound 10c (5.03 mmol) and the mixture was heated to 80° C. for 45 minutes with stirring. The solvent was partially evaporated to half of the o... | {"inputs": {"m3_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "H2SO4"}], "amount": {"volume": {"value": 150.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "compound 10c"}], "amount": {"moles": {"value": 5.03, "units": "MILLIMOLE"}}, "reaction_ro... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution comprising 2.4 grams of potassium hydroxide, 201 grams 4-acetoxystyrene and 500 grams of methanol was heated at reflux for 2.2 hours. The reaction was cooled to 12° C. and 64 grams potassium hydr... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium hydroxide"}], "amount": {"mass": {"value": 2.4, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-acetoxystyrene"}], "amount": {"mass": {"value": 201.0, "units": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
This compound was prepared from N-(4-bromophenyl)-N-(5-methyl-1,3-benzoxazol-2-yl)amine (0.50 g, 1.65 mmol), methyl (1R,2R)-2-(4-bromobenzoyl) cyclopentanecarboxylate (0.57 g, 1.83 mmol, 94.5% ee) in a simi... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(4-bromophenyl)-N-(5-methyl-1,3-benzoxazol-2-yl)amine"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl (1R,2R)-2-(4-bromobenzoyl) cyclopentanecarbox... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 10 g 4-{4-[5-(4-methanesulfonyl-phenyl)-4-methyl-2-oxo-oxazolidin-3-yl]-butyl}-5-oxo-[1,4]diazepane-1-carboxylic acid tert-butyl ester, 1 g of 20% palladium hydroxide on carbon, 10 ml water, an... | {"inputs": {"m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium formate"}], "amount": {"mass": {"value": 3.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "S... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 0.09 g of sodium hydride (60% oil dispersion) in 10 ml of N,N-dimethylformamide, there was added dropwise a solution of 0.45 g of 2-chloro-4-phenoxyphenol in 3 ml of N,N-dimethylformamide w... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydride"}], "amount": {"mass": {"value": 0.09, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 1-(4-chlorophenyl)ethanone (2.0 g, 12.9 mmol) in anhydrous THF was cooled in a dry ice acetone bath and treated with sodium hexamethyldisilazid (14.2 mL, 1M in THF, 14.2 mmol). The resulting s... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "tetrahydro-pyran-4-carbonyl chloride"}], "amount": {"mass": {"value": 1.92, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "reaction_role": "SOLVENT"}]}, "m1_m4": {"components": [{"iden... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Reaction and post treatment were carried out in the same manner as in Example 4-(b) except for using 0.70 g (1.01 mmol) of 2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-(1-ethylpropoxymethyl)-1,5-bis(2-trime... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(3-cyclopropoxy-4-difluoromethoxyphenyl)-3-(1-ethylpropoxymethyl)-1,5-bis(2-trimethylsilylethoxymethyl)-1,5-dihydropyrrolo[2,3-d]pyridazin-4-one"}], "amount": {"mass": {"value": 0.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Under an argon atmosphere, 2.0 M aqueous Na2CO3 (0.66 mL) was added to a mixture of Intermediate 147(d) of Example 147 (100 mg, 0.265 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-p... | {"inputs": {"m1_m2_m3_m5_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Na2CO3"}], "amount": {"volume": {"value": 0.66, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Intermediate 147(d)"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}},... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 53.7 g of (3-chlorophenyl)hydrazine hydrochloride, 50.8 g of ethyl(ethoxymethylene)cyanoacetate and 41.4 g of potassium carbonate in 500 ml of ethanol was refluxed for 20 hours. The solution w... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "(3-chlorophenyl)hydrazine hydrochloride"}], "amount": {"mass": {"value": 53.7, "units": "GRAM"}}, "reaction_role": "REACT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 2.5 g (0.015 mole) of 1-heptyl-1H-imidazole and 3.66 g (0.015 mole) of 1-(4-bromobutyl)-4-methoxybenzene is heated at 140° C. for about 2 hours. Follow the progress of the reaction by thin-laye... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-heptyl-1H-imidazole"}], "amount": {"mass": {"value": 2.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-(4-bromobutyl)-4-methoxybenzene"}], "amount": {"mass": {"value": 3.66, "units": "GRA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-Chloromethyl-6-isopropylsulfanyl-pyridine (40 mg, 0.19 mmol) obtained in Step C of Preparation Example 16 and 2-(3-chloro-4-hydroxy-phenyl)-cyclopropane carboxylic acid ethyl ester (52 mg, 0.21 mmol) obta... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-Chloromethyl-6-isopropylsulfanyl-pyridine"}], "amount": {"mass": {"value": 40.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-(3-chloro-4-hydroxy-phenyl)-cyclopropane carboxylic acid... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of N-[1-(3′-amino-4-biphenylyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-N-methylacetamide (70.8 mg, 0.12 mmol) in dichloromethane (1 mL) was added pro... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "resultant mixture"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-[1-(3\u2032-amino-4-biphenylyl)-2-(4-morpholinyl)ethyl]-2-(6,7-dichloro-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)-... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
An analysis of the crude reaction solution by gas chromatography revealed that the conversion of 1,1,1-trichloro-2-methyl-2-propanol was 67.7% and the yield of methyl 2-chloro-2-methylpropanoate was 36.5%. ... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1,1,1-trichloro-2-methyl-2-propanol"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 2-chloro-2-methylpropanoate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_d... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 158 mg (0.5 mmol) of (3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid (Intermediate 1), 96 mg (0.5 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (... | {"inputs": {"m1_m2_m3_m4_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "(3R)-3-[(tert-butoxycarbonyl)amino]-4-(2,5-difluorophenyl)butanoic acid"}], "amount": {"mass": {"value": 158.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Intermediate 1"}], "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred refluxing solution of N1-(4-chlorophenyl)benzene-1,2-diamine (200 mg, 0.92 mmol) in toluene (20 mL) was added drop-wise a solution of 2,2-dimethylmalonyl dichloride (155 mg, 0.92 mmol). Then th... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N1-(4-chlorophenyl)benzene-1,2-diamine"}], "amount": {"mass": {"value": 200.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "toluene"}], "amount": {"volume": {"value": 20.0, "units": "MIL... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of (3S,4R)-3-[(R)-1-Phenyl-ethylamino]-tetrahydro-pyran-4-carboxylic acid ethyl ester (726 mg, 2.6 mmol) in tetrahydrofuran (6 mL) was treated with 1.0 M sodium hydroxide solution (5.2 mL, 5.2 mm... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(3S,4R)-3-[(R)-1-Phenyl-ethylamino]-tetrahydro-pyran-4-carboxylic acid ethyl ester"}], "amount": {"mass": {"value": 726.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydroxid... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
10 cm3 of thionyl chloride are added at 22° C. under an argon atmosphere to 1 g (2.3 mmol) of 3-carboxy-1-(quinol-3-yl)-1H-indole. After stirring at reflux for 1.5 hours, the reaction mixture is concentrate... | {"inputs": {"m2_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-carboxy-1-(quinol-3-yl)-1H-indole"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "thionyl chloride"}], "amount": {"volume": {"value": 10.0, "units": "MILL... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The reaction and aftertreatment were conducted in the same manner as in Example 155i by using the 5-chloro-4-{[(1S*,2R*)-5,5-difluoro-2-{1-[(2-methoxyethoxy)methyl]-1H-pyrazol-5-yl}cyclohexyl]oxy}-N-(2,4-di... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 3.0, "unit... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of sodium hydride (0.54 g, 95%, 20 mmol) in DMF (25 mL) was added [1,2]thiazinane 1,1-dioxide (2.70 g, 20 mmol). After stirring the mixture at room temperature for 15 min, 2-fluorobenzonitri... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydride"}], "amount": {"mass": {"value": 0.54, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "SOLV... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
One droplet of DMF was added to a solution of 1-[(1-ethylpyrazol-4-yl)methyl]-7-(4-propoxyphenyl)-2,3-dihydro-1-benzazepine-4-carboxylic acid (330 mg) in dichloromethane (15 ml). Then, thionyl chloride (118... | {"inputs": {"m3": {"components": [{"identifiers": [{"type": "NAME", "value": "thionyl chloride"}], "amount": {"mass": {"value": 118.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "DMF"}], "reaction_role": "REACTANT"}, {"identifiers": [{"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 3-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one (6.82 g, 19.0 mmol) in 100 mL of isopropanol was added a solution of potassium cyanide (2.48 g, 38.1 mmol) in 10 mL of water... | {"inputs": {"m1_m4_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(bromomethyl)-6-methoxy-2-methyl-4-phenylisoquinolin-1(2H)-one"}], "amount": {"mass": {"value": 6.82, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium cyanide"}], "amount": {"ma... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Methanesulphonyl chloride (1.82 ml, 23.5 mmol) was added dropwise over 10 minutes to an ice-cold solution of tetrahydro-2H-pyran-4-ol (2.0 g, 19.6 mmol) and triethylamine (3.56 ml, 25.5 mmol) in dichloromet... | {"inputs": {"m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Methanesulphonyl chloride"}], "amount": {"volume": {"value": 1.82, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ice"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In the same manner as in Reference Example 13, N-(4-iodophenyl)pyrimidin-2-amine (300 mg) and propyl bromide (0.11 ml) were reacted in the presence of sodium hydride to obtain N-(4-iodophenyl)-N-propylpyrim... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(4-iodophenyl)pyrimidin-2-amine"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "propyl bromide"}], "amount": {"volume": {"value": 0.11, "units":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
11.9 g of 3,4,5-trimethoxyaniline, 11.6 g of bis-(2-chloroethyl)amine hydrochloride, 9 g of anhydrous potassium carbonate, and 48 ml of diglyme were mixed and refluxed under heating for 28 hours. The reacti... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium hydroxide"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "3,4,5-trimethoxyaniline"}], "amount": {"mass": {"value": 11.9, "units": "GRAM"}}, "reaction_role": "REACTANT"},... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirring solution of [3-(4-pyrrolidin-1-ylmethyl-phenyl)-cyclobutyl]-methanol (50.0 mg, 0.20 mmol) prepared above (Step F) in 3 mL of tetrahydrofuran was added a solution of KotBu (0.42 mL, 0.41 mmol, ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 1.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "[3-(4-pyrrolidin-1-ylmethyl-phenyl)-cyclobutyl]-methanol"}], "amount": {"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 1-cyclopentyl-3-ethyl-6-oxo-5-phenyl-4,6-dihydro-1H-pyrazolo[3,4-c]pyrrole (0.17 g, 0.58 mmole) in anhydrous ether (15 ml) was added lithium aluminum hydride (0.17 g, 4.6 mmole). Th... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-cyclopentyl-3-ethyl-6-oxo-5-phenyl-4,6-dihydro-1H-pyrazolo[3,4-c]pyrrole"}], "amount": {"mass": {"value": 0.17, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "lithium aluminum hydride"}], ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of crude (±) (6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid (11.9 g, 84.9 mmol, assume 100% potency) in 119 mL of 6:1 ethyl acetate:ethanol at reflux is added 18 g (85.1 mmol) of (S)-N-benzy... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(\u00b1) (6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid"}], "amount": {"mass": {"value": 11.9, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "REACTANT"}, {"id... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Dissolve (R)-1-(5-bromo-pyridin-2-yl)-pyrrolidin-3-ylamine (1.60 g, 6.63 mmol) in CH3OH (915 mL). Add (1-ethoxy-cyclopropoxy)-trimethyl-silane (2.7 mL, 13.49 mmol) and HOAc (1.9 mL, 33.15 mmol) and stir at ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "NaBH3CN"}], "amount": {"mass": {"value": 4.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(1-ethoxy-cyclopropoxy)-trimethyl-silane"}], "amount": {"volume": {"value": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3-Hydroxy-2-methyl-4-quinoline carboxylic acid (549 mg), 6-benzyloxy-4-chloro-7-methoxyquinoline (810 mg), and 4-(N,N-dimethylamino)-pyridine (990 mg) were dissolved in 1,2-dichlorobenzene (40 ml) to prepar... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-Hydroxy-2-methyl-4-quinoline carboxylic acid"}], "amount": {"mass": {"value": 549.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "6-benzyloxy-4-chloro-7-methoxyquinoline"}], "amo... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a one liter reaction flask were dissolved 220.0 g of resorcinol in 300 ml of de-mineralized water. To this solution 18.22 g of 2,6-bis(hydroxymethyl)-3,4-dimethylphenol was added and stirred until it dis... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 300.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Firstly, 24.3 g (100 mmol) of N-phenylcarbazole was dissolved in 600 ml of glacial acetic acid, and 17.8 g (100 mmol) of N-bromo succinic acid imide was slowly added thereto. The mixture was stirred for ove... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N-phenylcarbazole"}], "amount": {"mass": {"value": 24.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 600.0, "units": "MILLILITER"}}, "reaction_... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Using similar reaction conditions as described in step-i of example-1,5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine (Intermediate 1) (300 mg, 0.709 mmol) was coupled with 1-(3-fluorobenzyl)-3-methyl-4-(4... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1,5-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridine"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium carbonate"}], "amount"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 4-(dimethoxymethyl)benzaldehyde (25.0 g, 120 mmol), pyrrolidine (10.0 ml, 120 mmol), acetic acid (6.87 ml, 120 mmol) and anhydrous sodium sulfate (34.1 g, 240 mmol) in dichloromethane (300 ... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "Potassium carbonate"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m4_m7_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(dimethoxymethyl)benzaldehyde"}], "amount": {"mass": {"value": 25.0, "units": "GRAM"}}, "reaction_role"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
cis-3,3-Dibromo-2-oxobicyclo[4.2.0]-octane-1-acetic acid ethyl ester (14.16 g) lithium bromide (4.88 g, 56.21 mmol), and lithium carbonate (2.98 g, 14.4 mmol) were dissolved in 47.3 mL of DMF under nitrogen... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "cis-3,3-Dibromo-2-oxobicyclo[4.2.0]-octane-1-acetic acid ethyl ester"}], "amount": {"mass": {"value": 14.16, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "lithium carbonate"}], "amount": {"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a cooled solution of sodium ethoxide (from 2.3 g. sodium and absolute ethanol, 30 ml.) was added with shaking ethyl acetoacetate (13 g.). When homogeneous the mixture was treated with ethyl cinnamate (17... | {"inputs": {"m3_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetoacetate"}], "amount": {"mass": {"value": 13.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium ethoxide"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "react... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a mixture of 5.0 g (21.9 mmol) of 4-benzyloxy-benzoic acid in 25 mL of dichloromethane (DCM) was added dropwise 10 mL (114 mmol) of oxalyl chloride, followed by 5 □L of dimethylformamide (DMF cat) and th... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-benzyloxy-benzoic acid"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 2-(tert-butoxycarbonylamino)-cyclopentanecarboxylic acid (6-chloro-9H-β-carbolin-8-yl) amide (736 mg, 1.72 mmol) in trifluoroacetic acid (5 ml) was stirred at RT for 20 min, then concentrated ... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(tert-butoxycarbonylamino)-cyclopentanecarboxylic acid (6-chloro-9H-\u03b2-carbolin-8-yl) amide"}], "amount": {"mass": {"value": 736.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tri... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Preparation of tert-Butyl 4-(3-tert-butylphenylcarbamoyl)-4-methylpiperidine-1-carboxylate. To a solution of 1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (0.30 g, 1.2 mmol), DMF (20 drops), ... | {"inputs": {"m2_m6_m3_m7_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid"}], "amount": {"mass": {"value": 0.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyridine"}], "amount": {"mass": {"valu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a cold (0° C.) solution of 2-chloro-6-hydroxymethyl-nicotinic acid methyl ester (4.98 g, 24.8 mmol) in dichloromethane (161 mL) was added mesyl chloride (2.5 mL, 29.8 mmol). The reaction mixture was allo... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-6-hydroxymethyl-nicotinic acid methyl ester"}], "amount": {"mass": {"value": 4.98, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "mesyl chloride"}], "amount": {"volume": {"value": 2... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1.53 g (5 mmol) of 3-[4-(imidazo[1,2-a]pyridin-5-ylthio)butyl]oxazolidine-2,4-dione and 20 ml of ethanol were placed in a reaction flask, followed by stirring at 60° C. for 20 minutes, to dissolve the start... | {"inputs": {"m6_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-phenylpropionaldehyde"}], "amount": {"volume": {"value": 0.66, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "SOLVENT"}]}, "m7_m2": {"components": [{"ident... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of alcohol 3 (342 mg, 1.0 mmol) in CH2Cl2 (3 mL) was treated with (2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-piperidinecarboxylic acid (23, 255 mg, 1.0 mmol, prepared from L-pipecolic acid in 4 step... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "alcohol"}], "amount": {"mass": {"value": 342.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-piperidinecarboxylic acid"}], "amount": {"mass": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
At room temperature, a solution of 0.63 ml (5 mmol) of 4-chloro-benzo)yl chloride in 5 ml of absolute tetrahydrofuran is added dropwise with stirring to a mixture of 1.72 g (5 mmol) of 2-(1-chloro-cycloprop... | {"inputs": {"m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(1-chloro-cyclopropyl)-1-(2-chlorophenyl)-3-(5-mercapto-1,2,4-triazol-1-yl)-propan-2-ol"}], "amount": {"mass": {"value": 1.72, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carb... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
10.0 g (37.7 mmol) of methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate were introduced into 50 ml of toluene, together with 10.17 g (75.4 mmol) of N-cyano-N-methylmethanesulphonamide ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "titanium tetrachloride"}], "amount": {"mass": {"value": 3.61, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 4-iodophenyl acetate (7.86 g, 0.030 mole) and 1,14-diiodoerfluoro-5,10-dimethyl-3,6,9,12-tetraoxatetradecane (9.20 g, 0.010 mole) in 45 ml of N,N-dimethylformamide was added copper bronze (... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "val... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a mixture of ethyl 2-(2-acetamidopyridin-4-yl)-4-bromothiazole-5-carboxylate (190 mg, 0.510 mmol) and bis(tri-t-butylphosphine)palladium(0) (65.6 mg, 0.128 mmol) under nitrogen was added a 0.500 M soluti... | {"inputs": {"m1_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 2-(2-acetamidopyridin-4-yl)-4-bromothiazole-5-carboxylate"}], "amount": {"mass": {"value": 190.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "bis(tri-t-butylphosphine)palladium(0)... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 5-bromo-8-(tert-butyldimethylsilanyloxy)-2-trifluoromethylquinoline (21 g) in methanol (150 ml) was treated with 37% hydrochloric acid solution (5 ml) and water (5 ml) The mixture was stirred ... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "5-bromo-8-(tert-butyldimethylsilanyloxy)-2-trifluoromethylquinoline"}], "amount": {"mass": {"value": 21.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of p-aminobenzoylacetonitrile, 1-bromohexadecane, potassium carbonate and hexamethylphosphoramide is heated to 80° C. for 20 hours and worked up as in Example 1, providing 4-hexadecylaminobenzoyla... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "p-aminobenzoylacetonitrile"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-bromohexadecane"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "reactio... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Trimethylaluminium (2M in toluene) (0.638 mL, 1.28 mmol) was added to 6-aminonicotinonitrile (152 mg, 1.28 mmol) in toluene (2 mL) under nitrogen. The resulting solution was stirred at room temperature for ... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "(2S)-methyl 3-(2-(tert-butyldiphenylsilyloxy)ethoxy)-2-(1-(2,3-dichlorophenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy)propanoate"}], "amount": {"mass": {"value": 425.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
With a procedure similar to example 50 above, 4-(2-methylsulfanyl-ethyl)-2-phenyl-oxazole-5-carboxylic acid (6-morpholin-4-yl-pyridin-3-yl)-amide was prepared from 4-(2-methylsulfanyl-ethyl)-2-phenyl-oxazol... | {"inputs": {"m0_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(2-methylsulfanyl-ethyl)-2-phenyl-oxazole-5-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "6-morpholin-4-yl-pyridin-3-ylamine"}], "reaction_role": "REACTAN... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Following General Procedure B, 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (100 mg, 0.32 mmol) was reacted with 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole (120 mg, 0.48 mmol) to afford... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "6-(4,4,5,5-tetramethyl-1,3,2-di... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred mixture of (R)-4-(benzenesulfonyl)-3-(Prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-one (2.7 g, 9.77 mmol) and Et3SiH (16 mL, 97.7 mmol) in CH2Cl2 (30 mL) was added TFA (16.7 g, 147 mmol). The reaction... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-4-(benzenesulfonyl)-3-(Prop-2-ynyl)-3,4-dihydropyrazin-2(1H)-one"}], "amount": {"mass": {"value": 2.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Et3SiH"}], "amount": {"volume": {"va... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 2-(2-chloro-phenyl)-5-isopropyl-3-vinyl-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one 1A-8 (42 mg), palladium acetate (3 mg) and 4-chloroiodobenzene (300 mg) were stirred for 18 hours.... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(2-chloro-phenyl)-5-isopropyl-3-vinyl-4,5-dihydro-2H-pyrrolo[3,4-c]pyrazol-6-one"}], "reaction_role": "REACTANT"}]}, "m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloroiodobenzene"}], "amount": {"mass": {"value": 3... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In 250 ml of water-dioxane (1:1) was suspended 10 g of 2-(2,5-dioxopyrrolidin-3-yl)glycine and under cooling at 0°-5° C. the above amino acid was dissolved by addition of 70 ml of 1 N sodium hydroxide. To t... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "benzyloxycarbonyl chloride"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water dioxane"}], "amount": {"volume": {"value": 25... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 3-[1-(4-pyridyl)piperazinyl]-1,2-benzisoxazol-6-ol (0.80 g) in pyridine (10 ml) was added dimethylcarbamyl chloride (0.70 g) under N2. The reaction was heated to 85° C. for 2 hours.... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-[1-(4-pyridyl)piperazinyl]-1,2-benzisoxazol-6-ol"}], "amount": {"mass": {"value": 0.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dimethylcarbamyl chloride"}], "amount": {"mass": {"val... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 4-fluoro-2-(2-fluoro-6-methoxyphenoxy)-1-nitrobenzene (1.33 g, 5 mmol) and sodium methoxide (035 g, 6 mmol) in DMF (10 ml) was heated at 80° C. for 2 h. The mixture was poured into water and wa... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-fluoro-2-(2-fluoro-6-methoxyphenoxy)-1-nitrobenzene"}], "amount": {"mass": {"value": 1.33, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium methoxide"}], "amount": {"moles": {"value":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared according to the procedure described in Example 139, Step 1, using 2,6-dibromo-pyridine and oxazolidin-2-one.
### ORD JSON:
| {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2,6-dibromo-pyridine"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "oxazolidin-2-one"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "workups": [{"typ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Tin(II) chloride dihydrate (346.3 g, 1.54 mol) was added to a solution of 2,3,6,7-tetrachloro-5-nitroquinoxaline (96.2 g, 0.31 mol) in ethyl acetate (1.8 L). The mixture was heated under reflux for 4 hours,... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Tin(II) chloride dihydrate"}], "amount": {"mass": {"value": 346.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2,3,6,7-tetrachloro-5-nitroquinoxaline"}], "amount": {"mass": {"value": 96.2... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirring solution of 8-fluoro-3,4-dihydroquinolin-2(1H)-one (1.6 g, 9.69 mmol) and acetyl chloride (1.722 mL, 24.22 mmol) in carbon disulfide (20 mL, 9.69 mmol) at 0° C. was added in portions aluminum ... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "8-fluoro-3,4-dihydroquinolin-2(1H)-one"}], "amount": {"mass": {"value": 1.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetyl chloride"}], "amount": {"volume": {"value": 1.722, "unit... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared according to the described general procedure 1 (GP1) by reaction of methyl 6-amino-6-(2,6-dimethoxyphenyl)hexanoate with commercially available 3-(2-methylthiazol-4-yl)benzaldehyde. Subsequent puri... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 6-amino-6-(2,6-dimethoxyphenyl)hexanoate"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-(2-methylthiazol-4-yl)benzaldehyde"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
First, 134 g of 2-nitrophenanthrene, 1.00 g of palladium carbon, and 1.2 L of ethanol were loaded, and then 70 mL of hydrazine monohydrate were added to the mixture. The reaction solution was stirred for 4 ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "palladium carbon"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-nitrophenanthrene"}], "amount": {"mass": {"value": 134.0, "units": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2.0 g of 2-(4,6-dimethoxypyrimidin-2-yl)-3-methyl-N-methylsulfonylbutyric acid amide was placed in a round bottomed flask, and was dissolved in 50 ml of DMF. To the resultant solution, was gradually added 0... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydride"}], "amount": {"mass": {"value": 0.28, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m8": {"components": [{"i... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of ethyl 1-benzyl-2-hydroxymethylimidazole-4-carboxylate (described immediately above, 1 g), an aqueous ammonium hydroxide solution (specific gravity 0.88 g/ml, 60 ml) and ethanol (25 ml) was stir... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 1-benzyl-2-hydroxymethylimidazole-4-carboxylate"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium hydroxide"}], "amount": {"volume": {"value": 60.0, "units": "MILLILITER"}}, "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In 3 liters of dry ethanol, 75 g of 4,4'-bismethoxybenzoin and 21 g of sodium borohydride were refluxed for 2 hours. After adding 250 ml of concentrated hydrochloric acid to the reaction mixture, the result... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "amount": {"volume": {"value": 1300.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4,4'-bismethoxybenzoin"}], "amount": {"mass": {"value": 75.0... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The procedure used for the preparation of 3a was repeated with 2,6-dihydroxybenzonitrile (8.75 g, 64.8 mmol), (EtO)2P(S)SH (32.6 mL, 194 mmol) and water (26 mL) at 60° C. for 36 hr to give 3b (4.76 g, 43%) ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3a"}], "reaction_role": "REACTANT"}]}, "m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2,6-dihydroxybenzonitrile"}], "amount": {"mass": {"value": 8.75, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 2-methyl-N-{3-[5-(3-methyl-5-{([4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]oxetan-3-yl}propane-2-sulfinamide (Example 59, Step 2, 75 mg, 0.147 mmol) in dichloromethane (1... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "reaction_role": "SOLVENT"}]}, "m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-methyl"}], "amount": {"mass": {"value": 75.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
15.0 g 2-chloro-N-(2,2-dimethoxy-ethyl)-N-methyl-acetamide in 80 ml acetonitrile are added dropwise within one hour to a suspension of 10.6 g (trans)-4-aminocyclohexanol, 16.25 g sodium carbonate and 0.64 g... | {"inputs": {"m1_m5_m2_m3_m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-N-(2,2-dimethoxy-ethyl)-N-methyl-acetamide"}], "amount": {"mass": {"value": 15.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(trans)-4-aminocyclohexanol"}], "amount": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared from 5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid and 4-amino-3-chloropyridine by the method described in Example 2 Method B reversing the order of addition such that so... | {"inputs": {"m3": {"components": [{"identifiers": [{"type": "NAME", "value": "acid chloride"}], "reaction_role": "REACTANT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carboxylic acid"}], "reaction_role": "REACTANT"}, {"identifiers": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
12-Chloro-dodec-5-yne (1 mmol) was mixed with potassium iodide (3 mmol) and 3-picoline (3 mmol) in butanone. The mixture was refluxed for 3 days and cooled to room temperature, filtrated. The butanone was r... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "12-Chloro-dodec-5-yne"}], "amount": {"moles": {"value": 1.0, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium iodide"}], "amount": {"moles": {"value": 3.0, "units": "MILLIMOL... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
(2-Methyl-1-{2-[4′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-3-ylcarbamoyl]-pyrrolidine-1-carbonyl}-propyl)-carbamic acid methyl ester (135 mg, 0.246 mmol), (1-{2-[5-(4-Bromo-phenyl)-1H-imidaz... | {"inputs": {"m1_m2_m6_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "(2-Methyl-1-{2-[4\u2032-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-3-ylcarbamoyl]-pyrrolidine-1-carbonyl}-propyl)-carbamic acid methyl ester"}], "amount": {"mass": {"value": 135.0, "units": "MILLIGRAM"}}, "reaction... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Dissolve 3-phenyl-2-t-butylcarboxymethylpropionic acid, ethyl ester (2.68 g, 9.17 mmol) in ethanol (95%, 60 mL) and water (30 mL). Treat with potassium hydroxide (2.94 g, 52 mmol). Stir at room temperature ... | {"inputs": {"m1_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-phenyl-2-t-butylcarboxymethylpropionic acid, ethyl ester"}], "amount": {"mass": {"value": 2.68, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 60... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of sodium borohydride (1.38 g) in tetrahydrofuran (50 ml) was added boron trifluoride etherate (4.49 ml) in a nitrogen stream with stirring at 0°~5° C. The mixture was stirred at the same co... | {"inputs": {"m7": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethanol"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "boron trifluoride etherate"}], "amount": {"volume": {"value": 4.49, "un... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 3-[3-(dimethylamino)prop-2-enoyl]-5-methoxy-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one (3.41 g, 9.29 mmol) and phenylhydrazine (1.83 mL, 18.6 mmol) in AcOH (25 mL) was refluxed for 2 h. ... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-[3-(dimethylamino)prop-2-enoyl]-5-methoxy-1-[3-(trifluoromethyl)phenyl]pyridazin-4(1H)-one"}], "amount": {"mass": {"value": 3.41, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "phenylhydra... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of Compound (48a) (51 mg, 0.086 mmol) in 5.0 ml of dichloromethane were added 32 mg (0.26 mmol) of dimethylaminopyridine and 9.2 μl (0.13 mmol) of acetyl chloride under ice-cooling, and the mi... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Compound ( 48a )"}], "amount": {"mass": {"value": 51.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 4A (25 mg, 0.043 mmol) in degas sed THF (2 mL) was added tetrakis(triphenylphosphine)palladium (10 mg, 0.009 mmol), K2C3 (18 mg, 0.13 mmol), and 3-bromothiophene (21 mg, 0.13 mmol). The res... | {"inputs": {"m1_m4_m5_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4A"}], "amount": {"mass": {"value": 25.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "K2C3"}], "amount": {"mass": {"value": 18.0, "units": "MILLIGRAM"}}, "reaction_role": "REAC... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
287 mg (0.9 mmol) of tert-butyl 8,8-dimethyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate of step 1.3 were dissolved in 5 mL of dichloromethane and treated with 2.5 mL of triflu... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl 8,8-dimethyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate"}], "amount": {"mass": {"value": 287.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dic... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Phosphorous oxychloride (0.42 g, 2.71 mmol) was added to DMF (0.99 g, 13.57 mmol) at 0° C. The resulting colorless solution was added dropwise to a solution of 2-(4-chloro-phenyl)-1H-indole-4-carboxylic aci... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Phosphorous oxychloride"}], "amount": {"mass": {"value": 0.42, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"mass": {"value": 0.99, "units": "GRAM"}}, "reaction_role": "REA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
30 mg of sodium-tert-butoxide and 12 mg of bis(tert-butylphosphino)palladium(0) were placed in a Smith® vial and the vial flushed with nitrogen. 100 mg (0.22 mmol) of 5-bromo-3-(2-methoxy-phenyl)-1-triisopr... | {"inputs": {"m11": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m7_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "5-bromo-3-(2-methoxy-phenyl)-1-triisopropylsilanyl-1H-pyrrolo[2,... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of Example 48 (300 mg, 0.51 mmol) in ethyl acetate (25 ml) was added 10% Pd/C (10% w/w, 30 mg) and was stirred under H2 (1 atms.) for 18 hr. The Pd/C filtered through celite (1 g) and the filt... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 3-iodobenzyl bromide (Aldrich, 3.2 g, 10.77 mmol) in ethanol (20 mL) was treated with cyclopropyl amine (7 mL, 101.5 mmol) and the resulting reaction mixture was stirred over 3 days at ambient... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-iodobenzyl bromide"}], "amount": {"mass": {"value": 3.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "cyclopropyl amine"}], "amount": {"volume": {"value": 7.0, "units": "MILLILITER"}}, "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A round bottomed flask was charged with palladium on carbon (327 mg, 0.308 mmol) and a stirbar. Ethyl 3-(2-nitrophenylamino)butanoate (776 mg, 3.08 mmol) in 1:1 EtOH:EtOAc (40 mL) was added, and the flask w... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethyl 3-(2-nitrophenylamino)butanoate"}], "amount": {"mass": {"value": 776.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "EtOH"}], "reaction_role": "REACTANT"}, {"identifiers": [{"ty... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Part A. A solution of 2-amino-1H-benzimidazole (5.00 g, 57.5 mmol) and triethylamine (7.50 mL, 53.8 mmol) in ethylene dichloride (150 mL) was treated with a solution of 5-bromovaleryl chloride (5.00 mL, 37.... | {"inputs": {"m1_m2_m4_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-1H-benzimidazole"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 7.5, "units": "MILLILITER... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The compound (111 mg, 0.16 mmol) obtained in Example 1j and the compound (133 mg, 0.17 mmol) obtained in Example 97e were used to give the title compound (180 mg; yield, 73%) as a white solid according to t... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "compound"}], "amount": {"mass": {"value": 111.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "compound"}], "amount": {"mass": {"value": 133.0, "units": "MILLIGRAM"}}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
This compound was synthesized by the reaction of 2-[(5-chloro-1H-indol-3-yl)methyl]-5-methyl-3-(1-methyl-1H-imidazol-2-yl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione and (bromomethyl)cyclobutane using po... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "DMF"}], "reaction_role": "SOLVENT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-[(5-chloro-1H-indol-3-yl)methyl]-5-methyl-3-(1-methyl-1H-imidazol-2-yl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione"}], "reaction_... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a DMF (2.28 ml) solution of tert-butyl[3-(4-hydroxy-2,6-dimethoxyphenyl)-6-methoxypyrazolo[5,1-b][1,3]thiazol-7-yl]carbamate (115 mg, 0.273 mmol) were added potassium carbonate (49.0 mg, 0.355 mmol) and ... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "reaction_role": "SOLVENT"}]}, "m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 2.28, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
From the reaction of 4-nitrophenylhydrazine and ethylbutyrylacetate, 2,4-dihydro-2-(4-nitrophenyl)-5-propyl-3H-pyrazol-3-one is obtained. Subsequent reaction with 2-ethylaniline yields 4-(2-ethylanilinometh... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-nitrophenylhydrazine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethylbutyrylacetate"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"iden... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred mixture of 5.44 grams (0.02 mole) of 3-[(4-bromo-2-emthylphenyl)amino)-3oxopropanoic acid prepared in Example V (Compound No. 97) and 2.31 grams (0.02 mole) of thiophenol in approximately 100 m... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ice"}], "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 25.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m2_m6": {"components":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 300 mg of 6-(6-benzyloxypyrid-2-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in 3 mL of trifluoroacetic acid is stirred at 25° C. for 48 hours and then evaporated to dryness under reduced ... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "6-(6-benzyloxypyrid-2-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "trifluoroacetic acid"}], "amou... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
7-(9-benzyl-3,9-diazabicyclo[4,2,1]non-3-yl)-6-fluoro-1-ethyl-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (963 mg, 2.15 mmoles) was dissolved in 125 ml of methanol that was previously saturated with HCl. ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "Pd/C"}], "amount": {"mass": {"value": 1.25, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m7": {"components": [{"identifier... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 2H-pyrido[3,2-b][1,4]oxazin-3-one (0.75 g, 5 mmol) in DMF (18 mL) was slowly added NBS (1.07 g, 6 mmol) under N2. The mixture was stirred at rt for 16 h. HPLC indicated 75% conversion. More... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2H-pyrido[3,2-b][1,4]oxazin-3-one"}], "amount": {"mass": {"value": 0.75, ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a reaction vessel equipped with a stirrer and a thermometer, 683 parts of water, 11 parts of sodium salt of the sulfuric acid ester of methacrylic acid ethylene oxide adduct (ELEMINOL RS-30, manufactured... | {"inputs": {"m12_m3_m4_m5_m6_m7_m8_m9_m10": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sulfuric acid ester"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methacrylic acid ethylene oxide"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
First, 5.97 g of 4,6-dichloropyrimidine, 12.04 g of 3,5-dimethylphenylboronic acid, 8.48 g of sodium carbonate, 0.34 g of bis(triphenylphosphine)palladium(II) dichloride (Pd(PPh3)2Cl2), 20 mL of water, and ... | {"inputs": {"m1_m2_m3_m6_m11_m10": {"components": [{"identifiers": [{"type": "NAME", "value": "4,6-dichloropyrimidine"}], "amount": {"mass": {"value": 5.97, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3,5-dimethylphenylboronic acid"}], "amount": {"mass": {"value": 12.04,... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 4-ethoxy-5-nitro-4H-1,3-benzodioxine (5.80 g, 25.755 mmol) in ethanol (15 mL) and THF (10 mL) was added 4N HCl in 1, 4-dioxane (20 mL). The mixture was stirred at 60° C. for 6 hrs a... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1_m3_m4_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-ethoxy-5-nitro-4H-1,3-benzodioxine"}], "amount": {"mass": {"value": 5.8, "units": "GRAM"}}, "reaction_role": "REACTANT"},... |
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