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:
Palladium acetate (45 mg, 0.2 mmol), BINAP (62 mg, 0.1 mmol) and cesium carbonate (650 mg, 2 mmol) were suspended in anhydrous 1,4-dioxane (3 ml) under an argon atmosphere and sonicated for 45 minutes. 2-Br... | {"inputs": {"m7": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m8": {"components": [{"identifiers": [{"type": "NAME", "value": "Palladium acetate"}], "amount": {"mass": {"value": 45.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}, "m1": {"compon... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a flask equipped with a stirring blade and a dropping funnel were charged 100 parts of dry methylene chloride and 60 parts of ethylenediamine, and the mixture was stirred in an ice bath. To the solution ... | {"inputs": {"m5_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "aminoethylmethacrylamide hydrochloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl methacry... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To methanol add 4-(3-aminophenyl)-1-(phenylmethyl)-2-piperazinecarboxamide and Pd(OH)2. Place the reaction on a Parr hydrogenator at 50 psi of H2 and shake. Monitor the progress of the reaction by thin-laye... | {"inputs": {"m3_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(3-aminophenyl)-1-(phenylmethyl)-2-piperazinecarboxamide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Pd(OH)2"}], "reaction_role": "CATALYST"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Aluminium(III)chloride (0.666 mol) was added portionwise at RT to a solution of N-phenyl-2-benzothiazolylamine (0.222 mol) and 1,2dichloro-1-propanone (0.233 mol) in 1,2-dichloroethane (500 ml) and the mixt... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Aluminium(III)chloride"}], "amount": {"moles": {"value": 0.666, "units": "MOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N-phenyl-2-benzothiazolylamine"}], "amount": {"moles": {"value": 0.222, "uni... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A stirred solution of 4-[2-(2-carbamoyl-ethyl)-5-phenylpyrrol-1-yl]-benzoic acid tert-butyl ester (3.92 mmol, 1.0 eq.) in dioxane and pyridine was cooled in an ice bath. To the mixture was added Trifluoroac... | {"inputs": {"m1_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-[2-(2-carbamoyl-ethyl)-5-phenylpyrrol-1-yl]-benzoic acid tert-butyl ester"}], "amount": {"moles": {"value": 3.92, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dioxane"}], "reaction_... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound (12 mg) was prepared using 130 mg (0.39 mmol) of 4-benzothiazol-2-yl-5-(3-bromopropyl)-2H-pyrazol-3-ylamine, which was derived from 3-(5-amino-4-benzothiazol-2-yl-1H-pyrazol-3-yl)-propan-... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-benzothiazol-2-yl-5-(3-bromopropyl)-2H-pyrazol-3-ylamine"}], "amount": {"mass": {"value": 130.0, "units": "MILLIGRAM"}}, "reaction_... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Using the general method of Example 10, 2-propylthiazolo[4,5-c]quinolin4-amine (1.75 g) was reacted with 1 equivalent of concentrated hydrochloric acid to provide 2-propylthiazolo[4,5-c]quinolin-4-amine hyd... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-propylthiazolo[4,5-c]quinolin4-amine"}], "amount": {"mass": {"value": 1.75, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "REACTAN... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Except for using 4-formylbenzoic acid (112 mg) in place of 4-(diethoxymethyl)benzaldehyde and using 8-cyclohexyl-2,8-diazaspiro[4.5]decane (170 mg) in place of 8-isobutyl-2,8-diazaspiro[4.5]decane, the same... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-formylbenzoic acid"}], "amount": {"mass": {"value": 112.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "8-cyclohexyl-2,8-diazaspiro[4.5]decane"}], "amount": {"mass... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Bromine (4.62 g) was added in one portion to a stirred solution of 4-trifluoromethylpyrimidin-6-one (4.3 g) and sodium acetate (10.53 g) in acetic acid (43 ml). After stirring for 2 hours, the reaction mixt... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Bromine"}], "amount": {"mass": {"value": 4.62, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-trifluoromethylpyrimidin-6-one"}], "amount": {"mass": {"value": 4.3, "units": "GRAM"}}, "re... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
5-[N-(2-Butyl)-sulfamoyl]-isatoic anhydride, which is to be used as the starting material, can be obtained, for example, in a manner analogous to that described in Example 1, using 2-chloro-5-chlorosulfonyl... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-[N-(2-Butyl)-sulfamoyl]-isatoic anhydride"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-5-chlorosulfonylbenzoic acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"condi... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Following the procedure described in EXAMPLE 10.47, and making non-critical variations using spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 4′-bromospiro[furo[2,3-f][1,3]benzodioxole-... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(bromomethyl)-5-(trifluoromethyl)furan"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "spiro[furo[2,3-f][1,3]benzodioxole-7,3\u2032-indol]-2\u2032(1\u2032H)-one"}], "reaction_role": "REA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared according to the procedure of Intermediate 24 from 2.28 g (15.6 mmol) of 1,4-dioxa-8-aza-spiro[4.5]decane and 2.85 g (13.0 mmol) of 4-fluoro-N-(2-hydroxyethyl)-benzenesulfona... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-fluoro-N-(2-hydroxyethyl)-benzenesulfonamide"}], "amount": {"mass": {"value": 2.85, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 24"}], "reaction_role": "R... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A modification of the general method described in Part C of Example 3 was used to treat 7-benzyloxy-2-butyl-5-oxido-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline (1.0 g, 2.1 mmol). An analysis by TLC indica... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium methoxide"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "7-benzyloxy-2-butyl-5-oxido-1-(2-phenoxyethyl)-1H-imidazo[4,5-c]quinoline"}], "amount": {"mass": {"value": 1.0, "units": "G... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of ethyl N-(b-ethoxycarbonylethyl)-N-(4-methoxyphenyl)glycinate (106.7 g, 0.345 mol) in dry benzene (400 mL) is added to a mixture of ethanolic sodium ethoxide in benzene (prepared by dissolving ... | {"inputs": {"m1_m5_m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl N-(b-ethoxycarbonylethyl)-N-(4-methoxyphenyl)glycinate"}], "amount": {"mass": {"value": 106.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium ethoxide"}], "reaction_role": "R... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of L-tyrosyl-N-methyl-N-(3-phenylpropyl)-D-methioninamide monohydrochloride (1.3 g.) and aqueous hydrogen peroxide (3%, 2.7 ml.) in acetic acid (10 ml.) was stirred at room temperature for two ho... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "L-tyrosyl-N-methyl-N-(3-phenylpropyl)-D-methioninamide monohydrochloride"}], "amount": {"mass": {"value": 1.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrogen peroxide"}], "amount": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared as described for 4-hydroxy-6-(2-phenethyl)pyridazin-3(2H)-one (Example 1) from 3,4-bis(benzyloxy)-6-[(3-chloromethyl)phenyl)ethynyl]pyridazine (Intermediate 24) except that the reaction was carried... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-hydroxy-6-(2-phenethyl)pyridazin-3(2H)-one"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 500 mg of sodium 7-[2-(2-aminothiazol-4-yl)-2-ethoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylate in 5 ml of N,N-dimethylacetamide were added, with ice-cooling, 395 mg of 1-iodoeth... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium 7-[2-(2-aminothiazol-4-yl)-2-ethoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylate"}], "amount": {"mass": {"value": 500.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4-Chloro-6,7-dimethoxyquinoline (111 mg), 5-tert-butyl-2-hydroxybenzaldehyde (356 mg), and 4-dimethylaminopyridine (244 mg) were suspended in monochlorobenzene (2 ml), and the suspension was stirred at 130°... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-dimethylaminopyridine"}], "amount": {"mass": {"value": 244.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Chloro-6,7-dimethoxyquinoline"}], "amount": {"mass": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 1-[2-(tertbutyldimethylsilanyloxy)ethyl]-N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropanesulfonamide (20 mg, 0.032 mmol) in THF (2 mL) at 0° C. is a... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-[2-(tertbutyldimethylsilanyloxy)ethyl]-N-(4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropanesulfonamide"}], "amount": {"mass": {"value": 20.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
100 ml of methanol, 80 ml of acetone and 0.3 ml of concentrated hydrochloric acid were added to 5.5 g (10.0 mmol) of N1-(4-sulfamoylbenzyl)-N5-dodecyl-biguanide dihydrochloride. The mixture was refluxed for... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 0.3, "units": "MILLILITER"}}, ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of Hunig's base (286 μl, 1637 μmol), HATU (830 mg, 2182 μmol) and cyclohexanecarboxylic acid (147 mg, 1146 μmol) was dissolved in 2.0 mL CH2Cl2 and stirred at room temperature for 10 min. 6-bromob... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "6-bromobenzo[d]thiazol-2-amine"}], "amount": {"mass": {"value": 250.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Hunig's base"}], "amount": {"volume": {"val... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-(6-Chloropyridin-3-yl)-N-(5-(3-fluorophenyl)pyridin-2-yl)acetamide 140-1 (100 mg, 0.29 mmol) was heated with 1-(piperazin-1-yl)ethanone (0.8 ml) at 108° C. for 4 hours. The mixture was dissolved in EtOAc ... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(6-Chloropyridin-3-yl)-N-(5-(3-fluorophenyl)pyridin-2-yl)acetamide"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-(piperazin-1-yl)ethanone"}], "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 11.37 g (50 mmol) of (Z)-N,N-diethyl-3,7-dimethyl-2,6-octadienylamine, 101.5 mg (0.25 mmol) of bis[η4 -(Z,Z)-1,5-cyclooctadiene]rhodium(I) tetrafluoroborate, 160 mg (0.275 mmol) of (R)-(6,6'-di... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(Z)-N,N-diethyl-3,7-dimethyl-2,6-octadienylamine"}], "amount": {"mass": {"value": 11.37, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "bis[\u03b74 -(Z,Z)-1,5-cyclooctadiene]rhodium(I) te... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was synthesized in analogy to (4-cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine (described in example S53) using 1,1-dimethylindan-5-carbaldehyde (prepared as descr... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium borohydride"}], "amount": {"mass": {"value": 32.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(4-cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-et... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 500 mg of 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine in 3 ml of methylene chloride, cooled to 0° C., under argon, is added 346 μl of triethylamine follow... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2-methyl-5-fluorobenzoyl chloride"}], "amount": {"mass": {"value": 340.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "amount": {"volume": {"value": 2.0, "units":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 2,4-dichloropyrimidine (0.15 g, 1.0 mmol), benzylamine (0.109 ml, 1.0 mmol) in THF was added DIPEA (0.526ml, 3.0 mmol) and the reaction was heated at reflux for 2 hours resulting in formati... | {"inputs": {"m1_m2_m5_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2,4-dichloropyrimidine"}], "amount": {"mass": {"value": 0.15, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzylamine"}], "amount": {"volume": {"value": 0.109, "units": "MILLILITER"}},... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1,1-Dimethylethyl 4-{4-[(3-chloropropyl)oxy]phenyl}-1-piperazinecarboxylate (D9) (1.6 g), was dissolved in 2-butanone (10 ml). Potassium carbonate (1.38 g) and a catalytic amount of potassium iodide were ad... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-methylpiperidine"}], "amount": {"mass": {"value": 0.99, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m2_m3": {"components": [{... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Triphenylphosphine (6.5 g, 25 mmol) was added to a solution of 4-[[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]-methyl]benzenemethanol (3.0 g, 12.4 mmol) and carbon tetrabromide (8.3 g. 25 mmol) in diethyl ether... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Triphenylphosphine"}], "amount": {"mass": {"value": 6.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-[[2-(1,1-dimethylethyl)-2H-tetrazol-5-yl]-methyl]benzenemethanol"}], "amount": {"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropyl-amide (284) (430 mg, 0.69 mmol) in tetrahydro... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 7.48 g. (17.6 mM) quantity of (αS,5S) 2-[(benzyloxy)carbonyl]-3-oxo-α-phthalimido-5-isoxazolidine acetic acid is dissolved in 150 ml. of ethyl acetate and 75 ml. of 95% ethanol. The solution is treated wi... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(\u03b1S,5S) 2-[(benzyloxy)carbonyl]-3-oxo-\u03b1-phthalimido-5-isoxazolidine acetic acid"}], "reaction_role": "REACTANT"}]}, "m2": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In methanol (284 ml) is suspended 2',3',4'-trichloroacetophenone (94.7 g), and thereto is added sodium borohydride (7.6 g) at 15° C.-25° C. The mixture is stirred at 25° C. for two hours, and evaporated to ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2',3',4'-trichloroacetophenone"}], "amount": {"mass": {"value": 94.7, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium borohydride"}], "amount": {"mass": {"value": 7.6... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 5 parts of 1-(3-methylphenyl)piperazine dihydrochloride, 10.6 parts of sodium carbonate and 180 parts of N,N-dimethylformamide was stirred for 1 hour at 65° C. Then there were added 7.2 parts o... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(3-methylphenyl)piperazine dihydrochloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "s... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Dinitrotetraphenylporphyrin (2.0 g 2.83 m mol) was added to a hydrogenation flask (500-ml) and dissolved in dry toluene (200-ml). To this solution was added the catalyst about 10% ruthenium on alumina pelle... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Dinitrotetraphenylporphyrin"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "toluene"}], "reaction_role": "SOLVENT"}]}, "m3_m4": {"compo... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-methylisoindoline-1,3-dione was prepared by the procedure of Example 8 from 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine (1.4 g, 5.0 mmol)... | {"inputs": {"m0_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamine"}], "amount": {"mass": {"value": 1.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-methylphthalic anhydride"}], "amount": {"mas... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
By substituting methylthiomethyl chloride for the dimethylaminopropyl chloride in the procedure of Example 4 and substituting the 2-methyl-4H-pyrazolo[1,5-a]pyrazolo-[4',3':5,6]pyrido[3,4-e]pyrimidin-5(8H)-... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "8-ethyl-2-methyl-4H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]-pyrido[3,4-e]pyrimidin-5(8H)-one"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "methylthiomethyl chloride"}], "reaction_role": "REAC... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
N-[2-(3amino-4-methoxyphenyl]ethyl]-2,2,2-trifluoro acetamide (26.2 g., 0.1 mole) and iodomethane (14.0 g., 6.2 ml , 0.1 mole) in dry dimethylformamide (500 ml) were stirred under nitrogen for 3 hr. The sol... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N-[2-(3amino-4-methoxyphenyl]ethyl]-2,2,2-trifluoro acetamide"}], "amount": {"mass": {"value": 26.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "iodomethane"}], "amount": {"volume": {"val... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of methyl 2-methyl-2-(6-methyl-5-phenyl-2, 3-dihydro-4-oxo-4 H-1,3-oxazin-3-yl)-butyrate (1.91 g) in 20 ml of ethanol was added at room temperature 30 ml of aq. NaOH (0.3N). After stirring for... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 2-methyl-2-(6-methyl-5-phenyl-2, 3-dihydro-4-oxo-4 H-1,3-oxazin-3-yl)-butyrate"}], "amount": {"mass": {"value": 1.91, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NaOH"}], "amount":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
100 mg (274 μmol) of 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-fluorobutanoic acid (racemate), 53.0 mg (274 μmol) of tert-butyl 4-aminobenzoate, 39.0 mg (274 μmol) of Oxima and 43.0 μ... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-4-fluorobutanoic acid"}], "amount": {"mass": {"value": 100.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tert-butyl... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
20 g of ethyl 4-nitrophenylacetate are dissolved in 30 ml of DMF and added dropwise to a suspension of 4 g of sodium hydride in 20 ml of DMF with ice-cooling. 8.5 ml of dibromoethane are subsequently added,... | {"inputs": {"m6_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ice"}], "amount": {"mass": {"value": 200.0, "units": "GRAM"}}, "reaction_role": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Into a 50-mL 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, were placed a solution of 2-hydroxy-6-methyl-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde (300 mg, 1.27 m... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Tf2O"}], "amount": {"mass": {"value": 720.0, "units": "MILLI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Formic acid (0.29 g, 6.22 mmol) and purified water (5 ml) were added to ethyl 4-(2-amino-4-ethoxycarbonylphenyl)piperazine-1-carboxylate (2.0 g, 6.22 mmol) prepared in the Step 38-1-2. A 30% hydrogen peroxi... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "reaction_role": "REACTANT"}]}, "m5_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrogen peroxide"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Formic acid"}], "amoun... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Example 8 was prepared in an analogous manner to Example 1 using a mixture of Intermediate 3 (0.025 g) and (2-isocyanatoethyl)benzene (18.9 μl) to give the title compound (0.0312 g). LC-MS (System A): Rt 2.... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 3"}], "amount": {"mass": {"value": 0.025, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(2-isocyanatoethyl)benzene"}], "amount": {"volume": {"value": 18.9, "units": "MICROLITER"}}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4-Bromothiophene-2-carbaldehyde (1.9 g, 10 mmol) was dissolved in 40 mL of t-BuOH and 4 mL of 2-methyl-2-butene. The reaction mixture was cooled to 0° C. and NaClO2 (1.1 g, 12 mmol) dissolved in 12 mL of 1M... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-methyl-2-butene"}], "amount": {"volume": {"value": 4.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Bromothiophene-2-carbaldehyde"}], "amount": {"mass": {"va... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 1-benzyloxy-2,3-difluoro-4-nitrobenzene (14 g, 52.8 mmol) and Pd/C (10%, 1.4 g) in MeOH (200 mL) was stirred under a hydrogen atmosphere (30 psi) for 2 h. The catalyst was removed by filtration... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-benzyloxy-2,3-difluoro-4-nitrobenzene"}], "amount": {"mass": {"value": 14.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "MeOH"}], "amount": {"volume": {"value": 200.0, "units": "MILLILI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2 g of tert-butyl 4-[cis-3-(tert-butyl-diphenylsilanyloxy)cyclohexyl]-2,2-dimethylbutyrate are dissolved in 10 ml of tetrahydrofuran, and 8 ml of a 1 M solution of tetrabutylammonium fluoride and tetrahydro... | {"inputs": {"m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrabutylammonium fluoride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "reaction_role": "SOLVE... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3,5-Dibromopyridine (30.5 g, 0.12 mol) was dissolved in dichloromethane (80 mL) and methlytrioxorhenium (150 mg, 0.603 mmol) was added 30% hydrogen peroxide (27 mL) was added slowly over 5 minutes and the m... | {"inputs": {"m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrogen peroxide"}], "amount": {"volume": {"value": 27.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methlytrioxorhenium"}], "amount": {"mass": {"value": 150.0, "units": "MILLIGRAM"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-2-yl)phenyl)urea (0.0506 g, 0.132 mmol) and 3-chloropyrazine-2-carbonitrile (0.0338 g, 0.242 mmol) were combined then added dry N,N-Dimeth... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "N,N-Diisopropylethylamine"}], "amount": {"volume": {"value": 0.0456, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-Ethyl-3-(4-(4-morpholino-5,6,7,8-tetrahydr... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To CuCN (26.9 g, dried in advance under vacuum) was added under nitrogen atmosphere about 500 ml of dry tetrahydrofuran. The mixture was kept at −78□, and 100 ml of methyl magnesium bromide (3.0M diethyleth... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "amount": {"volume": {"value": 50.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethyl 2-bromomethylacrylate"}], "amount": {"mass": {"valu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 0.67 g (2.0 mmol) of methyl 6-benzyloxy-5-nitro-indole-2-carboxylate, 60 ml of tetrahydrofuran and 0.1 g of 10% Pd/C catalyst is hydogenated for 5 h. The catalyst is filtered off and the filtra... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 6-benzyloxy-5-nitro-indole-2-carboxylate"}], "amount": {"mass": {"value": 0.67, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Pd/C"}], "amount": {"mass": {"value": 0.1, "units": "GRA... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
208 g anthraquinone are nitrated with 2.32 kg of 95 % strength nitric acid (molar ratio 35:1) at 25°C during 1.5 hours. The reaction is stopped by distilling off 1.74 kg of 94 % strength nitric acid (molar ... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "anthraquinone"}], "amount": {"mass": {"value": 208.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "nitric acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": tr... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3-((4-aminophenyl)amino)-5-((4-hydroxybenzyl)amino)-1H-pyrazole-4-carboxamide (100 mg) was dissolved in 3.0 mL of DMF and TEA (125 μL, 3.0 eq.) was then added to the reaction vessel. Reaction was then stirr... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3-Chloro-6-fluorobenzo[b]thiophene-2-carbonyl chloride"}], "amount": {"mass": {"value": 75.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 2.0, "un... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of (S)-3-(4-amino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester from Route J step 7 (0.958 g, 1.88 mmol), in anhydrous methylene chloride (20 mL) at 0° C. was ad... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-3-(4-amino-2-benzyloxy-benzenesulfonylamino)-4,4-diethoxy-butyric acid tert-butyl ester"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"volume": {"value": 1.32, "units": "M... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
(2S)-3-[4-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester from Example 173, Step A wag treated with (4-Hydroxy-phenyl)-naphthalen-1-yl-methanone from Step A under the Standard Procedure J. Th... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(2S)-3-[4-(3-Bromo-propoxy)-phenyl]-2-methoxy-propionic acid ethyl ester"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(4-Hydroxy-phenyl)-naphthalen-1-yl-methanone"}], "reaction_role": "REACTANT"}]}, "m3": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Then, 2.6 M n-butylithium hexane solution (1.6 mL) was added to a mixture of 1-bromo-4-ethoxy-2-methylbenzene (0.94 g, 4.37 mmol) and tetrahydrofuran (12 mL) at −78° C. After stirred for one hour, the mixtu... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "reaction_role": "REACTANT"}]}, "m5_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2,3,4,6-tetra-O-benzyl-1-C-(4-chloro-3-formylphenyl)-5-thio-D-glucopyranose"}], "amount": {"mass": {"value": 1.52, "uni... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of 5-bromo-pyridine-3-carbaldehyde (10.0 g, 53.7 mmol) in MeOH (100 mL) was added sodium borohydride (2.2 g, 59.1 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour before i... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "EtOAc"}], "reaction_role": "SOLVENT"}]}, "m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "5-bromo-pyridine-3-carbaldehyde"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifier... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
6-Chloro-N-(1-ethyl-1H-indol-6-yl)-nicotinamide was prepared from 1-ethyl-1H-indol-5-ylamine (prepared as described in J. Med. Chem. 2007, 5509), and 6-chloronicotincyl chloride in a procedure similar to th... | {"inputs": {"m0_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-ethyl-1H-indol-5-ylamine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloride"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "6-chloro-N-(4-Iodo-3... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
(R)-N-Boc-2-Ethynyl-pyrrolidine was prepared according to Method X above by the treatment of (R)-N-Boc-2-formyl-pyrrolidine (700 mg, 3.51 mmol) (Example 89A) with potassium tert-butoxide (510 mg, 4.56 mmol)... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-N-Boc-2-formyl-pyrrolidine"}], "amount": {"mass": {"value": 700.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium tert-butoxide"}], "amount": {"mass": {"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2,2,2-Trifluoro-N-(6-fluoro-imidazo[1,2-a]pyridin-2-yl)-acetamide (compound c, 6 g, 0.02 mol), 2-bromo-1,3-benzothiazole (6.8 g, 32 mmol), potassium carbonate (7000 mg, 0.05 mol), and triphenylphosphine (10... | {"inputs": {"m7": {"components": [{"identifiers": [{"type": "NAME", "value": "palladium acetate"}], "amount": {"mass": {"value": 500.0, "units": "MILLIGRAM"}}, "reaction_role": "CATALYST"}]}, "m1_m2_m3_m4_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "2,2,2-Trifluoro-N-(6-fluoro-imidazo[1,2-a]pyrid... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To (±)-N-(t-butoxycarbonyl)-1,3,4,10b-tetrahydro-7-chloro-9-methoxy-pyrazino[2,1-a]isoindol-6(2H)-one (20 mg, 0.06 mmol) was added concentrated hydrochloric acid (1 mL). After 15 min, the resulting solution... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(\u00b1)-N-(t-butoxycarbonyl)-1,3,4,10b-tetrahydro-7-chloro-9-methoxy-pyrazino[2,1-a]isoindol-6(2H)-one"}], "amount": {"mass": {"value": 20.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound, white solid (28 mg, 69.5%), MS (ISP) m/z=493.3 [(M+H)+], was prepared in accordance with the general method of example 1 from Trans-4-[2-(4-Benzo[1,3]dioxol-4-yl-piperidin-1-yl)-ethyl]-c... | {"inputs": {"m0_m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "solid"}], "amount": {"mass": {"value": 28.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Trans-4-[2-(4-Benzo[1,3]dioxol-4-yl-piperidin-1-yl)-ethyl]-cyclohexylamine hydrochlorid... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared from the product of step A and (E)-1-hexeneboronic acid according to general procedure 2 providing the title compound (47 mg, 53%) as a brown solid; 1H NMR (500 MHz, CD3OD) δ 8.46-8.44 (m, 2H), 7.6... | {"inputs": {"m1_m2_m0": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(E)-1-hexeneboronic acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{"products": [{"identifiers... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
6.4 g (39 mmol) of N-phenylpiperazine (III) is placed in 2.2 mL of glacial acetic acid, heated to 125° C., then 3.2 g (15 mmol) of 2-ethylsulfanyl-6,7-dihydrothieno[3,2-d]pyrimidin-4-ol (II) is added, and t... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 2.2, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "N-phenylpiperazine"}], "amount": {"mass": {"value": 6.4, "units": "G... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of [4-({[2-(benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-3-fluoro-phenoxy]-acetic acid methyl ester (0.40 g, 0.88 mmol) in tetrahydrofuran (10 mL) and methanol (2 mL) ... | {"inputs": {"m1_m3_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "[4-({[2-(benzo[1,3]dioxol-5-yloxy)-pyridine-3-carbonyl]-amino}-methyl)-3-fluoro-phenoxy]-acetic acid methyl ester"}], "amount": {"mass": {"value": 0.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 7.6 g (E)/(Z)-2-[(3-fluoro-2-methyl-phenyl)-hydrazono]-propionic acid ethyl ester and 8.2 g p-toluenesulfonic acid (dried by azeotropic distillation with toluene) was heated 1 h at reflux in to... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bicarbonate"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "( E )"}], "amount": {"mass": {"value": 7.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"typ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 4-[3-[4-[bis(4-fluorophenyl)methyl]-1-piperidinyl]-propoxy-3-methoxybenzoic acid methyl ester (18.58 g, 0.0365 mole) in 400 ml of ethanol was heated for 6 hr at reflux with potassium hydroxide... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-[4-[bis(4-fluorophenyl)methyl]-1-piperidinyl]-propoxy-3-methoxybenzoic acid methyl ester"}], "amount": {"mass": {"value": 18.58, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "am... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
N′-(4-iodobenzoyl)-3-methoxybenzohydrazide (7.0 g, 17.67 mmol) was suspended in POCl3 (40.0 ml) and heating was started. The reaction was kept at 100° C. During heating white solid of starting materials dis... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "N\u2032-(4-iodobenzoyl)-3-methoxybenzohydrazide"}], "amount": {"mass": {"value": 7.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "amount": {"volume": {"va... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of p-toluenesulphonic acid (0.8 g) in IPA (12 mL) at 40° C. was added (5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione(−)-O,O′-dibenzoyl-L-tartrate (2.0 g, d.e. >99%... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "p-toluenesulphonic acid"}], "amount": {"mass": {"value": 0.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(5R)-5-{4-[2-(5-ethylpyridin-2-yl)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione(\u221... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To an ice-cold solution of H2SO4 (150 mL) in water (250 mL), 2-ethyl-6-methylaniline (15.0 g, 111 mmol) is added. The solution is treated with ice (150 g) before a solution of NaNO2 (10.7 g, 155 mmol) in wa... | {"inputs": {"m1_m2_m8_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ice"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "H2SO4"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-et... |
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