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 mixture of but-3-ynyl 4-methylbenzenesulfonate (972 mg) and N-methyl piperazine (482 μL) was heated to 80 C. for 4.5 h, diluted with 1,2-dichloroethane (5 mL) and heated to 70° C. for 18 h. Saturated aq. ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1,2-dichloroethane"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "but-3-ynyl 4-methylbenzenesulfonate"}], "amount": {"mass":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The captioned compound was synthesized from 6-methoxyisophthalamic acid and 2-fluoro-3-trifluoromethylaniline by the same procedure as in the manufacturing method described in step C of Example 1-3-1.
### ... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "6-methoxyisophthalamic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-fluoro-3-trifluoromethylaniline"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}, "outcomes": [{... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Sodium 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-tetrahydrofurfurylthio-3-cephem-4-carboxylate (40 mg) was reacted with iodomethyl pivalate (38 mg), followed by purification, in the same man... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Sodium 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-tetrahydrofurfurylthio-3-cephem-4-carboxylate"}], "amount": {"mass": {"value": 40.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound is prepared in analogy to Example 33a) from (RS)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester and sodium borohydride. Yield: 82% of a colorless solid... | {"inputs": {"m0_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(RS)-1-[4-(3-fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidine-3-carboxylic acid methyl ester"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium borohydride"}], "reaction_role": "REACTANT"}]}}, "conditions": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-(3,4-dimethoxy-5-iodophenyl)-1,3-dioxolane (42) (FIG. 22) (2.80 g, 8.0 mmole), copper cyanide (5.7 g, 32.0 mmole) and dry DMF (50 ml) were stirred under an argon atmosphere for 24 hours at 140° C. The rea... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(3,4-dimethoxy-5-iodophenyl)-1,3-dioxolane"}], "amount": {"mass": {"value": 2.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "copper cyanide"}], "amount": {"mass": {"value": 5.7, "units"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
10 Parts of α,α-bis[2-(diisopropylamino)ethyl]-α-phenylacetamide is dissolved in 130 parts by volume of ethanol and the solution placed in pressure shaker with 1 part of ruthenium dioxide. Hydrogen is intro... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ruthenium dioxide"}], "reaction_role": "CATALYST"}]}, "m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "\u03b1,\u03b1-bis[2-(diisopropylamino)ethyl]-\u03b1-phenylacetamide"}], "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 4-chlorobenzyl cyanide (10 g) and 1,3-dibromopropane (7.5 ml) in dry dimethyl sulphoxide (12 ml) was added dropwise under nitrogen to a stirred mixture of sodium hydride (3.6 g) dispersed in m... | {"inputs": {"m5_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "propan-2-ol"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of NaH (0.006 mol) in 1,4-dioxane (30 ml), 2,4,6-trimethyl-phenol (0.006 mol) was added. The mixture was stirred for 15 minutes at room temperature, and a clear solution formed. 4-[(4-chloro... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 0.5, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "NaH"}], "amount": {"moles": {"value": 0.006, "units": "MOLE"}}, "re... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A suspension of 6-fluoro-2-(2-methoxyphenyl)-3H-quinazolin-4-one (14.0 g, 52 mmol), N,N-dimethylaniline (6.6 mL, 52 mmol), and phosphorus oxychloride (4.8 mL, 52 mmol) in benzene (100 mL) was heated at refl... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ice"}], "amount": {"mass": {"value": 300.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m7": {"components"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound (22 mg) was prepared from 3-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azulene-6-carboxylic acid tert-butyl ester (Example 103, Step B; 0.30 mmol) using chloro-cycloheptane (1.0... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "chloro-cycloheptane"}], "amount": {"moles": {"value": 1.0, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}]}, "m0_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(4-chloro-phenyl)-4,5,7,8-tetrahydro-1H-1,2,6-triaza-azu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Iodoethane (2.75 g) was added to a DMF (40 mL) suspension of methyl 2-hydroxy-4-iodobenzoate (3.27 g) and potassium carbonate (3.25 g), and the mixture was stirred at 60° C. for 24 hours. The reaction mixtu... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Iodoethane"}], "amount": {"mass": {"value": 2.75, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "RE... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 340 mg of the resulting isomer mixture, consisting of 7β-phenoxyacetamido-3-diphenylmethoxy-ceph-2-em-4α-carboxylic acid p-nitrobenzyl ester and 7β-phenoxyacetamido-3-diphenylmethoxy-ceph-3-em... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "7\u03b2-phenoxyacetamido-3-diphenylmethoxy-ceph-2-em-4\u03b1-carboxylic acid p-nitrobenzyl ester"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "7\u03b2-phenoxyacetamido-3-diphenylmethoxy-ceph-3-em-4-car... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
47AKU-38 (242 mg, 1.0 mmol) was dissolved in 5 ml dichloromethane and placed in 50 ml flask. 4-Methoxyphenylacetyl chloride (185 mg, 1.2 mmol) in 10 ml dichloromethane was added. After 16 hrs magnetic stirr... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "47AKU-38"}], "amount": {"mass": {"value": 242.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_r... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Following Example 216, to a well stirred solution of 8-(1H-Pyrazol-4-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid and 1-(pyridin-2-yl)-1,4-diazepane to give 227. MS: (ESI+)=473.1
##... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "8-(1H-Pyrazol-4-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-(pyridin-2-yl)-1,4-diazepane"}], "reaction_role": "REACTANT"}]}}, "conditi... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2.2 g of cis-4-(4-methoxycarbonylcyclohexyloxy)benzoic acid (7.91 mmol, 1 eq.) are placed in 30 mL of dimethylformamide at room temperature. 1.98 g of 5-(3,5-difluorobenzyl)[1.3.4]thiadiazol-2-ylamine (8.70... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "dimethylformamide"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "cis-4-(4-methoxycarbonylcyclohexyloxy)benzoic acid"}], "amoun... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 7-bromo-2-methyl-2,3-dihydro-1,2-benzisothiazol-3-ol 1,1-dioxide (0.34 g, 1.2 mmol) in methylene chloride (20 mL), prepared according to the method described in Example 3 was added PDC (1.4... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "7-bromo-2-methyl-2,3-dihydro-1,2-benzisothiazol-3-ol 1,1-dioxide"}], "amount": {"mass": {"value": 0.34, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "amount": {"volume"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
100 g of 3-phenoxybenzyl 2-(3-chloro-4-ethoxyphenyl)-2-methylpropyl ether and 25 g of 97% potassium hydroxide were added to 300 ml of 1,3-dimethyl-2-imidazolidinone (hereinafter referred to as DMI) and the ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "DMI"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-phenoxybenzyl 2-(3-chloro-4-ethoxyphenyl)-2-methylpropyl ether"}], "amount": {"mass": {"value": 100.0, "units": "GRAM"}}, "react... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To the product of Example 1 (500 mg, 1.155 mmol) was added paraformaldehyde (347 mL, 11.6 mmol) and pyrrolidine (0.243 mL, 2.94 mmol) in EtOH (10 mL)/THF (3 mL). The reaction vessel was sealed and heated to... | {"inputs": {"m1_m2_m3_m5_m9": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 500.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "paraformaldehyde"}], "amount": {"volume": {"value": 347.0, "units": "MILLILITER"}}, ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Diethyl 2-(5-methyl-2-nitro-phenyl)propanedioate (9.50 g, 32.2 mmol) was suspended in glacial acetic acid (40 mL) and warmed until it had dissolved. Hydrochloric acid (40 mL of 6 M solution, 240.0 mmol) was... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 40.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "CH3CN"}], "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"id... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture containing 0.8 mole of 2,4-dihydroxy-benzaldehyde, 0.8 mole of 2-chloro-1-dimethylaminoethane and 1.6 mole of potassium carbonate in 1200 ml of anhydrous methyl ethyl ketone is refluxed for 1 hour... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2,4-dihydroxy-benzaldehyde"}], "amount": {"moles": {"value": 0.8, "units": "MOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-chloro-1-dimethylaminoethane"}], "amount": {"moles": {"value": 0.8, "uni... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A suspension of silver oxide in water was prepared by adding a solution of NaOH (1.76 g, 0.044 mol) in water (100 ml) to an aqueous solution of silver nitrate (7.14 g, 0.042 mol in 100 ml), decanting the su... | {"inputs": {"m2_m6_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "NaOH"}], "amount": {"mass": {"value": 1.76, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "silver nitrate"}], "amount": {"volume": {"value": 100.0, "units": "MILLILITER"}}, "reaction_role": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
20 M of NH3 in H2O(10 mL) was added to a suspension of 1,3-Dibromo-8-chloro-imidazo[1,5-a]pyrazine (1.726 g, 0.007425 mol) in 2-Butanol (7.49 mL, 0.0817 mol). The mixture was heated in an oil bath set at 90... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "NH3"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1,3-Dibromo-8-chloro-imidazo[1,5-a]pyrazine"}], "amount": {"mass": {"value": 1.726, "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 mixture of methyl {[1-bromo-6-(2-phenyl-1,3-thiazol-4-yl)-2-naphthyl]oxy}acetate (217 mg, 0.477 mmol), prepared in the previous step, and 1 N NaOH (716 μL, 0.716 mmol) in 20 mL of THF plus 20 mL of methan... | {"inputs": {"m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "NaOH"}], "amount": {"volume": {"value": 716.0, "units": "MICROLITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4.3 mg of 1-methyl-1H-pyrazole-3-carboxylic acid, 6.0 mg of hydroxybenzotriazole and 8.5 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride were added to a dimethylformamide (0.5 ml) solu... | {"inputs": {"m1_m2_m3_m7_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1-methyl-1H-pyrazole-3-carboxylic acid"}], "amount": {"mass": {"value": 4.3, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydroxybenzotriazole"}], "amount": {"mass": {"value": 6... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 2.03 g of ethyl 4-chloro-1,3-dimethylpyrazole-5-carboxylate and 2.45 g of 4-tertbutylbenzylamine was heated at 200° C. for 4 hours under stirring. After cooling to room temperature, the reactio... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 4-chloro-1,3-dimethylpyrazole-5-carboxylate"}], "amount": {"mass": {"value": 2.03, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-tertbutylbenzylamine"}], "amount": {"mass": {"value": 2... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Synthesized from 3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester using a procedure analogous to that used for Example 50 and substituting benzylthiol as the nu... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-{4-[2-(tert-butoxycarbonyl-heptyl-amino)-ethyl]-phenyl}-2-hydroxy-propionic acid ethyl ester"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "benzylthiol"}], "reaction_role": "REACTANT"}]... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared as described in General Method 1 using 2.7 mL of methyl acetoacetate, 1.1 g of NaH 60% dispersion in oil, 12.5 mL of 2.0M n-butyl lithium in hexane, 5.1 mL of valerophenone a... | {"inputs": {"m5": {"components": [{"identifiers": [{"type": "NAME", "value": "ketone"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "NaH"}], "amount": {"mass": {"value": 1.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m4": {"components": [{"identifiers": [{... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1,3-Dichloroacetone (22.9 g, 180.3 mmol) was added to a solution of 2-amino pyridine (10 g, 106.3 mmol) in acetonitrile (200 ml). The mixture was heated at reflux for 14 h (the reaction was monitored by TLC... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1,3-Dichloroacetone"}], "amount": {"mass": {"value": 22.9, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-amino pyridine"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The reagents which were employed were as follows: FLUMO (fluorescein-morphine conjugate) was 3 × 10-6M in water; antifluorescein, was 5.6 × 10-6M in binding sites, in water, 0.05M phosphate, pH 8.0; antimor... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "fluorescein morphine"}], "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Opiate"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Tris-HCl"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Hydrogenate, at approximately 3 atmospheres, a mixture of 8.3 g. of 4'-nitro-3'-trifluoromethylisobutyranilide in 100 ml. of ethanol containing 0.5 g. of 5% palladium on charcoal. Filter and remove the solv... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4'-nitro-3'-trifluoromethylisobutyranilide"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "palladium on charcoal"}], "reaction_role": "CATALYST"}]}, "m3": {"components": [{"identifiers": [... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of malonamide (5.1 g) and sodium ethoxide (20% ethanol solution, 34.3 g) in methanol (125 mL) was stirred at room temperature for 1 hour. To the mixture was added ethyl 2,2-difluoroacetate (6.31 m... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "reaction_role": "REACTANT"}]}, "m1_m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "malonamide"}], "amount": {"mass": {"value": 5.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3-Iodo-4-methylbenzoic acid (5 g, 19.1 mmol) and HATU (8.71 g, 22.9 mmol) in DMF (25 ml) were stirred at room temperature for 10 minutes. HOBT (2.58 g, 19.1 mmol), cyclopropylamine (1.37 g, 22.9 mmol) and D... | {"inputs": {"m1_m2_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "3-Iodo-4-methylbenzoic acid"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HATU"}], "amount": {"mass": {"value": 8.71, "units": "GRAM"}}, "reaction_role... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
26 ml (0.38 mmol) cyclopropylamine was added dropwise to a solution of 30 g of diketene (0.36 mol) in 300 ml tetrahydrofuran at −5 to 0° C. After 1 h stirring at 0° C. no more starting material was detected... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "cyclopropylamine"}], "amount": {"volume": {"value": 26.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diketene"}], "amount": {"mass": {"value": 30.0, "units": "GRAM"}}, "reaction_ro... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Dimethylaminoethanol (0.89 g; 10 mmol) was dissolved in dry chloroform (20 ml) under ice-cooling, and a solution of methacryloyl isocyanate (1.11 g; 10 mmol) in 1,2-dichloroethane (5 ml) was dropwise added ... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Dimethylaminoethanol"}], "amount": {"mass": {"value": 0.89, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-Methoxy-4-(2-methyl-imidazol-1-ylmethyl)-phenylamine was prepared in an analogous fashion to [(S)-1-(4-Amino-3-methoxy-phenyl)-piperidin-3-yl]-(4-methyl-piperazin-1-yl)-methanone of Example 460c replacing... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(3-Methoxy-4-nitro-benzyl)-2-methyl-1H-imidazole"}], "reaction_role": "REACTANT"}]}, "m0_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "[(S)-1-(4-Amino-3-methoxy-phenyl)-piperidin-3-yl]-(4-methyl-piperazin-1-yl)-methanone"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of Boc-L-HomoSer-OH (10.0 g, 45.6 mmol) in DMF was added sodium hydride (2.74 g, 114 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 mins, and then allyl bromide (6.90 g, 57.0 ... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Boc-L-HomoSer-OH"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "sodium hydride"}], "amount": {"mass": {"value": 2.74, "units": "GRAM"}}, "reaction_role... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A crude product (5.99 g, 25.57 mmols) of methyl 2-benzylidene-3-acetoxypropionate was dissolved in 26 ml of methanol, and 3.53 g (25.5 mmols) of potassium carbonate were added thereto. The mixture was stirr... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "crude product"}], "amount": {"mass": {"value": 5.99, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl 2-benzylidene-3-acetoxypropionate"}], "reaction_role": "REACTANT"}, {"identifiers":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 1.5 g of the product of Example 1, 100 ml of dimethylformamide and 3 g of cuprous cyanide was refluxed for 24 hours and the reaction mixture was taken up in 400 ml of water and 400 ml of ethyl ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 400.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 1.5, "units": "GRAM"}}, "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 75.0 g (0.226 mol) of N-benzyloxycarbonyl-L-phenylalanine chloromethyl ketone in a mixture of 807 mL of methanol and 807 mL of tetrahydrofuran at -2° C., was added 13.17 g (0.348 mol, 1.54 ... | {"inputs": {"m1_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "N-benzyloxycarbonyl-L-phenylalanine chloromethyl ketone"}], "amount": {"mass": {"value": 75.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 807.... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Synthesis of MC810 (FIG. 7). To a solution of palmitoleic acid (cis-9-hexadecanoic acid, 2.00 g, 7.87 mmol, Aldrich Chemical Company) in dichloromethane (75 mL), was added oxalyl chloride (1.72 mL, 19.7 mmo... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "palmitoleic acid"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "oxalyl chloride"}], "amount": {"volume": {"value": 1.72, "units": "MILLILITER"}}, "react... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Oxalyl chloride (10 ml) is added at 0° C. to (2) (5 g; 19 mmol), and the mixture is stirred until the evolution of gas subsides (20 min). The excess oxalyl chloride is removed by distillation in a water-pum... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Oxalyl chloride"}], "amount": {"volume": {"value": 10.0, "units": "M... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 4N solution of HCl in EtOAc (10 mL, 40 mmol) was added to stirred solution of tert-butyl {1-[4-(2-phenyl-9-pyrazin-2-yl[1,2,4]triazolo[4′,3′:1,6]pyrido[2,3-b]pyrazin-3-yl)phenyl]cyclobutyl}carbamate (8-7,... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "solution"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "HCl"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "EtOAc"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared following the procedure described for Example 94, but starting from 4-(5-(1-(2-fluorophenyl)-5-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde, obtain... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(5-(1-(2-fluorophenyl)-5-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl)-1,2,4-oxadiazol-3-yl)benzaldehyde"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-aminocyclohexanecarboxylic acid"}], "am... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 3-hydroxy-1-ethynylbenzene (4.36 g, 37 mmol), benzylbromide (6.95 g, 4.1 mmol) and K2CO3 (10.2 g, 7.4 mmol) in acetanitrile (50 ml) is stirred at room temperature for 24 hr. The insoluble mater... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-hydroxy-1-ethynylbenzene"}], "amount": {"mass": {"value": 4.36, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "benzylbromide"}], "amount": {"mass": {"value": 6.95, "units": "GRAM"}}, "reac... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Trans-4-[(5-Chloro-2-methyl-pyridine-3-carbonyl)-amino]-cyclohexanecarboxylic acid methyl ester (step 1) (2.20 g, 7.08 mmol) was placed in a flask with dry THF (100 ml). This was cooled to 0° C. and lithium... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Trans-4-[(5-Chloro-2-methyl-pyridine-3-carbonyl)-amino]-cyclohexanecarboxylic acid methyl ester"}], "amount": {"mass": {"value": 2.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amo... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 6-bromospiro[3,4-dihydro-1,4-benzoxazine-2,1′-cyclopropane] (3.11 g, 12.9 mmol) in DMF (20 mL) was added potassium carbonate (3.6 g, 26.0 mmol) and benzyl bromide (1.61 mL, 13.6 mmo... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "6-bromospiro[3,4-dihydro-1,4-benzoxazine-2,1\u2032-cyclopropane]"}], "amount": {"mass": {"value": 3.11, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium carbonate"}], "amount": {"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Sodium (469 mg, 20.4 mmol) was added to 25 ml of methanol under nitrogen and allowed to react. The resulting solution was allowed to cool and then 2.14 g (5.0 mmol) of N-(2,6-dichloro-3-methylphenyl)-5,7-di... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "amount": {"volume": {"value": 150.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Sodium"}], "amount": {"mass": {"value": 469.0, "units": "MILLIGR... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
L-Lactic acid (25.2 μl, 0.29 mmol), 1-hydroxybenzotriazole monohydrate (36.7 mg, 0.24 mmol), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (68.8 mg, 0.36 mmol), and triethylamine (50.1 μl, 0.... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride methanol"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3_m4_m7_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "L-Lactic acid"}], "amount": {"volume": {"value": 25.2, "units": "MICROLITER"}}, "reaction_role": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 2-chloro-5-nitroanisole (187 mg, 1 mmol), of 4-methyl-1H-imidazole (335 mg, 4 mmol) and of potassium hydroxide (99 mg, 1.5 mmol) in DMSO (0.86 mL) was stirred for 5 h at 80° C. under an atmosp... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-5-nitroanisole"}], "amount": {"mass": {"value": 187.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-methyl-1H-imidazole"}], "amount": {"mass": {"value": 335.0, "units": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of N-4-Methoxybenzyloxycarbonyl α-methyl β-alanine methyl ester (2.81 g, 10.0 mmol) in 30 mL of 25% aqueous methanol was treated with lithium hydroxide (1.3 equivalents) at room temperature for a... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-4-Methoxybenzyloxycarbonyl \u03b1-methyl \u03b2-alanine methyl ester"}], "amount": {"mass": {"value": 2.81, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "lithium hydroxide"}], "reaction_r... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 1-nitroundecane (38.0 g) and O-trimethylsilylpropynol (24.1 g) in dry benzene (300 ml) was added dropwise a solution of freshly distilled phenylisocyanate (44.9 g) and triethylamine (22.4 g... | {"inputs": {"m1_m2_m5_m3_m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "1-nitroundecane"}], "amount": {"mass": {"value": 38.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "O-trimethylsilylpropynol"}], "amount": {"mass": {"value": 24.1, "units": "GRAM"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of Compound 45 (760 mg, 4.00 mmol) in dry CH2Cl2 (15 ml) was added TiCl4 (1.67 g, 8.80 mmol) via a syringe with ice-cooling. After 15 min, to this was added a solution of dichloromethy... | {"inputs": {"m1_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "Compound 45"}], "amount": {"mass": {"value": 760.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_rol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 1-N-(1-benzyl-piperidin-4-yl)-indole (100 g, 0.344 mol) in methylene chloride (1 L) was added ethyl chloroformate (99.2 mL) dropwise with stirring. The mixture was refluxed for 48 hours, co... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-N-(1-benzyl-piperidin-4-yl)-indole"}], "amount": {"mass": {"value": 100.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl chloroformate"}], "amount": {"volume": {"value": 99.2, "unit... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of L-prolin-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)amide from step 2 (3.90 g, 10.6 mmol, HPLC RT=2.77 min), (2R)-3,3-dimethyl-R-hydroxybutyric acid from step 3 (1.40 g,... | {"inputs": {"m1_m2_m3_m6_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "L-prolin-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)amide"}], "amount": {"mass": {"value": 3.9, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "(2R)-3,3-dimethyl-R-hydroxybu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Prepared similarly to Example 14 from 2-(butyloxy)-8-(methyloxy)-9-[2-(3-piperidinyl)ethyl]-9H-purin-6-amine and iodocyclohexane.
### ORD JSON:
| {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(butyloxy)-8-(methyloxy)-9-[2-(3-piperidinyl)ethyl]-9H-purin-6-amine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "iodocyclohexane"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynami... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared (as described above for the preparation of Example 2) from 1.0 g (2.05 mmol) of Intermediate 45 (as the TFA salt) and 0.86 g (4.2 mmol) of Intermediate 18 to yield 290 mg (25... | {"inputs": {"m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 45"}], "amount": {"mass": {"value": 1.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "TFA"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Interme... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-Bromo-4-tert-butylanisole (4.54 g, 18.67 mmol) was dissolved in acetic anhydride (15 mL) and the solution was cooled to 0° C. A solution of nitric acid (70%, 2.5 mL) in acetic anhydride (2.5 mL) was prepa... | {"inputs": {"m0_m7_m3_m11": {"components": [{"identifiers": [{"type": "NAME", "value": "HNO3"}], "amount": {"volume": {"value": 2.5, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic anhydride"}], "amount": {"volume": {"value": 2.5, "units": "MILLILITER"}}, "react... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 3-methoxy-2-nitro-benzoic acid (11.50 g) in DMF (100 ml) was added N,N′-carbonyldiimidazole (11.35 g) and the reaction mixture was stirred at room temperature for 45 minutes. Methan... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 800.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-methoxy-2-nitro-benzoic acid"}], "amount": {"mass": {"value": 1... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was synthesized from N-isopropyl-6-ethynylpyridazin-3-amine and 4-chloro-3-iodo-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide in a manner similar to that descr... | {"inputs": {"m0_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-isopropyl-6-ethynylpyridazin-3-amine"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-chloro-3-iodo-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide"}], "reaction_role": "REACTAN... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 1.00 g of 1-(4-hydroxybenzyl)-2-butyl-4-chloro-5-hydroxymethylimidazole in 15 mL of DMF at 25° was added 0.185 g of sodium methylate, and the resulting mixture was stirred at 25° for 0.25 h... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "\u03b1-bromo-o-tolunitrile"}], "amount": {"mass": {"value": 0.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "DMF"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_ro... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 3-(4-hydroxymethylphenoxy)propionic acid (4.00 g, 20.40 mmol) in THF (20 mL) is added a solution of LiAlH4 (10 mL, 1 M in THF). The mixture becomes warm and is diluted with THF (20 mL) befo... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(4-hydroxymethylphenoxy)propionic acid"}], "amount": {"mass": {"value": 4.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "LiAlH4"}], "amount": {"volume": {"value": 10.0, "units": "MILLIL... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
6-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidine-4-carbaldehyde (described in Example 1, Step 3) (0.20 g, 0.60 mmol) was dissolved in tetrahydrofuran (6.00 mL) and was cooled to −78° C., the... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "6-(1,4-Dioxaspiro[4.5]dec-8-yloxy)-2-(trifluoromethyl)pyrimidine-4-carbaldehyde"}], "amount": {"mass": {"value": 0.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
N-(2-Dimethylaminoethyl)-N-(2-pyrazinyl)cyanamide (2.83 g., 0.015 mole) is dissolved in 20 ml of 6N hydrochloric acid. After one hour, the mixture is made alkaline with concentrated sodium hydroxide and con... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(2-Dimethylaminoethyl)-N-(2-pyrazinyl)cyanamide"}], "amount": {"mass": {"value": 2.83, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "hydrochloric acid"}], "amount": {"volume": {"value": 20.0... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In 50 ml of absolute ethyl alcohol was dissolved 4.0 g of the 1-(3-piperidinopropyl)-3-(3-diethylaminopropylamino)-5-hydroxyindazole, and into the solution was introduced dried hydrogen chloride gas under c... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrogen chloride"}], "reaction_role": "REACTANT"}]}, "m4_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(3-piperidinopropyl)-3-(3-diethylaminopropylamino)-5-hydroxyindazole"}], "amount": {"mass": {"value": 4.0, "units": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a mixture of 14.62 ml of n-propylmercaptan, 16.3 g of potassium t-butoxide and 400 ml of DMF at 0° C. was added 27.45 g (0.1076 mole) of N-difluoromethyl-N-methyl-2-chlorobenzenesulfonamide in 100 ml of ... | {"inputs": {"m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "n-propylmercaptan"}], "amount": {"volume": {"value": 14.62, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "potassium t-butoxide"}], "amount": {"mass": {"value": 16.3, "units": "GRAM"}}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Following the procedure described for the preparation of trans-3-benzyl-4-(2-hydroxyethyl)-2-azetidinone from 8-oxo-2,2-dimethyl-7α-benzyl-3-oxa-1-azabicyclo[4.2.0]octane and using 8-oxo-2,2-dimethyl-7β-met... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "trans-3-benzyl-4-(2-hydroxyethyl)-2-azetidinone"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "8-oxo-2,2-dimethyl-7\u03b1-benzyl-3-oxa-1-azabicyclo[4.2.0]octane"}], "reaction_role": "REACTANT"}]}, "m3": {"com... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
400 mg (1.01 mmol) of 8-cyano-1-cyclopropyl-7-((1S,6S)-2,8-diazabicyclo[4.3.0]-nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 1.03 ml (10.1 mmol) of ethyl propiolate are heated at 120... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "8-cyano-1-cyclopropyl-7-((1S,6S)-2,8-diazabicyclo[4.3.0]-nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid"}], "amount": {"mass": {"value": 400.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-(Benzyloxy)ethanol (0.75 ml) is dissolved in N,N-dimethylformamide (3 ml), and added dropwise to a solution of sodium hydride (400 mg) in N,N-dimethylformamide under ice-cooling. The mixture is stirred fo... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m1_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(Benzyloxy)ethanol"}], "amount": {"volume": {"value": 0.75, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifi... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of (3-chlorophenyl)methyl 5-{[(3-chlorophenyl)methyl]oxy}-2-methylbenzoate from the preparation of Intermediate 84 described above (2.67 g, 6.66 mmol) in 1,4-dioxane (20 ml) and water (10 ml) was... | {"inputs": {"m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "lithium hydroxide"}], "amount": {"mass": {"value": 419.0, "units": "MILLIGRAM"}}, "reaction_r... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 33.2 g (268 mmoles) dimethyl methylphosphonate (Aldrich) in 360 ml dry tetrahydrofuran was cooled to -78° in a dry nitrogen atmosphere. To the stirred phosphonate solution was added 118 ml of ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 2-phenoxy acetate"}], "amount": {"mass": {"value": 22.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "phosphonate"}], "reaction_role": "REACTANT"}, {"identif... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
LiOH (66 mmol) was added to a solution of ethyl (2S)-2-({[(2,2-dimethylpent-4-en-1-yl)(methyl)amino]carbonyl}amino)non-8-enoate (2.35 g, 6.67 mmol) in MeOH (20 mL), water (10 mL) and THF (30 mL). The reacti... | {"inputs": {"m1_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "LiOH"}], "amount": {"moles": {"value": 66.0, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethyl (2S)-2-({[(2,2-dimethylpent-4-en-1-yl)(methyl)amino]carbonyl}amino)non-8-enoate"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 5-nitroindole (38) (2.0 g, 12.334 mmol) in dry ethanol (20 mL) was treated with pyrrolidine (3.08 mL, 37.002 mmol) followed by N-Boc-4-piperidone (4.91 g, 24.668 mmol) at room temperature and ... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-nitroindole"}], "amount": {"mass": {"value": 2.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyrrolidine"}], "amount": {"volume": {"value": 3.08, "units": "MILLILITER"}}, "reaction_rol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4.484 g of iron powder is added to a solution containing 78 ml of acetic acid and 3.415 g of 6-chloro-3-nitro-2-pyridinamine. The reaction medium is heated at 60° C.-70° C. for 2 hours 45 minutes, then left... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "iron"}], "amount": {"mass": {"value": 4.484, "units": "GRAM"}}, "reaction_role": "CATALYST"}]}, "m5_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ammonium hydroxide"}], "amount": {"volume": {"value": 200.0, "units": "MILLIL... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 3′-hydroxyacetophenone (0.500 g, 3.67 mmol) and imidazole (0.500 g, 7.34 mmol) in CH2Cl2 (5 mL) was added tert-butyldimethylsilyl chloride (0.609 g, 4.04 mmol), and the reaction was stirred... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3\u2032-hydroxyacetophenone"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "imidazole"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reacti... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Polymerisation was performed in the same principle as in Example 9, but the betulin was added to the reaction mixture in three portions during first two hours. The amounts of the ingredients were following:... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "betulin"}], "amount": {"mass": {"value": 25.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
6-Chloro-2-(5-nitro-2-thienyl)-3H-imidazo[4,5-b]pyridine (Example 275) (0.10 g, 0.36 mmol) was dissolved in methanol (10 ml). A catalytic amount of Raney nickel was added. The solution was shaken for 2 h un... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "6-Chloro-2-(5-nitro-2-thienyl)-3H-imidazo[4,5-b]pyridine"}], "amount": {"mass": {"value": 0.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 10.0, "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a mixture of 6-methoxyindole (0.3 g, 2.03 mmol) and anhydrous ZnCl2 (0.56 g, 4.07 mmol) in CH2Cl2 (10 mL), EtMgBr (0.9 ml, 3 M) was added over 10 min at room temperature. The obtained suspension was stir... | {"inputs": {"m1_m7_m5_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "6-methoxyindole"}], "amount": {"mass": {"value": 0.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "CH2Cl2"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_rol... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a manner analogous to example 1 d, the process is carried out by a reaction of 4.1 g (16 mmol) of (4-bromo-2-tert-butylphenyl)dimethylamine with 9.6 ml (24 mmol) of a 2.5M solution of n-butyllithium and ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "n-butyllithium"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(4-bromo-2-tert-butylphenyl)dimethylamine"}], "amount": {"mass": {"value": 4.1, "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 mixture of 13.96 g of a glycine ethyl ester hydrochloride, 30 ml of THF, 10.11 g of triethylamine and 30 ml of DMF, 15.91 g of 2,4-difluoronitrobenzene was added, followed by heating under reflux for 3... | {"inputs": {"m1_m2_m3_m6_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "glycine ethyl ester hydrochloride"}], "amount": {"mass": {"value": 13.96, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 30.0, "units": "MILLILIT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.0366 g, 0.105 mmol) synthesized in Example B1, Step 1 in methanol (2 mL) was added with 1H-pyrazolo... | {"inputs": {"m1_m3_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate"}], "amount": {"mass": {"value": 0.0366, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1H-pyrazo... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-Methoxy-1,4-bis (methoxycarbonyl)benzene (1.61 g, 7.20 mmol) from Step 2 was dissolved in 20 mL of 1:1 THF:H2O and to the stirred solution was added 1N NaOH (7.2 mL, 7.2 mmol). After 24 h, the reaction wa... | {"inputs": {"m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "H2O"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NaOH"}], "amount": {"volume": {"value": 7.2, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m5": {"components": [{"identifiers": [{"type": "NAME",... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 300-ml autoclave equipped with an agitator was charged with 59.2 g of methyl acetate, 104 g of p-cresol, 1.8 g of palladium chloride, 31.5 g of methyl iodide and 5.8 g of triphenylphosphine, and the react... | {"inputs": {"m1_m2_m6_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl acetate"}], "amount": {"mass": {"value": 59.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "p-cresol"}], "amount": {"mass": {"value": 104.0, "units": "GRAM"}}, "reaction_role"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The product of EXAMPLE 160 in MeOH is reacted with ammonium chloride by the method of EXAMPLE 27 to generate the title material.
### ORD JSON:
| {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ammonium chloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "MeOH"}], "reaction_role": "SOLVENT"}]}, "m3": {"compon... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred suspension of lithium aluminum hydride (97 mg, 2.55 mmol) in tetrahydrofuran (5 mL) was added a solution of ethyl [cis-5-amino-1-benzylpiperidin-2-yl]acetate (352 mg, 1.27 mmol, step 7 of Examp... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "lithium aluminum hydride"}], "amount": {"mass": {"value": 97.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 1,4-dioxane (100 mL), 1-methyl-1H-pyrazol-3-amine (970 mg, 10.0 mmol), 3,5-dibromo-1-methyl... | {"inputs": {"m6_m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "1-methyl-1H-pyrazol-3-amine"}], "amount": {"mass": {"value": 970.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3,5-dibromo-1-methylpyridin-2-(1H)-one"}], "amount": {"mass": {"val... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 4-hydroxymethylcyclohexanecarboxylic acid (TCI-JP, 0.50 g, 3.2 mmol) in 10 mL CH3OH was added 0.50 mL concentrated H2SO4. This mixture was warmed to reflux and allowed to stir for 2 h. The reaction mixtu... | {"inputs": {"m1_m4_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-hydroxymethylcyclohexanecarboxylic acid"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "H2SO4"}], "amount": {"volume": {"value": 0.5, "units": "MILLILI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 3-bromo-5-ethoxypyridine (53 g, 262 mmol) in DCM (600 mL) at 0° C. was slowly added m-CPBA (67.9 g, 393 mmol) over 30 min. After the resulting solution was stirred for 15 h, the mixture was... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-bromo-5-ethoxypyridine"}], "amount": {"mass": {"value": 53.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "m-CPBA"}], "amount": {"mass": {"value": 67.9, "units": "GRAM"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared as described in Example 278, substituting isobutyryl chloride for acetyl chloride and N-(isoindolin-5-yl)isoindoline-2-carboxamide for 5-amino-N-(4-(propylcarbamoyl)phenyl)is... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "acetyl chloride"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(isoindolin-5-yl)isoindoline-2-carboxamide"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"ty... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Into a solution of 1,3,5-tribromobenzene (9.0 g, 28.6 mmol) in diethyl ether (200 mL) was added n-butyllithium solution in hexane (2.5 M, 12 mL, 30.6 mmol) dropwise at −78° C. The reaction was stirred at th... | {"inputs": {"m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "chlorotriphenylsilane"}], "amount": {"mass": {"value": 9.27, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "diethyl ether"}], "amount": {"volume": {"value": 90.0, "units": "MILLILITER"}}, "reac... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Using ethyl 4-iodobenzoate (552 mg) and 4,4-dimethylpyrrolidin-2-one (226 mg) and by the reaction and treatment in the same manner as in Preparation Example 48, the title compound (538 mg) was obtained.
##... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 4-iodobenzoate"}], "amount": {"mass": {"value": 552.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4,4-dimethylpyrrolidin-2-one"}], "amount": {"mass": {"value... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was synthesized from 4-(9-cyclohexyl-7-ethyl-7-fluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid as described in the General proced... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "HATU"}], "reaction_role": "REACTANT"}]}, "m0_m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(9-cyclohexyl-7-ethyl-7-fluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Using 5-bromosalicylic acid and 2-amino-5-bromo-4-(trifluoromethyl)thiazole as the raw materials, the same operation as the example 16 gave the title compound. (2-Amino-5-bromo-4-(trifluoromethyl)thiazole: ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5-bromosalicylic acid"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-5-bromo-4-(trifluoromethyl)thiazole"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
An EtOH (75 mL) solution of ethyl 1-phenyl-4-(phenylmethyl)-2-piperazinecarboxylate (2.20 g, 6.8 mmol) and 500 mg of 4% Pd/C was subjected to hydrogenolysis in a standard Parr apparatus. The reaction was ca... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 1-phenyl-4-(phenylmethyl)-2-piperazinecarboxylate"}], "amount": {"mass": {"value": 2.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Pd/C"}], "amount": {"mass": {"v... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
N′-Isopropylidene-hydrazine-carboxylic acid methyl ester (6.45 g) were dissolved in ethanol (50 mL) and acetic acid (50 mL) PtO2 (0.231 g) was added, and reaction was stirred at room temperature for 22 hour... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N\u2032-Isopropylidene-hydrazine-carboxylic acid methyl ester"}], "amount": {"mass": {"value": 6.45, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 50... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Using the conditions of General Procedure E for Amide Coupling in Parallel Mode, 4-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-biphenyl-2,4′-dicarboxylic acid 2-methyl ester (which may be prepared as described f... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "pyrrolidine"}], "amount": {"mass": {"value": 44.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Amide"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"ide... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 4-aminoresorcinol hydrochloride (5.00 g), 4-(cyclopropylmethoxy)-3-fluorobenzoic acid (5.91 g) and diisopropylethylamine (7.37 mL) in DMF (50 mL) was added HATU (11.8 g), and the mixture wa... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3_m5_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-aminoresorcinol hydrochloride"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
2-Bromo-4-(trifluoromethoxy)phenol (Preparation 8; 5 g, 20 mmol) was dissolved in N,N-dimethylformamide (60 ml), and potassium carbonate (5.4 g, 40 mmol) was added, followed by benzyl bromide (3.5 ml, 30 mm... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2-Bromo-4-(trifluoromethoxy)phenol"}], "amount": {"mass": {"value": 5.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide"}], "amount": {"volume": {"value": 60.0, "units": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinoline (compound 116) (84 mg), 4-methoxyphenylboronic acid (152 mg), and tetrakistriphenylphosphine palladium (12 mg) were dissolved in toluene (1 ml) to p... | {"inputs": {"m1_m2_m3_m4_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "4-[(2-Iodo-6-methyl-3-pyridyl)oxy]-6,7-dimethoxyquinoline"}], "amount": {"mass": {"value": 84.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "compound 116"}], "reaction_role": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine 4 (155 mg) and 2-methylbenzimidazole (161 mg) were heated together at 135° C. overnight. The mixture was then cooled, diluted with water and ex... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine"}], "amount": {"mass": {"value": 155.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-methylbenzimidazole"}], "amount": {"mass": {"valu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 2-[4-(4-ethoxycarbonylbenzyl)-1-piperazinyl]-4-phenyl-1-azaspiro[4.5]deca-1,3,6,9-tetraen-8-one (12.4 g) in 1,2,4-trichlorobenzene (250 cc) is heated for 11 hours to a temperature of about 210... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-[4-(4-ethoxycarbonylbenzyl)-1-piperazinyl]-4-phenyl-1-azaspiro[4.5]deca-1,3,6,9-tetraen-8-one"}], "amount": {"mass": {"value": 12.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1,2,4-trich... |
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