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Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of fluoro-diphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester [Example 109(i)] (0.034 g, 0.1 mmol) in DMSO (0.25 ml) is added bromo-acetic acid phenyl ester (0.071 ml, 0.5 mmol). The... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "fluoro-diphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester"}], "amount": {"mass": {"value": 0.034, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "bromo-acetic acid phenyl ester"}],... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a 200-ml eggplant-shaped flask were charged 4.57 g (60 mmol) of 1,2-propylene glycol, 15.86 g (132 mmol) of 2-mercaptoisobutanoic acid, 1.20 g (6.3 mmol) of p-toluenesulfonic acid monohydrate, and 100 g ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4A"}], "reaction_role": "REACTANT"}]}, "m1_m2_m3_m6": {"components": [{"identifiers": [{"type": "NAME", "value": "1,2-propylene glycol"}], "amount": {"mass": {"value": 4.57, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
250 mg (0.81 mmol) of 2-Hydroxy-2-thien-2-ylpent-4-enoic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl ester, Intermediate I-3, were dissolved In 5 ml of acetonitrile and 7.5 ml of chloroform. To this solution were... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 7.5, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "2-Hydroxy-2-thien-2-ylpent-4-enoic acid (3R)-1-azabicyclo[2.2.2]oc... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
1.2 g of the product from example 22 in 15 ml of dry DMF was added in portions to a solution of pyridinium dichromate (4.4 g) in 30 ml of dry DMF. The solution was stirred at room temperature for 24 hours, ... | {"inputs": {"m1_m4_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 1.2, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "pyridinium dichromate"}], "amount": {"mass": {"value": 4.4, "units": "GRAM"}}, "reaction_role"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Compound 561 was prepared according to the procedure described in Scheme IV from 5-amino-1-(4-aminophenyl)benzimidazole and indole-6-carboxylic acid. [M+H]+ calcd for C31H22N6O2: 511.19; found: 511.01.
###... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5-amino-1-(4-aminophenyl)benzimidazole"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "indole-6-carboxylic acid"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a cooled (ice/water) solution of 4.2 g. of 2-ethylthio-4,5-diphenyl-oxazole pre-dissolved in 30 ml. of methylene chloride is added in portions over 5 minutes, 30 g. of m-chloro-peroxybenzoic acid. Examin... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sulfinyl"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ice water"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-ethylthio-4,5-dip... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of {6-[3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenylcarbamoyl]-pyridin-3-yl}-carbamic acid tert-butyl ester (1.21 g, 2.37 mmol) in dioxane (15 mL) is cooled to 0° C. and HCl 4M in dioxane... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "{6-[3-(4-tert-butylcarbamoyl-piperidin-1-ylmethyl)-phenylcarbamoyl]-pyridin-3-yl}-carbamic acid tert-butyl ester"}], "amount": {"mass": {"value": 1.21, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "val... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4-Fluorobenzenecarbothio-amide (250 mg, 1.61 mmol) and 2-bromo-1-pyridin-2-ylethanone hydrobromide (450 mg, 1.61 mmol) were dissolved in DMF (2 mL), and triethylamine (0.23 mL, 1.61 mmol) was added. The rea... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-Fluorobenzenecarbothio-amide"}], "amount": {"mass": {"value": 250.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-bromo-1-pyridin-2-ylethanone hydrobromide"}], "amount": {"mass": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 20 ml of dimethylformamide, 1.99 g of bromoacetophenone, 0.69 g of triazole, and 2 g of potassium carbonate were added, and the mixture was allowed to react at room temperature for 16 hours. The reaction... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "dimethylformamide"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "bromoacetophenone"}], "amount": {"mass": {"value": 1.99, "units": "GRAM"}},... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The product from Example 11B (0.48 g, 1.40 mmol) in CH2Cl2 (20 mL) was treated with TFA (20 mL) and stirred for 1 hour. The mixture was concentrated under reduced pressure and the residue was purified by fl... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "product"}], "amount": {"mass": {"value": 0.48, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "TFA"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a slurry of N-(3-{(3β)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)-6-[(2,4-dinitrophenyl)amino]hexanamide (19, 164 mg, 0.180 mmol) and K2CO3 (270 mg, 1.954 mmol) in N,N-dimethylformamide (20 ... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(3-{(3\u03b2)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)-6-[(2,4-dinitrophenyl)amino]hexanamide"}], "amount": {"mass": {"value": 164.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "N... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To the mixture of 2-bromoanisole (0.020 ml, 0.16 mmol) and 1,4-dioxane (2 ml), water (0.2 ml), cesium carbonate (0.32 g, 0.97 mmol), sodium 1,3-dioxo-1,3-dihydro-isoindole-2-ylmethyl trifluoroborate (81 mg,... | {"inputs": {"m2_m12_m11_m3_m4_m7_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2-bromoanisole"}], "amount": {"volume": {"value": 0.02, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "cesium carbonate"}], "amount": {"mass": {"value": 0.32, "units": "G... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
26.1 g (0.30 mol) of morpholine were added to 24.0 g (0.30 mol) of a 37% aqueous formaldehyde solution in 180 ml of ethanol. Then 30.4 g (0.20 mol) of 4-hydroxy-3-methoxybenzaldehyde (vanillin) were added. ... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "morpholine"}], "amount": {"mass": {"value": 26.1, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "formaldehyde"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "et... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 2 mmol of the compound obtained in Step 4 in 50 ml of ethanol is treated with 2.2 mmol of sodium borohydride for 24 hours. The solvent is evaporated off under reduced pressure and the residue ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "compound"}], "amount": {"moles": {"value": 2.0, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a cooled (-70° C.) and stirred solution of trimethyl phosphonoacetate (1.5 g) in anhydrous tetrahydrofuran (40 ml) was added potassium bis(trimethylsilyl)amide (0.5M in toluene; 15.07 ml) at such a rate ... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3-(tert-butyloxycarbonylamino)cyclobutan-1-one"}], "amount": {"mass": {"value": 1.27, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "tetrahydrofuran"}], "amount": {"volume": {"value": 10.0, "un... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In analogy to the procedure described in example 58D, 3-[benzyloxycarbonyl-((R)-1-methyl-2-oxo-ethyl)-amino]-propionic acid tert-butyl ester and (S)-2-amino-4-benzyloxy-butyric acid methyl ester hydrochlori... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "3-[benzyloxycarbonyl-((R)-1-methyl-2-oxo-ethyl)-amino]-propionic acid tert-butyl ester"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-2-amino-4-benzyloxy-butyric acid methyl ester hyd... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 1.73 g (10.8 mmol) of the bis-iodoethoxyhydroxybenzaldehyde from Example 8 was added diethyl malonate, 2.1 g (4.6 mmol), and this mixture was heated on a steam bath. When the mixture had become homogeneo... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "SOLVENT"}]}, "m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "bis-iodoethoxyhydroxybenzaldehyde"}], "amount": {"mass": {"value": 1.73, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identi... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 5g (17.7mmol) of 1-n-dodecylazacycloheptan-2-one in 150ml of benzene was added 4.18g (9.4mmol) of phosphorus pentasulfide and the mixture was refluxed for 1 hr. After cooling to room temper... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "5g"}], "amount": {"moles": {"value": 17.7, "units": "MILLIMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1-n-dodecylazacycloheptan-2-one"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3 g of 6-(4-aminophenyl)-8,9-dimethoxy-2-methyl-1,2,3,4,4a,10b-hexahydro-benzo[c][1,6]naphthyridine and 6,2 g of valeric acid chloride are heated to the boil under reflux in 70 ml of acetonitrile for 7 hour... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "6-(4-aminophenyl)-8,9-dimethoxy-2-methyl-1,2,3,4,4a,10b-hexahydro-benzo[c][1,6]naphthyridine"}], "amount": {"mass": {"value": 3.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "valeric acid ch... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Paraiodophenol (25 g) was dissolved in DMF (100 ml), followed by the addition of potassium t-butoxide (25 g) and methoxymethyl chloride (13 ml), and the mixture was reacted at 60° C. overnight. The reaction... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "REACTANT"}]}, "m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium t-butoxide"}], "amount": {"mass": {"value": 25.0, "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:
By reacting 3.7 g. (0.0280 mole) of 2,5-dimethoxy-tetrahydrofuran with 5 g. (0.0276 mole) of 2-hydrazino-4,5-dihydro-1H-imidazole hydrobromide according to the process reported in Example 3, and adding at t... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2,5-dimethoxy-tetrahydrofuran"}], "amount": {"moles": {"value": 0.028, "units": "MOLE"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-hydrazino-4,5-dihydro-1H-imidazole hydrobromide"}], ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 16-(3-(4-(diethylamino)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)phenyl)-4,7,10,13-tetraoxahexadecan-1-oic acid (300 mg, 0.37 mmol), 4-(piperazin-1-yl)phenol (7... | {"inputs": {"m1_m2_m3_m5_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "16-(3-(4-(diethylamino)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)phenyl)-4,7,10,13-tetraoxahexadecan-1-oic acid"}], "amount": {"mass": {"value": 300.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTAN... |
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 described in step 1 of Example 1 from 2-(4-hydrazinophenyl)ethanol hydrochloride and 1,1,1-trifluoro-2,4-pentanedione: MS (ESI) m/z 270 [M+H]+, 1H-... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(4-hydrazinophenyl)ethanol hydrochloride"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1,1,1-trifluoro-2,4-pentanedione"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
5-{3-[2-[4′-(Cyclohexylmethyl-amino)-biphenyl-4-ylmethyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-[1,2,5]thiadiazolidin-3-one-1,1-dioxide (7 mg, 0.01 mmol) was reacted with acetaldehyde (2 mg, 0.04 m... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "5-{3-[2-[4\u2032-(Cyclohexylmethyl-amino)-biphenyl-4-ylmethyl]-4-(2,4-dichloro-phenyl)-imidazol-1-yl]-phenyl}-[1,2,5]thiadiazolidin-3-one-1,1-dioxide"}], "amount": {"mass": {"value": 7.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of the compound of Example I, C. (21.7 g., 0.1 mole) and p-n-butylaniline (14.9 g., 0.1 mole) in ethanol (200 ml.) was stirred and refluxed overnight. The reaction solution was concentrated to dry... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "compound"}], "reaction_role": "REACTANT"}]}, "m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "p-n-butylaniline"}], "amount": {"mass": {"value": 14.9, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To potassium carbonate (76 mg) taken in ethanol (2.0 mL), a solution of 2,6-diazaspiro[3.3]heptane (220 mg in 2.0 ml of ethanol) was added at room temperature. The reaction mixture was stirred for 30 minute... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "5-chloro-1-phenyl tetrazole"}], "amount": {"mass": {"value": 0.1, "un... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A hot solution of 2,5-dihydroxybenzoic acid (gentisic acid) (0.582 g, 3.78 mmol) in absolute ethanol (1 mL) was added to a warm solution of (2S)-(4E)-N-methyl-5-(5-methoxy-3-pyridinyl)-4-penten-2-amine (1.0... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1_m4_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "2,5-dihydroxybenzoic acid"}], "amount": {"mass": {"value": 0.58... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared in analogy to the procedure described in Step 23.9 using 4-(4-chlorophenyl)-1-cyclopropyl-5-(4-methoxybenzyl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one (Step 85.5) ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(4-chlorophenyl)-1-cyclopropyl-5-(4-methoxybenzyl)-3-methyl-4,5-dihydropyrrolo[3,4-c]pyrazol-6(1H)-one"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Hexane EtOAc"}], "reaction_role": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
C.hydrochloric acid (1 drop) was added to a stirred solution of 3-hydrazino-5-methyl-6-phenyl-1,2,4-triazine (4.12 g) and propionaldehyde (4 ml) in methanol (15 ml) at room temperature, and the stirring was... | {"inputs": {"m3_m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-hydrazino-5-methyl-6-phenyl-1,2,4-triazine"}], "amount": {"mass": {"value": 4.12, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "propionaldehyde"}], "amount": {"volume": {"value": 4.0, ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 1000 g of sulfuric acid, 175.6 g (0.825 mole) of 4-methoxybenzophenone, 0.5 g of 2,5-di-tert-butyl-p-cresol and 86 g (0.851 mole) of N-methylolacrylamide was reacted for 5 hours at 25° C. and t... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sulfuric acid"}], "amount": {"mass": {"value": 1000.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-methoxybenzophenone"}], "amount": {"mass": {"value": 175.6, "units": "GRAM"}}, "rea... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 1.5 g (13.26 mmol) of 5-fluoro-3-pyridinol in 8 ml of acetic acid is heated to 70° C. and 1.25 ml (14.6 mmol) of 35% hydrogen peroxide are added gradually. The reaction mixture is stirred for ... | {"inputs": {"m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "5-fluoro-3-pyridinol"}], "amount": {"mass": {"value": 1.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "amount": {"volume": {"value": 8.0, "units": "MILLILITER"}}, "reaction_... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
436 mg (0.8 mmol) of tert-butyl (2S)-2-(1-adamantylmethyloxycarbonylamino)-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate were added to a solution of 388 mg (3.2 mmol) of 2-amino-4,5-dihydroimidazole hyd... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl (2S)-2-(1-adamantylmethyloxycarbonylamino)-3-(4-(3-ethoxycarbonylpropyloxy)phenyl)propionate"}], "amount": {"mass": {"value": 436.0, "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:
To a solution of 8.98 g (86.33 mmole) sodium bisulfite in water (27 mL), o-chlorobenzaldehyde 12.4 g (86.33 mmole) was added resulting in a white precipitate. To the precipitate, 15 g (0.107 moles) of 6,7-d... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "NaCN"}], "amount": {"volume": {"value": 15.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium bisulfite"}], "amount": {"mass": {"value": 8.98, "units": "G... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a CHCl3 (1.0 mL) solution of the compound (365 mg) obtained in Example 13-(2), TFA (5.0 mL) was added at 0° C. and the mixture was stirred at room temperature for 2 hours. After concentrating the reactio... | {"inputs": {"m3_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "compound"}], "amount": {"mass": {"value": 365.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "TFA"}], "amount": {"volume": {"value": 5.0, "units": "MILLILITER"}}, "reaction_role": "RE... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 2-amino-4,5-dimethylthiazole and 2-(bromoethyl)tetrahydro-2H-pyran were processed as described in Example 2A to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.13-1.31 (m, 1H), 1.3... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-amino-4,5-dimethylthiazole"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-(bromoethyl)tetrahydro-2H-pyran"}], "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:
To a solution of 1.74 g (7.76 mmol) of 4-(2,2-dimethylpropyl)-4-ethenylbenzene (from Step A) in 10 mL EtOAc and 10 mL H2O was added 8.30 g (38.8 mmol) of NaIO4 and 1 mg (0.0078 mmol) RuO2. The reaction mixt... | {"inputs": {"m1_m4_m6_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(2,2-dimethylpropyl)-4-ethenylbenzene"}], "amount": {"mass": {"value": 1.74, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "NaIO4"}], "amount": {"mass": {"value": 8.3, "units": "GRAM... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
5-(4-Chlorophenylsulfonyl)-6-(3-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine Benzyl 2-(3-fluorophenyl)-4-oxopiperidine-1-carboxylate, prepared as described for compound 67 in Example 3 using ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "hydrazine hydrate"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(4-Chlorophenylsulfonyl)-6-(3-fluorophenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine Benzyl 2-(3-fluorophenyl)-4-ox... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Triethylamine (66.5 g, 0.658 moles) was added to a solution of 4-[(1-Cyclobutyl-4-piperidinyl)oxy]aniline (81 g, 0.329 moles, obtained in preparation 1) in dichloromethane (1 L), at 0° C. under nitrogen atm... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "chloro acetyl chloride"}], "amount": {"mass": {"value": 44.6, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "dichloromethane"}], "amount": {"volume": {"value": 1.0, "units": "LITER"}}, "reactio... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a slurry solution of sodium hydrosulphide (2.80 g, 50 mmol) and magnesium chloride hexahydrate (5.05 g, 25 mmol) in dimethylformamide (50 ml) is added 4-bromo-2-methyl benzonitrile (4.90 g, 50 mmol) in o... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydrosulphide"}], "amount": {"mass": {"value": 2.8, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "magnesium chloride hexahydrate"}], "amount": {"mass": {"value": 5.05, "units": "G... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a microwave vial, 3-(4-bromophenoxy)-2-(4-hydroxyphenyl)benzo[b]thiophen-6-ol (50 mg, 0.121 mmol) was dissolved in DMF (2 ml) and triethyl amine (0.506 ml, 3.63 mmol). To the solution was added the 4-vin... | {"inputs": {"m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "4-vinyl-1-methyl imidazole"}], "amount": {"mass": {"value": 39.2, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Pd(PPh3)2Cl2"}], "amount": {"mass": {"value": 8.49, "units": "MILLIGRAM"}},... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 6-fluoro-2-methylquinolin-7-ol (800 mg, 3.16 mmol) in acetone (5 mL) were added 2-iodopropane (1075 mg, 6.32 mmol) and potassium carbonate (1310 mg, 9.48 mmol). The reaction was stirred at 70° C. in a se... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "6-fluoro-2-methylquinolin-7-ol"}], "amount": {"mass": {"value": 800.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-iodopropane"}], "amount": {"mass": {"value": 1075.0, "units": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Ethyl 4-hydroxybenzoate is reduced to ethyl 4-hydroxycyclohexanecarboxylate according to the procedure described in R. A. Finnegan and P. L. Bachman, Journal of Organic Chemistry, Volume 30, pages 4145-4150... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "isopropanol"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Ethyl 4-hydroxybenzoate"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "et... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Method as described for methyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate (intermediate 25) using (S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine (in... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "intermediate 6"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl 2-chloro-4-morpholino-5H-pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate"}], "reaction_role": "REACTANT"}]}, "m2": {"compon... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A dry RBF set up with stirring bar and reflux condenser was charged with 4-(6-methylpyridin-2-yl)phthalazin-1(2H)-one (780 mg, 3.29 mmol) and POCl3(10.7 ml, 115 mmol). This was stirred under reflux for 18 h... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "4-(6-methylpyridin-2-yl)phthalazin-1(2H)-one"}], "amount": {"mass": {"value": 780.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "POCl3"}], "amount": {"volume": {"value": 10.7, "units": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A suspension of 2-(3-(4-(1H-indazol-5-ylamino)quinazolin-2-yl)phenoxy)acetic acid (70 mg, 0.14 mmol), PyBOP® (40 mg, 0.077 mmol), DIEA (24 μL, 0.14 mmol) in dry CH2Cl2:DMF (2:0.1 mL) was stirred at RT for 1... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-tetrahydrofuran-3-aminium 4-methylbenzenesulfonate"}], "amount": {"mass": {"value": 24.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "(R)-tetrahydrofuran-3-amin... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The process is carried out as in Example 43 above, with compound A 1-[3-(2,4-dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-4-ethoxybutane-1,3-dione and hydrazine hydrate
### OR... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "compound A"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-[3-(2,4-dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-4-ethoxybutane-1,3-dione"}], "reaction_role"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Intermediate 73 (24 g, 0.096 moles) was taken in a RB flask and to this acetic anhydride (230 ml) and sodium acetate (55.2 g, 0.673 moles) were added and the mixture was refluxed for 12 h. After cooling to ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 73"}], "amount": {"mass": {"value": 24.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium acetate"}], "amount": {"mass": {"value": 55.2, "units": "GRAM"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Solutions of 375 ml (325 g, 2.8 moles) of isoamyl nitrite, and of 378 grams (2.0 moles) of crude 4-bromo-2-fluoroaniline in 250 ml benzene are added separately and simultaneously dropwise over about 20 hour... | {"inputs": {"m6_m7": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 1.0, "units": "LITER"}}, "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value": "Skellysolve B hexanes"}], "amount": {"volume": {"value": 1.0, "units": "LITER"}}, "reaction_role": "... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 8 g of N-(3-{[tertbutyl(dimethyl)silyl]oxy}propyl)-N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-3,4-dimethoxybenzenesulfonamide in 80 ml of tetrahydrofuran at 0° C. are added 2.98 g of tetrabutylammonium fl... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "N-(3-{[tertbutyl(dimethyl)silyl]oxy}propyl)-N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-3,4-dimethoxybenzenesulfonamide"}], "amount": {"mass": {"value": 8.0, "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:
Isopropylamine (4.5 ml) and N,N-diisopropylethylamine (13.2 ml) were dissolved into 150 ml dichloromethane. The mixture was added dropwise to a solution of 2,4-dichloro-5-nitro-6-methylaminopyrimidine (11.5... | {"inputs": {"m1_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "Isopropylamine"}], "amount": {"volume": {"value": 4.5, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-diisopropylethylamine"}], "amount": {"volume": {"value": 13.2, "units": "MILLI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of ethyl (3-hydrazinophenyl)acetate (15 g, 65 mmol) and 4,4-dimethyl-3-oxopentanenitrile (12.5 g, 0.1 mol) in EtOH (100 mL) containing conc. HCl (25 mL) was heated at reflux overnight. After remo... | {"inputs": {"m1_m2_m4_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl (3-hydrazinophenyl)acetate"}], "amount": {"mass": {"value": 15.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4,4-dimethyl-3-oxopentanenitrile"}], "amount": {"mass": {"value": 12... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of 1-fluoro-2-methylpropan-2-amine hydrochloride (ABCR) (2 g, 15.7 mmol), anhydrous magnesium sulfate (3.77 g, 31.4 mmol) and potassium carbonate (2.17 g, 15.68 mmol) in dichloromethane (100... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "hexanal"}], "amount": {"volume": {"value": 1.93, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "1-fluoro-2-methylpropan-2-amine hydrochloride"}], "amount": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The same operation as in Example (196c) was performed using tert-butyl trans(±)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-(cyclopropylamino)piperidine-1-carboxylate obtained in Example (213a)... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium carbonate"}], "amount": {"mass": {"value": 82.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl trans(\u00b1)-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In 500 ml of chloroform, 50 g of 1-[4-chloro-6-fluoro-3-hydroxy-2-(2 -methyl-2-propenyl)phenyl]-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione was dissolved, to which 30.0 g of m-chlorope... | {"inputs": {"m4_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-[4-chloro-6-fluoro-3-hydroxy-2-(2 -methyl-2-propenyl)phenyl]-3-methyl-4-trifluoromethyl-1,2,3,6-tetrahydropyrimidine-2,6-dione"}], "amount": {"mass": {"value": 50.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a 1-L flask kept cold in an ice bath, add triphenylphosphine (27.9 g, 106.3 mmol), 4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile (24.12 g, 106.3 mmol). Add DCM slowly with stirring (150 mL... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(6-fluoro-pyridin-3-yl)-ethanol"}], "amount": {"mass": {"value": 10.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "DCM"}], "reaction_role": "SOLVENT"}]}, "m1_m2": {"co... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To benzothiazole (3.46 g, 25.6 mmol) dissolved in dry THF under a nitrogen atmosphere at −78° C. was added butyl lithium (17.1 mL of 1.5M solution, 1 equiv.) dropwise. The reaction mixture was stirred for 1... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "butyl lithium"}], "amount": {"volume": {"value": 17.1, "units": "MILLILI... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Esterification of 2-(6-carboxy-5,5-dimethylhexyl)cyclopentan-1-one with ethanol by the procedure described in Example 3 is productive of the subject compound.
### ORD JSON:
| {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-(6-carboxy-5,5-dimethylhexyl)cyclopentan-1-one"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "REACTANT"}]}}, "conditions": {"conditions_are_dynamic": true}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of cyclohexylmethanol (9 μmol) in DMF were added sequentially solutions of 2-[4-(3-bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-[1,2,4]triazine-6-carboxylic acid ... | {"inputs": {"m1_m4_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "cyclohexylmethanol"}], "amount": {"moles": {"value": 9.0, "units": "MICROMOLE"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-[4-(3-bromo-4-methoxy-phenoxy)-3,5-dimethyl-phenyl]-3,5-dioxo-2,3,4,5-te... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Under cooling (0° C.), sodium ethanolate (2.18 g, 32 mmol) was added to a mixture of 4-fluorophenol ([371-41-5], 3.00 g, 27 mmol), ethyl 4-chlorobutyrate ([3153-36-4], 4.84 g, 32 mmol) and ethanol (15 ml), ... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium ethanolate"}], "amount": {"mass": {"value": 2.18, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4-fluorophenol"}], "amount": {"mass": {"value": 3.0, "units": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
N-[(2-Cyclopropylmethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)acetyl]guanidine is prepared as described in Example 1, starting with 2.9 g of potassium tert-butoxide, 2.5 g of guanidinium chloride and 1.5 g of ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "amount": {"volume": {"value": 20.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "potassium tert-butoxide"}], "amount": {"mass": {"value": 2.9, "units": "G... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 0.323 g (0.13 mmol) of the product of Step C in 10 mL of anhydrous THF was carefully added 0.1 g (2.63 mmol) of lithium aluminum hydride. The reaction mixture was then stirred overnight und... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "sodium hydroxide"}], "reaction_role": "REACTANT"}]}, "m6": {"components": [{"identifiers": [{"type": "NAME", "value": "THF"}], "amount": {"volume": {"value": 10.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of ethyl [2-ethyl-4-(hydroxymethyl)phenoxy]acetate (2.74 g, 11.5 mmol) in chloroform (250 mL) was added manganese dioxide (10 g, 11.5 mmol). The resulting mixture was stirred for 18 h at room ... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl [2-ethyl-4-(hydroxymethyl)phenoxy]acetate"}], "amount": {"mass": {"value": 2.74, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "chloroform"}], "amount": {"volume": {"value": 250.0, "un... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared via {2-[3-cyclopentylmethyl-3-(3-chloro-4-fluoro-phenyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid ethyl ester in a similar manner as described for the synthesis of {2-[3-cyc... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "(2-amino-thiazol-5-ylsulfanyl)acetic acid ethyl ester"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "{2-[3-cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)-ureido]-thiazol-4-yl}-acetic acid... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3-Ethoxy-2,2-dimethyl-3-oxopropanoic acid (100 mg, 0.624 mmole) was added to a stirring suspension of 2.5 equivalents of PS-DCC from Argonaut and 3 equivalents of dimethylaminopyridine in DCM. To this was a... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methanesulfonamide"}], "amount": {"mass": {"value": 41.6, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "3-Ethoxy-2,2-dimethyl-3-oxopropanoic acid"}], "amount... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of commercially available t-butyl magnesium chloride in THF (1.0 mol) is added at 38°-40° C. a solution of 4-trifluoromethoxybenzaldehyde (56 g, 0.4 mol) in THF (50 ml) under nitrogen atmosphe... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Ether"}], "reaction_role": "REACTANT"}]}, "m1_m6_m2_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "t-butyl magnesium chloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "4-trifluoromethoxybe... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared from (2-amino-4-chloro-5-pyrrolidin-1-yl-phenyl)-carbamic acid tert.-butyl ester (Example J10) and (RS)-3-oxo-3-{3-[5-(tetrahydro-pyran-2-yloxymethyl)-[1,2,3]triazol-1-yl]-ph... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "(2-amino-4-chloro-5-pyrrolidin-1-yl-phenyl)-carbamic acid tert.-butyl ester"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "(RS)-3-oxo-3-{3-[5-(tetrahydro-pyran-2-yloxymethyl)-[1,2,3]triaz... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The title compound was prepared from commercially available 4,5-dichloro-1,2-phenylendiamine (133 mg, 0.75 mmol) and 3-[3-(2-isopropyl-pyridin-4-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester (Example K3... | {"inputs": {"m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "4,5-dichloro-1,2-phenylendiamine"}], "amount": {"mass": {"value": 133.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-[3-(2-isopropyl-pyridin-4-yl)-phenyl]-3-oxo-propionic acid tert... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a suspension of the quinoline-3-carboxylic acid (480 mg, 2.77 mmol) and N,O-dimethyhydroxylamine hydrochloride (405 mg, 4.15 mmol), in dichloromethane (10 mL) was added triethyl amine (1.93 mL, 13.8 mmol... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "bromo(trispyrrolidin-1yl)phosphonium hexafluorophosphate"}], "amount": {"mass": {"value": 1.55, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m5_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "triethyl amine"}], "amount... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 4-chloro-2-hydroxy-6-methyl-3-nitropyridine (188 mg, 1.0 mmol) in 2 mL of EtOH and 0.2 mL (1.4 mmol) of Et3N was added 0.11 mL (1.0 mmol) of PhSH. Precipitation occurred immediately and the... | {"inputs": {"m1_m4_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4-chloro-2-hydroxy-6-methyl-3-nitropyridine"}], "amount": {"mass": {"value": 188.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "Et3N"}], "amount": {"volume": {"value": 0.2, "units... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a solvent including an ethyl alcohol (2 mL) and water (2 mL), a mixture including syringaldehyde (100 mg, 0.55 mmol), cysteamine.HCl (93.2 mg, 0.82 mmol), and sodium acetate (72 mg, 0.88 mmol) was stirre... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl alcohol"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "syringaldehyde"}], "amount": {"mass": {"value": 100.0, "units": "M... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 1-(2-bromoethyl)-4-nitrobenzene (6.4 g), 1,2,3,4-tetrahydro-6-methoxyisoquinoline (4.6 g; Daniel J. Sall and Gary L. Grunewald, J. Med. Chem. 1987, 30, 2208-2216) and potassium carbonate (9.7 g... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(2-bromoethyl)-4-nitrobenzene"}], "amount": {"mass": {"value": 6.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "1,2,3,4-tetrahydro-6-methoxyisoquinoline"}], "amount": {"mass": {"valu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 0.47 g (1.69 mmol) (S)-7-amino-5-cyclopropylmethyl-5H,7H-dibenzo[b,d]azepin-6-one in 15 ml tetrahydrofurane was treated at 0° C. with 0.17 g (1.86 mmol) L-lactic acid, 0.26 g (1.69 mmol) 1-hyd... | {"inputs": {"m1_m6_m2_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "(S)-7-amino-5-cyclopropylmethyl-5H,7H-dibenzo[b,d]azepin-6-one"}], "amount": {"mass": {"value": 0.47, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "L-lactic acid"}], "amount": {"ma... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 8-nitroquinoline (1.035 g, 5,94 mmol) and platinum oxide (35 mg, 0.15 mmol, 2.5 mol %) in glacial acetic acid was hydrogenated (20 psi) on a Parr Shaker at room temperature for 20 hours. The mi... | {"inputs": {"m1_m7_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "8-nitroquinoline"}], "amount": {"mass": {"value": 1.035, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acetic acid"}], "reaction_role": "SOLVENT"}, {"identifiers": [{"type": "NAME", "value"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of tert-butyl [(2R,3S,5R)-2-(2,5-difluorophenyl)-5-(4,6-dihydropyrrolo[3,4-c]pyrazol-5(1H)-yl)-1-methyl-6-oxopiperidin-3-yl]carbamate (70 mg, 0.161 mmol) in dichloromethane (4 mL) at room temp... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "TFA CH2Cl2"}], "reaction_role": "REACTANT"}]}, "m1_m5_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "tert-butyl [(2R,3S,5R)-2-(2,5-difluorophenyl)-5-(4,6-dihydropyrrolo[3,4-c]pyrazol-5(1H)-yl)-1-methyl-6-oxopiperidin-3-yl... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
The intermediate from Step 4 (36 mg, 0.06 mmol) was dissolved in MeOH (2 mL). To the solution was added 10% Pd/C (20 mg) and 3 N HCl in MeOH (0.1 mL). The mixture stirred under H2 (1 atm) at room temperatur... | {"inputs": {"m1_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "intermediate"}], "amount": {"mass": {"value": 36.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "MeOH"}], "amount": {"volume": {"value": 2.0, "units": "MILLILITER"}}, "reaction_role": "S... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Methanesulfonyl chloride (0.019 mL, 0.245 mmole) was added dropwise to a solution of 8-{3-[(6-aminohexyl)oxy]benzyl}-4-(cyclohexylamino)-1-(3-fluorophenyl)-1,3,8-triazaspiro[4.5]dec-3-en-2-one (0.116 mg, 0.... | {"inputs": {"m1_m2_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "Methanesulfonyl chloride"}], "amount": {"volume": {"value": 0.019, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "8-{3-[(6-aminohexyl)oxy]benzyl}-4-(cyclohexylamino)-1-(3-fluorophenyl)... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Sodium azide (158 mg, 2.43 mmol) was added to a solution of methyl 2-(bromomethyl)-5-chlorobenzoate (518 mg, 1.97 mmol) in 3 mL of DMF at room temperature. After stirring overnight, reaction mixture was que... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "Sodium azide"}], "amount": {"mass": {"value": 158.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methyl 2-(bromomethyl)-5-chlorobenzoate"}], "amount": {"mass": {"value": 518.0, "unit... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of trifluoromethanesulfonic anhydride (30 mL, 170 mmol) in anhydrous dichloromethane (50 mL) was added drop-wise a solution of 2-hydroxypropanoic acid ethyl ester (20 g, 170 mmol) and ... | {"inputs": {"m1_m4_m2_m3_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "trifluoromethanesulfonic anhydride"}], "amount": {"volume": {"value": 30.0, "units": "MILLILITER"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "2-hydroxypropanoic acid ethyl ester"}], "amount": {"mas... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Compound 220b was synthesized from 2-methyl-3-methoxyaniline hydrochloride 215b and malonic acid as a white powder in 43% yield, following the procedure as described for compound 220d. 1H NMR (CDCl3, 376 MH... | {"inputs": {"m0_m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "2-methyl-3-methoxyaniline hydrochloride"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "malonic acid"}], "reaction_role": "REACTANT"}]}, "m3": {"components": [{"identifiers": [{"type": "NAME", "value": "com... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Aniline, (102.3 g, 1.1 mole) was added to 50 ml of dioxane, 108 g of 1,2-epoxy butane and 1 g of potassium fluoride in 25 ml of water. The mixture heated to reflux for 30 hours. The mixture was poured into ... | {"inputs": {"m6": {"components": [{"identifiers": [{"type": "NAME", "value": "methylene chloride"}], "amount": {"volume": {"value": 200.0, "units": "MILLILITER"}}, "reaction_role": "SOLVENT"}]}, "m7": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3_m4_m5": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 5-amino-3-(2-propynyl)-3H-benz-oxazol-2-one (0.50 g), 3,4,5,6-tetrahydrophthalic anhydride (0.53 g) and acetic acid (5 ml) was heated at 100 to 110° C. under reflux for 3 hours. After being all... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "water"}], "reaction_role": "SOLVENT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "5-amino-3-(2-propynyl)-3H-benz-oxazol-2-one"}], "amount": {"mass": {"value": 0.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Following the general method as outlined in Intermediate 19, starting from tert-butyl(4-chloro-2-ethynylphenoxy)acetate (Intermediate 3) and 3-bromo-4-fluorobenzonitrile (ABCR), the title compound was obtai... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-bromo-4-fluorobenzonitrile"}], "reaction_role": "REACTANT"}]}, "m1": {"components": [{"identifiers": [{"type": "NAME", "value": "Intermediate 19"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "va... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To 7-methoxy-4-(phenylthio)quinoline (1.38 g, 5.16 mmol) in CH2Cl2(50 mL) at −78° C. was added m-CPBA (77%) (1.25 g, 7.23 mmol) portionwise. The mixture was allowed to slowly warm to RT (3 hrs). The reactio... | {"inputs": {"m1_m5_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "7-methoxy-4-(phenylthio)quinoline"}], "amount": {"mass": {"value": 1.38, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "m-CPBA"}], "amount": {"mass": {"value": 1.25, "units": "GRAM"}}, "reac... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Donnelly and co-workers (Donnelly, D. M. X.; Fitzpatrick, B. M.; Ryan, S. M.; Finet, J.-P. J. Chem. Soc., Perkin Trans. I 1994, 1794-1801) synthesized the biflavonoids (46) and (47) via arylation of a 3-phe... | {"inputs": {"m0_m1_m6_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "acetone"}], "reaction_role": "SOLVENT"}]}, "m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3,8-biflavanone"}], "reaction_role"... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
Osmium (VIII) oxide (2.5% wt in tert-butanol, 0.1 mL) was added to a solution of 3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyrazolo[4,3-c]pyridin-2-yl]-5-vinylbenzonitrile (42 mg, 0.1 mmol) in ace... | {"inputs": {"m2": {"components": [{"identifiers": [{"type": "NAME", "value": "Sodium periodate"}], "amount": {"mass": {"value": 47.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}]}, "m5_m1_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "3-chloro-2-[7-fluoro-4-(6-methylpyrimidin-4-ylamino)pyr... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of ethyl 3-amino-4-chloro-2-(methylsulphenylmethyl)benzoate (50 g) in ethanol was added to a stirred suspension of Raney Nickel (300 g) in ethanol. After stirring overnight at room temperature, a... | {"inputs": {"m1_m3_m4_m5": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 3-amino-4-chloro-2-(methylsulphenylmethyl)benzoate"}], "amount": {"mass": {"value": 50.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "ethanol"}], "reaction_role": "SOLVENT"}, {"i... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
According to the general method of Example 7, 1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine and chloroformic acid 1-naphthyl ester were combined to provide 1-naphthyl N-[4-(4-amino-1H-imidazo[4,5-c]qui... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-(4-aminobutyl)-1H-imidazo[4,5-c]quinolin-4-amine"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "chloroformic acid 1-naphthyl ester"}], "reaction_role": "REACTANT"}]}}, "conditions": {"c... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of acetic acid (R)-2-(5-amino-1-oxo-1H-isoquinolin-2-yl)-propyl ester (20 g, 0.07 mol) in carbon tetrachloride (400 mL, 4 mol) at 60° C. was added a solution of N-chlorosuccinimide (11 g, 0.08... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "acetic acid (R)-2-(5-amino-1-oxo-1H-isoquinolin-2-yl)-propyl ester"}], "amount": {"mass": {"value": 20.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "carbon tetrachloride"}], "amount":... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A mixture of 12.5 g of 1,3,4,9b-Tetrahydro-5-methyl-2H-indeno[1,2-c]pyridine and 10 g acrylic acid ethyl ester are heated in 100 ml of ethanol for 3 hours at 80° C and then evaporated to dryness. The title ... | {"inputs": {"m1_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1,3,4,9b-Tetrahydro-5-methyl-2H-indeno[1,2-c]pyridine"}], "amount": {"mass": {"value": 12.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "acrylic acid ethyl ester"}], "amount": {"mass": {"val... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a solution of 1-[4-(benzenesulfonylamino)methyl-1,3-thiazol-2-yl]-3-methanesulfonyloxyazetidine (1.16 g, 2.98 mmol) (obtained as described in Reference Example 65(3)) in dimethylformamide (35 ml) was add... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "1-[4-(benzenesulfonylamino)methyl-1,3-thiazol-2-yl]-3-methanesulfonyloxyazetidine"}], "amount": {"mass": {"value": 1.16, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "pota... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
To a stirred solution of 2,4-diethyl-9H-thioxanthen-9-one (20 g, 74.5 mmol) in methanol (400 ml) cooled in an ice bath was added sodium borohydride (8 g, 0.2 mole) portionwise. After 1 hour at room temperat... | {"inputs": {"m1_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "2,4-diethyl-9H-thioxanthen-9-one"}], "amount": {"mass": {"value": 20.0, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "methanol"}], "amount": {"volume": {"value": 400.0, "units": "MILLILITER"}}... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
4,4-Diethyl-3,4-dihydro-2-dimethylaminomethylene-7-methoxy-1(2H) naphthalenone was prepared from 4,4-diethyl-3,4-dihydro-7-methoxy-1(2H)naphthalenone (1.50 g, 6.5 mmol) and N,N-dimethylformamide diethyl ace... | {"inputs": {"m0_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "4,4-diethyl-3,4-dihydro-7-methoxy-1(2H)naphthalenone"}], "amount": {"mass": {"value": 1.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "N,N-dimethylformamide diethyl acetal"}], "amount": {... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In the manner described in example 3, 2-bromophenylacetic acid is condensed with 3,5-dinitroaniline to yield 2-[(3,5-dinitrophenyl)amino]phenylacetic acid.
### ORD JSON:
| {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "2-bromophenylacetic acid"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "3,5-dinitroaniline"}], "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:
A solution of Kryptofix® 2.2.2 (23.4 mg, 0.062 mmol) in acetonitrile (2 mL) was added to a solution of KF (7.3 mg, 0.125 mmol) in water (0.5 mL). The solvents were evaporated at 120° C. and the residue was ... | {"inputs": {"m2_m7_m3_m8": {"components": [{"identifiers": [{"type": "NAME", "value": "2.2.2"}], "amount": {"mass": {"value": 23.4, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "KF"}], "amount": {"mass": {"value": 7.3, "units": "MILLIGRAM"}}, "reaction_role": "REACTAN... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
A solution of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (4.3 g, 17.7 mmol), [bis(trifluoroacetoxy)iodolbenzene (15.6 g, 36.2 mmol), H2O (18 ml), CF3CO2H (2.8 ml) and CH3 CN (90 ml) was refluxed for 3 ... | {"inputs": {"m1_m3_m2": {"components": [{"identifiers": [{"type": "NAME", "value": "1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone"}], "amount": {"mass": {"value": 4.3, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "CF3CO2H"}], "amount": {"volume": {"value": 2.8, "units": ... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
5-(N,N-Dibenzylglycyl)salicylamide (37.4 g) was heated at reflux for 2 hours with methyl iodide (10 ml) and anhydrous potassium carbonate (20 g) in ethyl methyl ketone (350 ml). The inorganic salts were fil... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "5-(N,N-Dibenzylglycyl)salicylamide"}], "amount": {"mass": {"value": 37.4, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "methyl iodide"}], "amount": {"volume": {"valu... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
D-alanine methyl ester hydrochloride (420 mg) and 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indole-3-carbaldehyde (D71) (382 mg) was added to a solution of NaOH (120 mg) in metha... | {"inputs": {"m1_m2_m3_m4": {"components": [{"identifiers": [{"type": "NAME", "value": "D-alanine methyl ester hydrochloride"}], "amount": {"mass": {"value": 420.0, "units": "MILLIGRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiaz... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
3,4-Dimethoxy-N-methyl-5-nitro-benzimidoyl chloride (0.28 g, 1.08 mmol) was added to a stirred solution of 3-(2H-tetrazol-5-yl)-2-(trifluoromethyl)pyridine (0.215 g, 1 mmol) in dry pyridine (3 mL), preheate... | {"inputs": {"m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3,4-Dimethoxy-N-methyl-5-nitro-benzimidoyl chloride"}], "amount": {"mass": {"value": 0.28, "units": "GRAM"}}, "reaction_role": "REACTANT"}, {"identifiers": [{"type": "NAME", "value": "3-(2H-tetrazol-5-yl)-2-(trifluoromethyl)pyridine"}],... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
When the above product is allowed to stand at room temperature in ethyl acetate for 2 days, a transesterification reaction occurs, the ethyl 1,3-bis(2',6'-dimethylphenyl)-2-imino-imidazolidine-4-acetate, me... | {"inputs": {"m1": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl 1,3-bis(2',6'-dimethylphenyl)-2-imino-imidazolidine-4-acetate"}], "reaction_role": "REACTANT"}]}, "m2": {"components": [{"identifiers": [{"type": "NAME", "value": "ethyl acetate"}], "reaction_role": "SOLVENT"}]}}, "conditions": {"condit... |
Below is a description of an organic reaction. Extract information from it to an ORD JSON record.
### Procedure:
In a 100-ml flask, 4.9 g (50 mmol) of 3-aminopyrazine, 4.5 g (59 mmol) of carbon disulfide and 50 ml of ethyl acetate were placed, and 6.5 g (64 mmol) of triethylamine was added dropwise with stirring over ... | {"inputs": {"m4": {"components": [{"identifiers": [{"type": "NAME", "value": "triethylamine"}], "amount": {"mass": {"value": 6.5, "units": "GRAM"}}, "reaction_role": "REACTANT"}]}, "m1_m2_m3": {"components": [{"identifiers": [{"type": "NAME", "value": "3-aminopyrazine"}], "amount": {"mass": {"value": 4.9, "units": "GRA... |
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