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Here is a chemical reaction formula: Reactants are:m3_m1_m2:NCCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC;m3_m1_m2:C1(=CC=CC=C1)OCC1CO1, Reagents are:m3_m1_m2:CO, and Products are 0:OC(CNCCCCOC1=C(C=C(C=C1)S(=O)(=O)C)C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)COC1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 44 ml of methanol were dissolved 2.57 g of dimethyl 4-[2-(4-aminobutoxy)-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (obtained in Reference Example 2) and 0.83 g of glycidyl phenyl ether, and the solution formed was allowed to react at room temperature for 43 hours and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the product was eluted with chloroform-methanol (95:5 v/v). Crude crystals were recrystallized from ethanol-ether to give 1.05 g of dimethyl 4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-methylsulfonylphenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. |
Here is a chemical reaction formula: Reactants are:m3_m1_m2:NCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC;m3_m1_m2:COC1=CC=C(C=C1)OCC1CO1, Reagents are:m3_m1_m2:CO, and Products are 0:OC(CNCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC)COC1=CC=C(C=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 200 ml of methanol were dissolved 2 g of dimethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate and 0.84 g of glycidyl 4-methoxyphenyl ether, and the solution was refluxed under heating for 3 hours. The solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography, and the product was eluted with chloroform-methanol (95:5 v/v). Crude crystals were recrystallized from a mixture of methanol and ethyl ether to give 0.85 g of dimethyl 4-[2-[4-[2-hydroxy-3-(p-methoxyphenoxy)propylamino]butoxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. |
Here is a chemical reaction formula: Reactants are:m3_m1_m2:NCCCCOC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OCC)C)CC)C(=O)OCC;m3_m1_m2:C1(=CC=CC=C1)OCC1CO1, Reagents are:m3_m1_m2:CO, and Products are 0:C(C)C=1NC(=C(C(C1C(=O)OCC)C1=C(C=CC(=C1)[N+](=O)[O-])OCCCCNCC(COC1=CC=CC=C1)O)C(=O)OCC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In 46 ml of methanol were dissolved 4.62 g of diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate and 1.46 g of glycidyl phenyl ether, and the solution formed was refluxed under heating for 15 hours. After cooling the reaction solution, the solution was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the product was eluted with chloroform-methanol (95:5 v/v). Crude crystals were recrystallized from ethanol to give 1.22 g of diethyl 2-ethyl-4-[2-[4-(2-hydroxy-3-phenoxypropylamino)butoxy]-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:[N+](=O)([O-])C1=CC=C(C(C=O)=C1)O;m1_m2_m3_m5:ClC\C=C\CCl;m1_m2_m3_m5:C([O-])([O-])=O.[K+].[K+];m4:O, Reagents are:m1_m2_m3_m5:CN(C=O)C, and Products are 0:ClC/C=C/COC1=C(C=O)C=C(C=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 8 g of 5-nitrosalicylaldehyde, 30.8 g of trans-1,4-dichloro-2-butene and 13.2 g of potassium carbonate in 35 ml of dimethylformamide was stirred at room temperature for 19 hours, and further stirred at 80°-87° C. (outside temperature) for 2 hours. The mixture was allowed to cool, poured into 80 ml of water, and extracted with chloroform. The extract (organic layer separated) was concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel. The product was eluted with benzene to give 5.3 g of 2-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehyde. (mp. 65°-66° C.). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:ClC/C=C/COC1=C(C=O)C=C(C=C1)[N+](=O)[O-];m1_m2_m3_m4:C(CC(=O)C)(=O)OC;m1_m2_m3_m4:N\C(=C/C(=O)OC)\C, Reagents are:m1_m2_m3_m4:C(C)(C)O, and Products are 0:ClC/C=C/COC1=C(C=C(C=C1)[N+](=O)[O-])C1C(=C(NC(=C1C(=O)OC)C)C)C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 5.2 g of 2-[(E)-4-chloro-2-butenyloxy]-5-nitrobenzaldehyde, 2.4 g of methyl acetoacetate and 2.3 g of methyl 3-aminocrotonate was dissolved in 30 ml of iso-propanol, and the solution obtained was refluxed for 3.5 hours under heating. After cooling, the precipitated crystals were collected by filtration to give 4.4 g of dimethyl 4-[2-[(E)-4-chloro-2-butenyloxy]-5-nitrophenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate. (mp. 206°-207° C.). The product obtained was used directly for the next process without purification. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC=1N=C(NC(C1C(=O)OC)C1=CC(=CC=C1)[N+](=O)[O-])C1=CC=CC=C1, Reagents are:m1_m2_m3:C(Cl)(Cl)Cl;m1_m2_m3:[O-2].[O-2].[Mn+4], and Products are 0:CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of methyl 4-methyl-2-phenyl-6-(3-nitrophenyl)-1,6-dihydro-5-pyrimidinecarboxylate (475 g) in chloroform (5 l) was added activated manganese dioxide (1.9 kg) and the mixture was refluxed for two hours with stirring vigorously. After allowing to cool to room temperature, manganese dioxide was filtered off. The filtrate was evaporated in vacuo and the residual precipitate was recrystallized from diisopropyl ether (500 ml). The crystal was filtered off, washed with diisopropyl ether and dried in vacuo to give methyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (320 g). |
Here is a chemical reaction formula: Reactants are:m4:C(C)OCC;m1_m2_m3_m6_m5:[N+](=O)([O-])C=1C=C(C=O)C=CC1;m1_m2_m3_m6_m5:C(C)(=O)CC(C)=O;m1_m2_m3_m6_m5:C(C)(=O)O, Reagents are:m1_m2_m3_m6_m5:C1=CC=CC=C1;m1_m2_m3_m6_m5:N1CCCCC1, and Products are 0:C(C)(=O)C(C(=O)C)=CC1=CC(=CC=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 3-nitrobenzaldehyde (20 g), acetylacetone (13.25 g), acetic acid (1.58 g), and piperidine (0.45 g) in benzene (20 ml) was refluxed for 1 hour under azeotropic dehydration. To the reaction mixture was added diethyl ether (100 ml). The mixture was washed with water (50 ml) and a saturated aqueous solution of sodium chloride (50 ml) successively, dried over magnesium sulfate, and evaporated in vacuo. The residual substance was recrystallized from ether to afford 1-acetyl-1-(3-nitrobenzyliden)acetone(16.5 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:C(C)(=O)C(C(=O)C)=CC1=CC(=CC=C1)[N+](=O)[O-];m1_m2_m3_m5:Cl.C(C1=CC=CC=C1)(=N)N;m1_m2_m3_m5:C(C)N(CC)CC;m4:C(C)(=O)OCC, Reagents are:m1_m2_m3_m5:C(CCC)O, and Products are 0:C(C)(=O)C1=C(N=C(NC1C1=CC(=CC=C1)[N+](=O)[O-])C1=CC=CC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1-acetyl-1-(3-nitrobenzyliden)acetone (10 g), benzamidine hydrochloride (8.06 g) and triethylamine (8.4 ml) in n-butanol (100 ml) was refluxed for 2 hours. The reaction mixture was added ethyl acetate (100 ml), washed with water (100 ml) and 5% hydrochloric acid (100 ml) successively. The solvent was evaporated and the residue was stirred with ethyl acetate (100 ml) for 1 hour. The crystals were collected by filtration, added a mixture of chloroform (100 ml) and water (100 ml) and adjusted to pH 8.5 by saturated potassium carbonate. The organic layer was evaporated in vacuo to give 5-acetyl-4-methyl-6-(3-nitrophenyl)-2-phenyl-1,6-dihydropyrimidine (4.46 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)(=O)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-];m1_m2_m3:[BH4-].[Na+], Reagents are:m1_m2_m3:CO, and Products are 0:OC(C)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5-acetyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (3 g) and sodium borohydride (0.34 g) in methanol (110 ml) was stirred at room temperature for 4 hours. The reaction mixture was evaporated in vacuo and the residue was poured into a mixture of ethyl acetate and water. The separated organic layer was dried over magnesium sulfate and evaporated in vacuo. The crystalline residue was recrystallized from a mixture of n-hexane and diethyl ether to give a 5-(1-hydroxyethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (2.3 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:COC=1C=C(C(=O)CC(=O)OCC)C=CC1OC;m1_m2_m3:COC(N(C)C)OC, Reagents are:m1_m2_m3:O1CCCC1, and Products are 0:COC=1C=C(C(=O)C(C(=O)OCC)=CN(C)C)C=CC1OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of ethyl 2-(3,4-dimethoxybenzoyl)-acetate (25.2 g) and N,N-dimethylformamide dimethyl acetal (17.9 g) in tetrahydrofuran (100 ml) was refluxed for 18 hours under stirring. The reaction mixture was evaporated in vacuo to give ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate (31.09) as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:COC=1C=C(C(=O)C(C(=O)OCC)=CN(C)C)C=CC1OC;m1_m2_m3_m4:Cl.C(C)(=N)N;m1_m2_m3_m4:C(C)N(CC)CC, Reagents are:m1_m2_m3_m4:C(C)O, and Products are 0:CC1=NC=C(C(=N1)C1=CC(=C(C=C1)OC)OC)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of ethyl 2-(3,4-dimethoxybenzoyl)-2-(dimethylaminomethylene)acetate (31 g), acetoamidine hydrochloride (13.3 g) and triethylamine (16.2 g) in ethanol (200 ml) was refluxed for 10 hours under stirring. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of ethyl acetate and water. The separatedorganic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was crystallized from ethyl ether to give ethyl 2-methyl-4-(3,4-dimethoxyphenyl)-5-pyrimidinecarboxylate (14 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:CN1CCN(CC1)C(=O)C(=CC1=CC(=CC=C1)[N+](=O)[O-])C(C)=O;m1_m2_m3_m4:Cl.C(C1=CC=CC=C1)(=N)N;m1_m2_m3_m4:C(C)N(CC)CC, Reagents are:m1_m2_m3_m4:C(CCC)O, and Products are 0:CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)N1CCN(CC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-(4-methylpiperazin-1-ylcarbonyl)-1-(3-nitrophenyl)-1-buten-3-one (20 g), benzamidine hydrochloride (9.9 g) and triethylamine (11.4 ml) in n-butanol (200 ml) was refluxed for 2 hours. After evaporating the solvent, the residue was dissolved in a suspension of water (200 ml) and chloroform (200 ml). The separated organic layer was washed with saturated aqueous sodium chloride and dried over magnesium sulfate. To this solution was added activated manganese dioxide (120 g) and the mixture was refluxed for 1 hour with stirring vigorously. After cooling to a room temperature, manganese dioxide was filtered off. The filtrate was evaporated in vacuo, and the residue was subjected to column chromatography on alumina (200 g) eluting with chloroform. The fractions containing the object compound were combined and concentrated under reduced pressure. The crystals were recrystallized from diethyl ether to give 6-methyl-5-(4-methylpiperazin-1-ylcarbonyl)-4-(3-nitrophenyl)-2-phenylpyrimidine. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:OCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-], Reagents are:m1_m2_m3:C(C)(=O)OCC;m1_m2_m3:[O-2].[O-2].[Mn+4], and Products are 0:C(=O)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 5-hydroxymethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.3 g) in ethyl acetate (10 ml) was added activated manganese dioxide (2.4 g) and the mixture was refluxed for 2 hours under stirring vigorously. After allowing to stand to room temperature, manganese dioxide was filtered off. The filtrate was evaporated in vacuo, and the residual precipitate was recrystallized from diethyl ether to give 5-formyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.15 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:BrCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-];m1_m2_m3:CN1CCNCC1, Reagents are:m1_m2_m3:C(C)(C)O, and Products are 0:CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1CCN(CC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5-bromomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.5 g), N-methylpiperazine (1.17 g) in isopropyl alcohol (15 ml) was refluxed for 6 hours. After evaporating the solvent, the residue was dissolved in chloroform, washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The filtrate was evaporated under reduced pressure, and the residue was subjected to column chromatography on alumina (100 g) eluting with chloroform. The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was recrystallized from diethyl ether to give 6-methyl-5-(4-methylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine. (0.30 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:BrC(C)C=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-];m1_m2_m3:CN1CCNCC1, Reagents are:m1_m2_m3:C(C)(C)O, and Products are 0:CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(C)N1CCN(CC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5-(1-bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.5 g) and N-methylpiperazine (1.13 g) in isopropylalcohol (15 ml) was refluxed for 1.5 hours. The reaction mixture was evaporated in vacuo. The residue was chromatographed on allumina eluting with a mixture of ethyl acetate and n-hexane (1:20). The fractions containing the desired product were combined and concentrated in vacuo. The residue was crystallized from a mixture of n-hexane and diethyl ether to give 6-methyl-5-[1-(4-methylpiperazin-1-yl)ethyl]-4-(3-nitrophenyl)-2-phenylpyrimidine (0.51 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:[S-]C#N.[NH4+];m1_m2_m5:C(C1=CC=CC=C1)(=O)Cl;m3_m6:NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-];m4_m7:C(Cl)(Cl)Cl, Reagents are:m1_m2_m5:CC(=O)C;m3_m6:CC(=O)C;m4_m7:O, and Products are 0:C(C1=CC=CC=C1)(=O)NC(NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])=S, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of ammonium thiocyanate (0.25 g) and benzoyl chloride (0.41 g) in acetone (20 ml) was refluxed for 2 hours, and 5-aminomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.9 g) in acetone (5 ml) was added thereto. After refluxing for 2 hours, the reaction mixture was poured into a mixture of chloroform (100 ml) and water (50 ml). The organic layer was separated, washed with saturated aqueous sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the resulting crystal was recrystallized from diisopropyl ether to give 5-(3-benzoylthioureidomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.1 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C1=CC=CC=C1)(=O)NC(NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])=S;m1_m2_m3_m4:[OH-].[Na+], Reagents are:m1_m2_m3_m4:CO;m1_m2_m3_m4:O, and Products are 0:CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CNC(=S)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5-(3-benzoylthioureidomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.0 g) and sodium hydroxide (0.089 g) in methanol (20 ml) and water (10 ml) was stirred for 1 hour at a room temperature. After evaporating the solvent, water (20 ml) was added thereto and stirred for 30 minutes. The resulting precipitates were collected by filtration, washed with water and dried over phosphorous pentoxide to give 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-thioureidomethylpyrimidine (0.75 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CNC(=S)N;m1_m2_m3:CI;m1_m2_m3:CN(C=O)C, Reagents are:, and Products are 0:N1=C(NCC1)NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-thioureidomethylpyrimidine (0.7 g) and methyl iodide (0.31 g) in N,N-dimethylformamide (20 ml) was stirred for 7 hours at a room temperature. After evaporating the solvent in vacuo, the residual product was dissolved in ethanol (14 ml). Ethylenediamine (0.33 g) was added thereto and refluxed for 2 hours. After cooling, the reaction mixture was poured into a mixture of chloroform (50 ml) and water (100 ml), and adjusted pH to 11.0 with 10% aqueous potassium carbonate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over magnesium sulfate, evaporated in vacuo. The residual product was subjected to column chromatography on alumina eluting with a mixture of chloroform and methanol (50:1). The fractions containing the object compound were combined and concentrated in vacuo. The residue was recrystallized from ethanol to give 5-(1-imidazolin-2-ylaminomethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.06 g). |
Here is a chemical reaction formula: Reactants are:m1_m3:BrCC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC;m2:CN1CCNCC1, Reagents are:m1_m3:C(C)(C)O, and Products are 0:CN1CCN(CC1)CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of methyl 6-bromomethyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (1.5 g) in isopropyl alcohol (15 ml) was added N-methylpiperazine (0.88 g) at 70° C. The reaction mixture was stirred for 10 minutes at the same temperature. After evaporating the solvent, the residue was dissolved in a mixture of chloroform (50 ml) and water (50 ml). The organic layer was separated, dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to column chromatography on alumina (100 g) eluting with chloroform. The fractions containing the object compound were combined and concentrated under reduced pressure. The residual crystal was recrystallized from a mixture of diethyl ether and ethanol to give methyl 6-(4-methylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (0.37 g). |
Here is a chemical reaction formula: Reactants are:m3:O1C(=CC=C1)C(=O)Cl;m1_m2_m4:Cl.Cl.CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1CCNCC1;m1_m2_m4:ClCCl, Reagents are:m1_m2_m4:C(C)N(CC)CC, and Products are 0:CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1CCN(CC1)C(=O)C=1OC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 6-methyl-5-(1-piperazinylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine dihydrochloride (1 g), dichloromethane (10 ml) and triethylamine (0.48 g), was added 2-furoyl chloride (0.31 g) at 5° C. under ice cooling. After stirring for 1 hour at the same temperature, the reaction mixture was concentrated under reduced pressure. The residue was suspended in water and adjusted to pH=9 with aqueous saturated sodium hydrogen carbonate. The precipitate was collected by filtration, washed with water and dried in vacuo to give 6-methyl-5-[4-(2-furoyl)piperazin-1-ylmethyl]-4-(3-nitrophenyl)-2-phenylpyrimidine (1.02 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1C(C=2C(C1=O)=CC=CC2)=O;m1_m2_m3:O.NN, Reagents are:m1_m2_m3:C(C)O, and Products are 0:NCC=1C(=NC(=NC1C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 6-methyl-4-(3-nitrophenyl)-5-phthalimidomethyl-2-phenylpyrimidine (6.9 g) and hydrazine monohydrate (0.8 g) in ethanol (140 ml) was refluxed for 6 hours. After filtering off the insolubles, the filtrate was poured into a suspension of chloroform (200 ml) and water (300 ml) under stirring. The organic layer was separated, washed with aqueous sodium chloride and dried over magnesium sulfate. The solvent was evaporated in vacuo and the resulting crystals were recrystallized from ethanol to give 5-aminomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.12 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:C(C)(=O)C=1C(=NC(=NC1CCN(C)C)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-];m1_m2_m5:[BH4-].[Na+];m3_m4:O;m3_m4:C(Cl)(Cl)Cl, Reagents are:m1_m2_m5:CO, and Products are 0:CN(CCC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])C(C)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5-acetyl-6-(2-dimethylaminoethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine (1 g) and sodium borohydride (0.1 g) in methanol (40 ml) was stirred for 1 hour. The reaction mixture was poured into a mixture of water and chloroform and adjusted the pH to 9. The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of chloroform and methanol (20:1). The fractions containing the desired product were combined and concentrated in vacuo. The residue was recrystallized from diethyl ether to afford 6-(2-dimethylaminoethyl)-5-(1-hydroxyethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine (0.2 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1CCN(CC1)C=O;m1_m2_m3:Cl, Reagents are:m1_m2_m3:CO, and Products are 0:Cl.CC1=C(C(=NC(=N1)C1=CC=CC=C1)C1=CC(=CC=C1)[N+](=O)[O-])CN1CCN(CC1)C=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 6-methyl-5-(4-formylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine (4.5 g) and hydrochloric acid (2 ml) in methyl alcohol (45 ml) was stirred at 10° C. for 2 hours. The resulting precipitates were collected by filtration, washed with methyl alcohol and dried in vacuo to give 6-methyl-5-(4-formylpiperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine hydrochloride (4.14 g). |
Here is a chemical reaction formula: Reactants are:m1_m6:[OH-].[Na+];m4:C=O;m2:C(C)(C)(C)C1=CC=C(C=C1)O;m5:Cl;m3:C1(=CC=CC=C1)O, Reagents are:m1_m6:O;m7:C(Cl)(Cl)Cl, and Products are 0:C(C)(C)(C)C1=CC(=C(C(=C1)CO)O)CO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 50 g sodium hydroxide were dissolved in approximately 1.2 liters of water, and 150 g of 4-tert-butylphenol were added to this solution. The mixture was stirred and gently heated until the phenol dissolved. The solution was then cooled to ambient temperature. Aqueous formaldehyde (175 ml, 37 percent) was added, and the solution was stirred for four to six days at ambient temperature. Concentrated hydrochloric acid (110 ml) was added, upon which a two-phase system forms. A yellow, oily organic phase was isolated and washed with three 500 ml portions of water. Chloroform (700 ml) and 500 ml of water were added to this organic oil and the mixture was stirred. The organic phase was isolated and dried over 100 g of anhydrous magnesium sulphate. Evaporation and cooling of the chloroform solution yielded a mixture of white crystals and oil. The addition of 50-100 ml of chloroform and filtration yielded a white crystalline product, 4-tert-butyl-2,6-di(hydroxymethyl)phenol. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C)(=O)[O-].COC1=CC=C(CC2[NH2+]CCC3CCCC=C23)C=C1, Reagents are:m1_m2:C(C)(C)O, and Products are 0:C(C)(=O)[O-].COC1=CC=C(C[C@H]2[NH2+]CC[C@@H]3CCCC=C23)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Sufficient racemic (R,S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate is dissolved in isopropanol to form a 52.6% by weight (R,S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate solution. The solution is seeded at 20° C. with about 1%, relative to the weight of the solution, of (S)-acetate and is stirred at 0° C. for 2 to 3 hours. The crystallized (S)-acetate is filtered off with suction and washed with tert.-butyl methyl ether. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C(C)(=O)[O-].COC1=CC=C(C[C@@H]2[NH2+]CCC3CCCC=C23)C=C1;m1_m3_m2:[OH-].[Na+], Reagents are:m1_m3_m2:O, and Products are 0:COC1=CC=C(C[C@@H]2NCCC3CCCC=C23)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 31.7 g of (S)-1-(4-methoxybenzyl)-octahydroisoquinolinium acetate in 250 ml of water is brought by addition of concentrated sodium hydroxide solution to pH 12. The free base is extracted twice with 150 ml of diethyl ether each time. Washing of the combined extracts with water, drying over sodium sulfate and removal of the solvent in vacuo leaves 25.0 g (97.3% of theory) of (S)-1-(4-methoxybenzyl)-octahydroisoquinoline. |
Here is a chemical reaction formula: Reactants are:m2:C([O-])([O-])=O.[K+].[K+];m3_m1:CC1=[N+](C=CC(=C1C)[N+](=O)[O-])[O-];m3_m1:C(CC)O, Reagents are:, and Products are 0:CC1=[N+](C=CC(=C1C)OCCC)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: In n-propanol (42 ml) was dissolved 2,3-dimethyl-4-nitropyridine-1-oxide (841 mg). To the solution was added anhydrous potassium carbonate (2.1 g), and the mixture was stirred at 80° C. for 22 hours, followed by filtration with celite. The filtrate was concentrated, and the residue was chromatographed on a column of silica-gel (50 g), which was eluted with 5% methanol.chloroform to yield 2,3-dimethyl-4-propoxypyridine-1-oxide (360 mg) as an oily substance. |
Here is a chemical reaction formula: Reactants are:m1_m3:CC=1C(=NC=CC1OCCC)CSC=1NC2=C(N1)C=CC=C2;m2:ClC1=CC(=CC=C1)C(=O)OO, Reagents are:m1_m3:C(Cl)(Cl)Cl;m4:C(Cl)(Cl)Cl, and Products are 0:CC=1C(=NC=CC1OCCC)CS(=O)C=1NC2=C(N1)C=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 2-(3-methyl-4-propoxy-2-pyridyl)methylthiobenzimidazole (1 g) in chloroform (20 ml) was added dropwise over 10 minutes under ice-cooling m-chloroperbenzoic acid (750 mg) dissolved in chloroform (10 ml). The solution was chromatographed directly on a column of silica gel (50 g), which was eluted with ethyl acetatehexane (1:1) and then with 5% methanol-ethyl acetate. From the eluate was removed the solvent. The residue was recrystallized from acetone-ether-hexane to give 415 mg of 2-[3-methyl-4-propoxy-2-pyridyl)methylsulfinylbenzimidazole.4/5H2O as crystals, m.p. 81°-83° C. |
Here is a chemical reaction formula: Reactants are:m1:NC=1SC2=C(N1)C=CC=C2;m2:[OH-].[Na+];m3_m4_m5_m6_m7:[Na];m3_m4_m5_m6_m7:[K];m3_m4_m5_m6_m7:SC1=C(C=CC=C1)NC(=O)N, Reagents are:m9:O;m8:O;m3_m4_m5_m6_m7:C(C)(=O)O;m3_m4_m5_m6_m7:C=C1CC(=O)O1, and Products are 0:C(C(=O)C)C=1SC2=C(N1)C=CC=C2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The water-moist 2-mercaptophenylurea obtained according to European Pat. No. 0,039,483, Example 1, paragraph 1, by reacting 150 parts of 2-aminobenzothiazole with 150 parts of sodium hydroxide and working up the mixture with water, or an appropriate amount of the sodium or potassium salt of the said 2-mercaptophenylurea, is dissolved in 500 parts of 50% strength acetic acid, and 118 parts of diketene are then added dropwise in the course of 2 hours at 45° to 50° C. Stirring is continued for 1 hour, after which the mixture is heated to the reflux temperature and kept at a temperature of 95° C.-100° C. for 2 hours. It is then cooled to room temperature, and the precipitated 2-acetonylbenzothiazole of the formula ##STR13## is isolated by filtration and dried in vacuo at 60° C.-80° C. 151.7 parts of a product of melting point 118° C.-119° C. are obtained; this corresponds to a yield of 79.4%, based on 2-aminobenzothiazole employed. |
Here is a chemical reaction formula: Reactants are:m1:[Na];m3:C(C)(=O)O;m2:ClC1=CC(=C(C=C1)NC(=O)N)S, Reagents are:m4:O;m5:O, and Products are 0:ClC1=CC2=C(N=C(S2)C)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 112.25 parts of the sodium salt of 4-chloro-2-mercaptophenylurea, which salt is obtainable according to Example 6 of European Pat. No. 0,039,483, are suspended in 450 parts of glacial acetic acid in an autoclave. The pressure vessel is closed and heated slowly to 150° C.-160° C. in the course of 2 hours, a pressure of about 5 bar being established. The water formed is discharged continuously via a pressure release valve. The reaction is complete after 5 hours. The autoclave is cooled to room temperature and opened, the reaction mixture is allowed to run into 1000 parts of water, and the precipitated 6-chloro-2-methylbenzothiazole is isolated by filtration, washed neutral and dried in vacuo at 40° C. 85.6 parts of a product of the formula ##STR21## of melting point 85° C.-86° C. are obtained; this corresponds to a yield of 93.3% of theory, based on sodium salt employed. |
Here is a chemical reaction formula: Reactants are:m3:Cl;m1_m4_m2:NCC(=O)O;m1_m4_m2:FC1=CC=C(C(=O)Cl)C=C1, Reagents are:m5:[OH-].[Na+];m1_m4_m2:[OH-].[Na+], and Products are 0:FC1=CC=C(C(NCC(=O)O)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of glycine (15 g, 0.2 mol) in 175 mL of 5% aqueous sodium hydroxide is cooled to 10° C. to 15° C. p-Fluorobenzoyl chloride (31.6 g, 0.2 mol) is then added dropwise to the mixture and stirred vigorously for 0.5 hour while maintaining the temperature of the mixture of about 10° C. to 15° C. The pH of the reaction mixture is maintained at pH>9 by the dropwise addition of 50% aqueous sodium hydroxide. The mixture is stirred at 10° C. to 15° C. for two hours and the resulting clear solution then acidified to pH-1 with concentrated HCl. The resulting product is filtered off, washed with water (2×100 mL) and air dried to give a white solid (30.8 g, 78.1%); mp=161°-163° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3:C1(CC1)C1=NOC(=N1)CNC=O;m1_m2_m5_m3:C(C)N(CC)CC;m1_m2_m5_m3:O=P(Cl)(Cl)Cl;m4_m6:C(=O)([O-])[O-].[Na+].[Na+], Reagents are:m1_m2_m5_m3:C(Cl)Cl;m4_m6:O, and Products are 0:C1(CC1)C1=NOC(=N1)C[N+]#[C-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred solution of 3-cyclopropyl-5-formylaminomethyl-1,2,4-oxadiazole (60 mmol) and triethylamine (176 mmol) in CH2Cl2 (100 ml) was charged at 0° C. dropwise with POCl3 (60 mmol). The mixture was then left for 30 min. with stirring at 0° C., whereafter a solution of Na2CO3 (60 mmol) in H2O (50 ml) was added. The mixture was heated to room temperature, whereafter the organic phase was separated, dried and evaporated in vacuo. The residue was treated with ether, decanted, and the solution was evaporated to give the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m4_m6:C(=O)([O-])[O-].[Na+].[Na+];m1_m2_m5_m3:C1(CC1)C1=NC(N(O1)C)NC=O;m1_m2_m5_m3:C(C)N(CC)CC;m1_m2_m5_m3:O=P(Cl)(Cl)Cl, Reagents are:m4_m6:O;m1_m2_m5_m3:C(Cl)Cl, and Products are 0:C1(CC1)C1=NC(=NO1)C[N+]#[C-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A stirred solution of 5-cyclopropyl-3-formylamino-methyl-1,2,4-oxadiazole (60 mmol) and triethylamine (176 mmol) in CH2Cl2 (100 ml) was charged dropwise with POCl3 (60 mmol) at 0° C. The mixture was then left for 30 min. with stirring at 0° C., whereafter a solution of Na2CO3 (60 mmol) in H2O (50 ml) was added. The mixture was heated to room temperature, whereafter the organic phase was separated, dried and evaporated in vacuo. The residue was treated with ether, decanted and the solution was evaporated to give the title compound as an oil. |
Here is a chemical reaction formula: Reactants are:m3:C(C)(=O)OC(C)=O;m1:C(CCCCCCCCCCC)C1=CC=C(N)C=C1;m2:C(C)(=O)OC(C)=O, Reagents are:, and Products are 0:C(C)(=O)NC1=CC=C(C=C1)CCCCCCCCCCCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a 1-liter flask fitted with a stirrer and reflux condenser is added 137.5 grams (0.525 mole) of p-n-dodecylaniline, dissolved in 138 ml of tolune. To this is added over a 15-minute period 57.5 ml of acetic anhydride. The temperature rises from 40° to 80° C. After all the acetic anhydride is added, the reaction mixture is stirred at 40° C. for 3 hours. The reaction mixture is then cooled to yield the crude product which is recrystallized from 800 ml of methanol to give 151.1 grams of the above-named material as a solid melting at 100°-102° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)(=O)NC1=C(C=C(C=C1)CCCCCCCCCCCC)[N+](=O)[O-];m1_m2_m3:C(C)O;m1_m2_m3:[OH-].[K+], Reagents are:m4:O, and Products are 0:C(CCCCCCCCCCC)C1=CC(=C(N)C=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: In a 1-liter flask fitted with a stirrer and reflux condenser, 61.8 grams of N-acetyl-4-n-dodecyl-2-nitroaniline (prepared in Example 2b), 320 ml of ethanol and 64 ml of 40% aqueous potassium hydroxide solution are heated for 1 hour under reflux. The reaction mixture is cooled and then poured into 1.5 liters of water. The crude product is isolated by filtration, washed repeatedly with cold water and recrystallized from methanol. The above-named product is isolated as a solid melting at 69°-71° C. in a yield of 45 grams. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C1=CC=CC=C1)(=O)Cl;m1_m2:N1=CC=CC=C1;m3:C(C1=CC=CC=C1)=O, Reagents are:, and Products are 0:[Cl-].C(C1=CC=CC=C1)(=O)OC(C1=CC=CC=C1)[N+]1=CC=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Benzoyl chloride 3.0 g (0.021 mol) and 1.69 g (0.021 mol) pyridine were mixed together under nitrogen and allowed to react at room temperature overnite. Benzaldehyde 2.23 g (0.021 mol) was added and the mixture was allowed to stand at ambient temperature for 4 days. Recrystallization from ethanol:ether gave 4.27 g (0.013 mol), 62%, α-benzoyloxybenzylpyridinium chloride, mp 174.5°-176.5°. |
Here is a chemical reaction formula: Reactants are:m1_m2:C(C1=CN=CC=C1)(=O)OCC;m1_m2:C(C1=CC=CC=C1)(=O)OCCl, Reagents are:, and Products are 0:[Cl-].C(C1=CC=CC=C1)(=O)OC[N+]1=CC(=CC=C1)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 3.00 g (0.02 mol) ethyl nicotinate and 3.50 g (0.02 mol) chloromethyl benzoate was heated at 70° under nitrogen for 10 hrs. Trituration in anhydrous ether and recrystallization from ethanol-ether gave 2.18 g (0.007 mol), 35%, 1-benzoyloxymethyl-3-carboethoxypyridinium chloride, mp 138°-141°; ir (KBr) 1730 cm-1 ; pmr (CDCl3) δ 1.43 (t, 3H), 4.47 (q, 2H), 7.7-7.3 (m, 5H), 8.2-7.95 (m, 2H), 9.17-8.50 (m, 4), 10.0 (bs, 1H) and 10.2 (bd, 1H) ppm. |
Here is a chemical reaction formula: Reactants are:m3:[OH-].[K+];m1_m2_m4:OC1=CC=C(C=C1)C(C)=O;m1_m2_m4:BrCCCCl, Reagents are:m1_m2_m4:CO, and Products are 0:ClCCCOC1=CC=C(C=C1)C(C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of p-hydroxyacetophenone (50.7 g, 0.37 mol) and 1-bromo-3-chloropropane (160 ml, 1.5 mol) in methanol (250 ml) was added portionwise potassium hydroxide (63 g, 1.12 mol). The mixture was stirred at reflux for 24 hours, cooled to room temperature, filtered through Celite and evaporated in vacuo. The residual semi-solid was diluted with diethyl ether (500 ml) and washed with H2O (2×300 ml). The ether solution was dried over MgSO4, filtered and evaporated in vacuo to give p-chloropropoxy acetophenone as a liquid in 68% yield (53.38 g). 1H NMR (CDCl3): δ7.98-7.89 (d, J=8.9 Hz, 2H), 7.02-6.92 (d, J=8.9 Hz, 2H), 4.16 (t, J=5.9 Hz, 2H), 3.75 (t, J=6.4 Hz, 2H), 2.52 (s, 3H), 2.34-2.16 (m, 2H). |
Here is a chemical reaction formula: Reactants are:m1_m2:ClCCCOC1=CC=C(C=C1)C=1N=C2N(C=CC=C2)C1, Reagents are:m1_m2:C(CCC)NCCCC, and Products are 0:C(CCC)N(CCCC)CCCOC1=CC=C(C=C1)C=1N=C2N(C=CC=C2)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A suspension of 2-(4-chloropropoxyphenyl)imidazo[1,2-a]-pyridine (5.2 g, 14 mmol) in dibutylamine (30 ml) was stirred at reflux for 5 hours. The excess dibutylamine was removed by distillation and the resulting oil was flash chromatographed (silica gel, 9:1 CH2Cl2 : acetone) to give the free base of the title compound (5.1 g, 93% yield) as an oil. The HCl salt was prepared by dropwise addition of concentrated hydrochloric acid to a solution of the free base in methanol, concentrated and recrystallized from methanol acetone to yield 2-(4-dibutylaminopropoxyphenyl)imidazo- [1,2-a]pyridine as a white crystalline solid, mp 179° C. to 183° C. IR(KBr): 3400, 2620, 1650, 1620 cm-1. MS: 380 (MH+). 1H NMR (CD3OD): δ8.80 (d, J=8 Hz, 1H), 8.52 (s, 1H), 7.92-7.49 (m, 5H), 7.18 (d, J=8 Hz, 2H), 4.23 (t, J=4.6 Hz, 2H), 3.50-3.13 (m, 6H), 2.25 (m, 2H), 1.82-1.34 (m, 8H), 1.01 (m, 6H). |
Here is a chemical reaction formula: Reactants are:m5:C(CCC)NCCCC;m3:BrBr;m4:CC=1C(=NC=CC1)N;m1_m2:OC1=CC=C(C=C1)C(CC)=O;m1_m2:BrCCCCl, Reagents are:, and Products are 0:C(CCC)N(CCCC)CCCOC1=CC=C(C=C1)C=1N=C2N(C=CC=C2C)C1C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: p-Hydroxypropiophenone (50 g, 0.33 mmol) was reacted with 1-bromo-3-chloropropane and the resulting compound reacted with bromine as described in Example 1. The resulting compound was reacted with 3-methyl-2-aminopyridine (1.7 g, 16 mmol) and the product reacted with dibutylamine as described in Example 1 to produce 2.4 g. (62% yield) of the title compound as the HCl salt, mp 202° C. to 204° C. IR(KBr): 3420, 2620, 1650 1605cm-1. MS: 408 (M+). 1H NMR (CD3OD): δ8.58 (d, J=6.5 Hz, 1H), 7.85-7.71 (m, 3H), 7.48 (t, J=6.7 Hz, 1H), 7.22 (d, J=8.7 Hz, 2H), 4.26 (t, J=5.8 Hz, 2H), 3.52-3.16 (m, 6H), 2.75 (s, 3H), 2.73 (s, 3H), 2.33 (m, 2H), 1.87-1.36 (m, 8H), 1.02 (m, 6H). |
Here is a chemical reaction formula: Reactants are:m1_m2:ClCCCOC1=CC=C(C(=O)C=2N=C3N(C=CC=C3C)C2)C=C1, Reagents are:m1_m2:C(CCC)NCCCC, and Products are 0:C(CCC)N(CCCC)CCCOC1=CC=C(C(=O)C=2N=C3N(C=CC=C3C)C2)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2-(4-chloropropoxybenzoyl)-8-methylimidazo-[1,2-a]pyridine (2,4 g, 6.0 mmol) in dibutylamine (30 ml) was stirred at reflux for 8 hours. The excess dibutylamine was removed by distillation and the resulting oil was flash chromatographed (silica gel, acetone) to give the free base of the title compound (2.5 g, 100% yield) as a thick oil. The HCl salt was prepared by dropwise addition of concentrated hydrochloric acid to a solution of the title compound in methanol, concentrated and recrystallized from methanol-acetone, mp 159° C. to 161° C. IR(KBr): 3420, 1650cm-1. MS: 421 (M+). 1H NMR (CD3OD): δ8.89 (s, 1H), 8.72 (d, J=6.6 Hz, 1H), 8.15 (d, J=8.9 Hz, 2H), 7.89 (d, J=7.3 Hz, 1H), 7.48 (t, J=6.9 Hz, 1H), 7.21 (d, J= 8.9 Hz, 2H), 4.29 (t, J=7 Hz, 2H), 3.26 (m, 6H), 2.73 (s, 3H), 2.33 (m, 2H), 1.79-1.35 (m, 8H), 1.02 (m, 6H). |
Here is a chemical reaction formula: Reactants are:m1_m2:COC1=CC=C(C=C1)C(O)C(=C(Cl)Cl)Cl;m1_m2:S(O)(O)(=O)=O.CO;m3:Cl, Reagents are:m4:O, and Products are 0:COC(/C(=C/C1=CC=C(C=C1)OC)/Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: p-Methoxyphenyltrichlorovinyl carbinol (2.3 g, 8.6 millimoles) is added to a 40:60 (V/V) solution of sulfuric acid/methanol which is stirred under nitrogen at reflux (100° C.-106° C.) for 7 minutes. Rapid evolution of hydrogen chloride is noted and ceases after this period. The solution is cooled and poured into 40 ml of water, followed by extraction twice with 20 ml of methylene chloride each time. The organic phase is dried over MgSO4, filtered and rotary evaporated giving z-methyl-2-chloro-3-(4'-methoxyphenyl)propenoate (1.92 g, 8.5 millimoles) in 99 percent yield as a light yellow oil which crystallized on standing (M.P.=68° C.-70° C., M.P.LIT1 =67° C.-70° C.): 'H NMR (CDCl3) δ 7.24 (4H, ab quartet), 7.72 (1H, s), 3.76 (3H, s), 3.68 (3H, s); 13C NMR (CDCl3) δ 164.0, 161.1, 136.7, 132.6, 125.4, 119.0, 113.9, 55.2, 53.0. |
Here is a chemical reaction formula: Reactants are:m2:Cl;m1_m3:ClC1=CC=C(C=C1)C(O)C(=C(Cl)Cl)Cl;m1_m3:COC(/C(=C/C1=CC=C(C=C1)OC)/Cl)=O, Reagents are:, and Products are 0:COC(/C(=C/C1=CC=C(C=C1)Cl)/Cl)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: p-Chlorophenyltrichlorovinyl carbinol (6.0 g, 22.0 millimoles) is added to a refluxing solution of methanolic sulfuric acid (30 ml as noted in Example 4). Hydrogen chloride evolution is noted during the stirring procedure for 45 minutes. The mixture is cooled and has a workup as in Example 4, which affords z-methyl-2-chloro-3-(4'-chlorophenyl)propenoate (4.7 g, 20.4 millimoles) in 93 percent yield (M.P.=78° C.-80° C.): 'H NMR (CDCl3) δ 7.77 (1H, s), 7.45 (4H, ab quartet), 3.81 (3H, s); 13C NMR (CDCl3) δ 163.5, 136.1, 135.8, 131.6, 131.3, 128.8, 122.3, 53.4. Analysis calculated for: C, 52.01; H, 3.50. Found: C, 51.85; H, 3.42. |
Here is a chemical reaction formula: Reactants are:m0_m3:[N+](=O)([O-])C1=C(C=CC=C1)CC(C(=O)O)=O;m1:CN(C=O)C;m2:S(=O)(Cl)Cl, Reagents are:, and Products are 0:OC(C(=O)O)CC1=C(C=CC=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: To magnetically stirred N,N-dimethylformamide (23 ml., 297.3 mmol) cooled in ice was slowly added dropwise thionyl chloride (139 ml., ca. 1.91 mol). A solution of (+)-α-hydroxy-2-nitrobenzenepropanoic acid [11.60 g., 54.9 mmol, [α]D25 +49.94° (c 2.465, 95% EtOH)], obtained from the chiral reduction of 2-nitro -α-oxobenzenepropanoic acid described in Example 1, in dichloromethane (133 ml.) was then added dropwise to the cold Vilsmeier reagent. The ice bath was removed and the solution, protected from moisture, was left at room temperature (25° C.) for 18 hours. The resulting yellow solution was evaporated to syrup. The syrup was dissolved in dichloromethane and the solution was poured cautiously onto stirred ice. The mixture was stirred for one hour during which time it warmed to room temperature. The organic phase was separated, washed (×3) with water and dried (MgSO4). Evaporation gave a syrup which was subjected to an oil pump vacuum for 0.5 hour. The syrup was dissolved in ether and 2,6-dimethylpiperidine was added to approximate neutrality (ca. pH 8 by pH paper). The crude titled compound (12.40 g., 66%) crystallized readily, m.p. 148°-153° C. Three crystallizations (with decolorization) from methanol-ether gave 6.01 g. (32% of pure product, m.p. 164°-167° C. dec., [α]D25 -41.49° (c 1.005, 95% EtOH). |
Here is a chemical reaction formula: Reactants are:m1_m2:CC1NC(CCC1)C.ClC(C(=O)O)CC1=C(C=CC=C1)N;m1_m2:[OH-].[Na+];m3:Cl, Reagents are:m4:CN(C)C=O, and Products are 0:N1[C@@H](CC2=CC=CC=C12)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: (+)-α-Chloro-2-aminobenzenepropanoic acid 2,6-dimethylpiperidine salt (1.25 g., 4.00 mmol) was added to magnetically stirred N sodium hydroxide (4 ml.) under nitrogen. The solution was stirred under nitrogen overnight at room temperature. The pH was adjusted to a value between 2 and 3 (pH paper) with conc. hydrochloric acid while cooling in ice. The crystalline precipitate was collected and washed with several aliquots of ice cold water. The product was dried briefly under vacuum over phosphorus pentoxide and then stirred with ether. The product was dried over phosphorus pentoxide at 56° C. for several hours under oil pump vacuum to give 0.48 g. (74%) of the title compound, m.p. 155°-157° C., [α]D25 +36.09° (c 0.87, DMF). |
Here is a chemical reaction formula: Reactants are:m3_m5:[N+](=O)([O-])C1=C(C=CC=C1)CC(C(=O)O)=O;m1_m2_m4:N1[C@H](C(=O)O)CCC1;m1_m2_m4:[BH4-].[Na+], Reagents are:m3_m5:O1CCCC1;m1_m2_m4:O1CCCC1, and Products are 0:OC(C(=O)O)CC1=C(C=CC=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: L-(-)-proline (7.50 g., 65.1 mmol) and sodium borohydride (2.46 g., 65.1 mmol) were stirred in tetrahydrofuran under nitrogen for sixteen hours. Recrystallized o-nitrophenylpyruvic acid (14.17 g., 76.5 mmol) in tetrahydrofuran (50 ml.) was added dropwise, and the resulting solution was stirred at room temperature for six days. The solvent was evaporated and the resulting gum was stirred with 10% aqueous HCl (200 ml.) for 4.5 hours. A small amount of solid was filtered to provide nearly racemic α-hydroxy-2-nitrobenzenepropanoic acid, 1.25 g., m.p. 98°-102° C., [α]D25 -4.21° (c 2.045, EtOH). |
Here is a chemical reaction formula: Reactants are:m3:CC(C)(C)C(=O)OC=1C=CC(=CC1OC(=O)C(C)(C)C)C(CNC)O.Cl;m1_m4_m5_m6_m2_m7:IC1=C(C=CC=C1)S(=O)(=O)N;m1_m4_m5_m6_m2_m7:P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m1_m4_m5_m6_m2_m7:CN(C=O)C;m1_m4_m5_m6_m2_m7:C(C)N(CC)CC;m1_m4_m5_m6_m2_m7:Cl[Pd]Cl;m1_m4_m5_m6_m2_m7:[Cu]I, and Products are 0:C1(=CC=CC=C1)S(=O)(=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 28.3 g (0.1 mole) of 2-iodophenylsulfonamide in 350 ml of dimethylformamide and 100 ml of triethylamine are added 1.0 g of palladium dichloro-bis(triphenylphosphite) complex, PdCl2 [P(C6H5)3 ]2, and 0.5 g of copper(I) iodide (CuI). Gaseous propine is then introduced into this solution until the starting material is completely reacted. The reaction mixture is filtered and the residue is concentrated in vacuo and then taken up in water. The precipitate is isolated and dried. Recrystallisation from ethyl acetate/hexane yields 15.6 g (80%) of 2-propyn-1-yl)phenylsulfonamide with a melting point of 147°-149° C. |
Here is a chemical reaction formula: Reactants are:m2:[Sb](Cl)(Cl)(Cl)(Cl)Cl;m1_m3:ClC(C(F)(F)F)(OC1=CC=C(C=C1)Cl)Cl;m1_m3:F, Reagents are:, and Products are 0:ClC(C(F)(F)F)(OC1=CC=C(C=C1)Cl)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 500 ml polytetrafluoroethylene reactor equipped with stirrer, thermometer and reflux condenser is charged with 55.9 g (0.2 mol) of 4-(1,1-dichloro-2,2,2-trifluoroethoxy)chlorobenzene in 100 ml of hydrogen fluoride. 3.0 g (0.01 mol; corresponding to 5 mol%) of antimony pentachloride are added at a temperature in the range from -5° C. to 0° C. The resultant hydrogen chloride is removed from the reactor through the reflux condenser. After 20 minutes at 0° C., the evolution of hydrogen chloride ceases. Excess hydrogen fluoride is removed by distillation, the residue is dissolved in 200 ml of methylene chloride and the solution is extracted with water. The organic phase is separated by distillation, affording 47.3 g (89.8% of theory) of 4-(1-chloro-1,2,2,2-tetrafluoroethoxy)chlorobenzene. Boiling point 181° C., nD25 =1.4362. |
Here is a chemical reaction formula: Reactants are:m3:[Sb](Cl)(Cl)(Cl)(Cl)Cl;m1:ClC1(C(C=CC=C1)SCC(F)(F)F)Cl;m2:F, Reagents are:, and Products are 0:ClC1=C(C=CC=C1)SC(C(F)(F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 500 ml polytetrafluoroethylene reactor equipped with stirrer, thermometer and reflux condenser is charged with 24.7 g (0.094 mol) of 1,1-dichloro-2,2,2-trifluoroethylthiobenzene which are subsequently condensed with 50 g of hydrogen fluoride. 4.2 g (0.014 mol; corresponding to 15 mol%) of antimony pentachloride are added at a temperature of 20° C. The resultant hydrogen chloride is removed from the reactor through the reflux condenser. After 3 hours a further 1.4 g (5 mol%) and after 4 hours a further 2.8 g (10 mol%) of antimony pentachloride are added. After a total reaction time of 5 hours, the hydrogen fluoride is removed by distillation, the residue is dissolved in 150 ml of methylene chloride and the solution is extracted with water. The solution is separated by distillation, affording 1-chloro-1,2,2,2-tetrafluoroethylthiobenzene. Boiling point 178°-179° C., nD20 =1.4732. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C)O;m1_m2_m3_m4:C(C)(=O)OC(C1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)OC(C)=O)OC(C)=O;m1_m2_m3_m4:S(O)(O)(=O)=O, Reagents are:m1_m2_m3_m4:O, and Products are 0:C(C)(=O)OC(C(F)(F)F)(C(F)(F)F)C1=CC=C(C=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 130 ml of ethanol are added 60 g (0.15 mole) of α,α-bis-acetyloxy-4-[1-(acetyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]toluene and 13.5 ml of concentrated sulfuric acid in 135 ml of water. The resulting solution is stirred and heated at reflux for thirty minutes. The solution is then cooled and extracted with 1 liter of ether to obtain an ether solution which is washed with water and a saturated sodium bicarbonate solution until the washes were basic. The ether solution is dried with anhydrous magnesium sulfate, filtered and evaporated at reduced pressure to give 42 g of 4-[1-(acetyloxy)-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]benzaldehyde. This compound was not further purified but was used directly in the next step. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:FC(C(C(F)(F)F)(O)C1=CC=C(C=C1)CCC(=O)O)(F)F;m1_m5_m2:[N+](=O)(O)[O-];m4:O;m3:[N+](=O)(O)[O-], Reagents are:m1_m5_m2:S(O)(O)(=O)=O, and Products are 0:[N+](=O)([O-])C1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 63.2 g (0.20 mole) of 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid in 160 ml of concentrated sulfuric acid is added 40 ml of fuming nitric acid (90%) dropwise with stirring at 0°-5°. Following the nitric acid addition the solution is allowed to warm to 20° with stirring over a 1-hour period. The solutionis then added to a mixture of ice and water and allowed to stand for 18 hours. A precipitate results and is filtered, washed with water and dissolved in ether to obtain a solution which is washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated to give a residual solid. The residual solid is recrystallized from chlorobutane to give 40 g of 2-nitro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid having a melting point of 115°-116°. |
Here is a chemical reaction formula: Reactants are:m1:ClS(=O)(=O)O;m2:FC(C(C(F)(F)F)(O)C1=CC=C(C=C1)CCC(=O)OC)(F)F, Reagents are:, and Products are 0:ClS(=O)(=O)C1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To excess chlorosulfonic acid cooled with an ice-acetone bath can be added methyl 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoate with stirring. The solution should be stirred for several hours. Addition of the reaction mixture to ice and isolation of the product will give 2-chlorosulfonyl-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid, methyl ester. Reduction of 2-chlorosulfonyl-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid, methyl ester with zinc in acetic acid followed by isolation of the product will give 2-mercapto-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid, methyl ester. |
Here is a chemical reaction formula: Reactants are:m1:ClS(=O)(=O)C1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)OC, Reagents are:m3:[Zn];m2:C(C)(=O)O, and Products are 0:SC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To excess chlorosulfonic acid cooled with an ice-acetone bath can be added methyl 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoate with stirring. The solution should be stirred for several hours. Addition of the reaction mixture to ice and isolation of the product will give 2-chlorosulfonyl-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid, methyl ester. Reduction of 2-chlorosulfonyl-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid, methyl ester with zinc in acetic acid followed by isolation of the product will give 2-mercapto-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid, methyl ester. |
Here is a chemical reaction formula: Reactants are:m1_m3:CSC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)OC;m2:Cl, Reagents are:m1_m3:[OH-].[Na+], and Products are 0:CSC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 3,4-dihydro-7-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-2H-1-benzothiapyran-2-one in dimethylacetamide can be added a one molar excess of sodium hydroxide in methanol. The resulting solution should be heated, and a one molar excess of methyl iodide should be added with stirring. From the resulting reaction mixture can be isolated 2-methylthio-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid, methyl ester. This ester should be dissolved in an aqueous solution of sodium hydroxide to obtain a solution which will be heated on a steam bath. Concentrated hydrochloric acid can then be added to this solution, thereby yielding a precipitate which can be isolated to give 2-methylthio-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid. |
Here is a chemical reaction formula: Reactants are:m5:FC(C(=O)C(F)(F)F)(F)F;m8:Cl;m1_m9:[Mg];m4_m10:BrC=1C=C(C=CC1)OC;m7:FC(C(=O)C(F)(F)F)(F)F;m6:FC(C(=O)C(F)(F)F)(F)F;m2_m3:BrC=1C=C(C=CC1)OC;m2_m3:BrCCBr, Reagents are:m12:O;m1_m9:O1CCCC1;m4_m10:O1CCCC1;m13:O;m11:CCOCC, and Products are 0:COC1=CC(=CC=C1)C(C(F)(F)F)(C(F)(F)F)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 13.5 g (0.55 g atoms) of sublimed magnesium chips in 25 ml of anhydrous tetrahydrofuran in a reaction flask fitted with a water-cooled condenser are added 10 g (0.05 mole) of 3-bromo-1-methoxybenzene and 0.5 ml of 1,2-dibromoethane. The resulting reaction mixture is stirred and heated gently until a reaction is initiated. To the stirred reaction mixture is added dropwise a solution of 90 g (0.48 mole) of 3-bromo-1-methoxybenzene in 250 ml of anhydrous tetrahydrofuran at such a rate that gentle reflux is maintained. The reaction mixture is stirred for an additional two hours. The resulting solution is then cooled to 0° and the reaction flask is fitted with a jacketed dropping funnel topped by a dry ice condenser. The water condenser is replaced by an additional dry ice condenser. To the jacketed dropping funnel are added 85 g (50 ml) (0.55 mole) of condensed hexafluoroacetone. The condensed hexafluoroacetone is added dropwise to the stirred solution which is cooled to 0° to -10° with an ice-acetone bath. When the addition of the hexafluoroacetone is complete, the resulting solution is allowed to warm to 20°-25° and stirring is continued for an additional 18 hours. The solution is cooled to 0° and treated with 6N hydrochloric acid to obtain an acidic solution to which is added 1-liter of ether. The resulting ether layer is washed with water, washed with a 5% sodium bicarbonate solution, dried with anhydrous magnesium sulfate, filtered and evaporated at reduced pressure to yield a residual solid which is recrystallized from chlorobutane to give 78 g of 1-methoxy-3-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzene. |
Here is a chemical reaction formula: Reactants are:m3_m5_m6:Cl;m1_m4_m7:COC1=CC(=CC=C1)C(C(F)(F)F)(C(F)(F)F)O;m2:COC(Cl)Cl, Reagents are:m3_m5_m6:O;m1_m4_m7:ClCCl;m1_m4_m7:[Ti](Cl)(Cl)(Cl)Cl, and Products are 0:COC1=C(C=O)C=CC(=C1)C(C(F)(F)F)(O)C(F)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 31.6 g (0.12 mole) of 1-methoxy-3-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzene in 200 ml dichloromethane is added 38 g (0.2 mole) of titanium tetrachloride at 0°-5° with stirring under a nitrogen atmosphere. After the resulting solution is stirred for 15 minutes, 11.5 g (0.1 mole) of α,α-dichloromethyl methyl ether is added dropwise at 0°-5° C. Stirring is continued while the temperature of the solution is allowed to reach 20°-25° during 18 hours. The solution is then added with stirring to a solution of 100 ml 6N hydrochloric acid in 500 ml of ice and water. The resulting organic phase is separated leaving an aqueous phase which is washed with three 300 ml portions of dichloromethane. The combined dichloromethane extracts are washed with 1N hydrochloric acid and then with saturated sodium chloride solution. The dichloromethane solution is dried with anhydrous magnesium sulfate, filtered, and evaporated at reduced pressure to obtain an oily solid which is triturated with chlorobutane, filtered and recrystallized from chlorobutane to give 14.5 g of 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-(trifluoromethyl)ethyl]benzaldehyde having a melting point of 144°-146°. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:COC1=C(C=O)C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O;m1_m4_m2_m3:C(CC(=O)O)(=O)O;m1_m4_m2_m3:N1CCCCC1, Reagents are:m1_m4_m2_m3:N1=CC=CC=C1, and Products are 0:COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)C=CC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 15 g (0.05 mole) 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzaldehyde in 50 ml of pyridine are added 11 g (0.11 mole) of malonic acid and 1 g of piperidine. The solution is stirred and gradually heated to 80°. Heating and stirring are continued for 1 hour at 80°. The solution is then heated at reflux for an additional 3 hours, cooled, and evaporated at reduced pressure to obtain a residual oil which is extracted into ether. The resulting ether solution is washed with water and 1N hydrochloric acid, dried with anhydrous magnesium sulfate, filtered, and evaporated at reduced pressure to obtain a residual solid which is recrystallized from chlorobutane/hexane mixed solvent to give 10.5 g of 3-{2 -methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-propenoic acid having a melting point of 138°-140°. |
Here is a chemical reaction formula: Reactants are:m2_m1:COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)C=CC(=O)O, Reagents are:m2_m1:C(C)O, and Products are 0:COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 100 ml of ethanol are added 8.8 g (0.025 mole) of 3-{2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-2-propenoic acid to produce a solution which is added to a pressure bottle and flushed with nitrogen. To the solution is added 1 g of 10% palladium on carbon. The pressure bottle is placed in a hydrogenation apparatus and pressurized to 1384 g/cm2 (50 lbs/in.2) with hydrogen. The pressure bottle is shaken until the pressure ceases dropping. The resulting solution is vented, filtered and evaporated at reduced pressure to obtain a residual solid which is recrystallized from chlorobutane o give 7.0 gm of 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid having a melting point of 116°-117°. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:CO;m1_m4_m2_m3:COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)O;m1_m4_m2_m3:S(O)(O)(=O)=O, Reagents are:m1_m4_m2_m3:C1(=CC=CC=C1)C, and Products are 0:COC1=C(C=CC(=C1)C(C(F)(F)F)(C(F)(F)F)O)CCC(=O)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 50 ml of methanol in 50 ml toluene are added 7.0 g (0.02 mole) of 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoic acid and 1 ml of concentrated sulfuric acid. The resulting solution is stirred, heated at reflux for 18 hours, then concentrated to 20 ml at reduced pressure, and extracted with ether. The resulting ether solution is washed with 5% sodium bicarbonate solution and water. The solution is dried with anhydrous magnesium sulfate, filtered and concentrated at reduced pressure to obtain a residual solid which is recrystallized from petroleum ether to give 5.5 g of methyl 2-methoxy-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzenepropanoate having a melting point of 78°-80°. |
Here is a chemical reaction formula: Reactants are:m2_m3:Cl;m2_m3:[H][H];m1_m4:FC(C(C(F)(F)F)(O)C=1C=C(C=CC1)CC(=O)O)(F)F, Reagents are:m1_m4:O1CCCC1, and Products are 0:FC(C(C(F)(F)F)(O)C=1C=C(C=CC1)CCO)(F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To one liter of 1M borane-tetrahydrofuran complex was added a solution of 100 g (0.33 mole) of 3-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]benzeneactic acid in 200 ml of tetrahydrofuran. The solution is refluxed for 16 hours under nitrogen. The solution is then refluxed with 400 ml of 6N hydrochloric acid until evolution of hydrogen is complete. The mixture is filtered and evaporated. The residue is refluxed with 500 ml of methanol containing 10 ml of concentrated hydrochloric acid until methyl borate is no longer evolved. The solution is evaporated, and the residue is distilled at 110°-115° (0.7 mm) to give 37 g of 2-{3-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}ethanol. |
Here is a chemical reaction formula: Reactants are:m1_m2:[N+](=O)([O-])C=1C=C(C2=C(CCO2)C1)[N+](=O)[O-];m1_m2:NCCO, Reagents are:m3:O, and Products are 0:OCCNC1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])CCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.29 Mole (60.9 g) of 2,3-dihydro-5,7-dinitrobenzofuran is added in small portions at room temperature to 122 ml of 2-aminoethanol. After the addition is complete, the reaction medium is brought for 15 minutes to 95° C. 500 ml of water are added; after the mixture is cooled, the expected product is drained, and this, after being made into a paste in water and recrystallized from 75 ml of 96° strength ethanol, melts at 115° C. |
Here is a chemical reaction formula: Reactants are:m1:[N+](=O)([O-])C=1C=C(C2=C(CC(O2)C)C1)[N+](=O)[O-];m3:COCCO;m2:N, Reagents are:m4:O, and Products are 0:NC1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])CC(C)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 0.39 Mole (88 g) of 2,3-dihydro-5,7-dinitro-2-methylbenzofuran, prepared according to J.A.C.S. 80, p. 4711-4714 (1958), is suspended in 1.1 l of 20% strength ammonia solution and 600 ml of Methyl Cellosolve. After 18 hours' heating at 70° C., the reaction mixture is cooled. The precipitate formed is drained and, after being made into a paste in water until neutral and then dried under vacuum, is recrystallized from 170 ml of dioxane. After being dried under vacuum, 0.30 mole (72 g) of the expected product is obtained; it melts at 177° C. |
Here is a chemical reaction formula: Reactants are:m1_m4_m6:NC1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])CCO;m2_m3_m5:O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+];m2_m3_m5:[S], Reagents are:m1_m4_m6:C(C)(C)O;m1_m4_m6:O;m2_m3_m5:O, and Products are 0:NC1=C(C=C(C=C1N)[N+](=O)[O-])CCO, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 0.119 mole (27 g) of 2-(2-amino-3,5-dinitrophenyl)ethanol obtained in Example 1 in 67.5 ml of isopropanol to which an equal volume of water has been added, a solutionof 38.4 g of sodium sulphide nonahydrate and 5.4 g of sulphur in 10 ml of water is added dropwise at 60°-65° C. Heating is maintained for 20 minutes after the addition is complete. When the mixture is cooled, a precipitate of the expected product is obtained, and this is drained, made into a paste in water and then recrystallized from 96° strength alcohol. It melts at 172° C. |
Here is a chemical reaction formula: Reactants are:m4:ClCCCCl;m3:[Li]P(C1=CC=CC=C1)C1=CC=CC=C1;m2:C(CCC)[Li];m1:P(C1=CC=CC=C1)C1=CC=CC=C1, Reagents are:m7:O1CCCC1;m6:O;m5:C(C)OCC, and Products are 0:P(C1=CC=CC=C1)(C1=CC=CC=C1)CCCCl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a 500 mL round bottom flask there was added 400 mL of dry tetrahydrofuran followed by 0.081 mole of HPPh2. The mixture was cooled to 0° C. and 0.081 mole of n-butyl lithium was slowly added to generate LiPPh2 ; this was slowly warmed to room temperature and stirred for about one hour. The solution was transferred to a dropping funnel and added dropwise to a flask containing 100 mL of 1,3-dichloropropane dissolved in 100 mL of diethyl ether. After stirring overnight the mixture was hydrolyzed with 25 mL of water. The organic layer was separated and the solvent removed by vacuum to leave Ph2P(CH2)3Cl that was stored under nitrogen until needed. |
Here is a chemical reaction formula: Reactants are:m2:CN1CCOCC1;m3:Cl.COC([C@@H](N)C)=O;m4:CN1CCOCC1;m1_m5:C(C)(C)(C)OC(=O)N[C@@H](CC1=C(C=C(C=C1C)O)C)C(=O)O, Reagents are:m1_m5:C(Cl)Cl, and Products are 0:CC(C)(OC(=O)NC(CC1=C(C=C(C=C1C)O)C)C(=O)N[C@H](C)C(=O)OC)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Racemic t-butoxycarbonyl 2,6-dimethyltyrosine (3.9 g, 10 mmoles) was dissolved in 30 ml of CH2Cl2 by adding 1.12 ml (10 mmoles) of NMM. After bringing this mixture to reflux it was cooled to -30° C. and 1.32 ml (10 mmoles) of IBCF were added to this stirred solution. The temperature was allowed to rise to -15° C. and then lowered to -50° C. (D) alanine methyl ester hydrochloride (1.54 g, 11 mmoles) was added to the solution followed by 1.3 ml (11 mmoles) of NMM. The mixture was allowed to warm to room temperature and stand for 16 hours. The majority of the CH2Cl2 was removed under reduced pressure. Ethyl acetate (200 ml) was added and this solution was washed twice with 100 ml portions of 0.5 molar KHSO4, once with 100 ml of H2O and dried over MgSO4. Removal of all solvent gave 3.9 g of the mixture of diastereomers. Recrystallization of this material from Skelly B/CH2Cl2 produced 1.6 g (4.2 mmoles) of diastereomer F. Removal of the solvent from the filtrate gave 1.3 g (3.3 mmoles) of diastereomer S contaminated by less than 10% of diastereomer F. |
Here is a chemical reaction formula: Reactants are:m0_m1:CC(C)(OC(=O)NC(CC1=C(C=C(C=C1C)O)C)C(=O)N[C@H](C)C(=O)OC)C, Reagents are:m2:C(Cl)(Cl)Cl, and Products are 0:CC(C)(OC(=O)N[C@@H](CC1=C(C=C(C=C1C)O)C)C(=O)N[C@H](C)C(=O)O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared by the methods of Example 9 using diastereomer F of the title compound of Example 6. [α]D -21.7 (CHCl3) |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(Cl)Cl;m1_m2_m3:CC(C)(OC(=O)N[C@@H](CC1=C(C=C(C=C1C)O)C)C(=O)N[C@H](C)C(=O)O)C;m1_m2_m3:CN1CCOCC1;m4:C1(=CC=CC=C1)CCCN, Reagents are:m5:CCOC(=O)C, and Products are 0:CC(C)(OC(=O)N[C@@H](CC1=C(C=C(C=C1C)O)C)C(=O)N[C@H](C)C(=O)NCCCC1=CC=CC=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A CH2Cl2 solution (100 ml) of the title compound from Example 9, (16.6 g, 43.6 mmole) was charged with 4.4 g (43.6 mmoles) of NMM and cooled to -45° C. To this solution was added 5.7 g (43.6 mmole) of IBCF and the mixture warmed to 10° C. The solution was then cooled to -25° C. before adding 7.4 g (54.5 mmole) of 3-phenylpropylamine. After allowing the reaction to warm to room temperature and stand overnight, it was diluted with 300 ml of EtOAc and extracted with three 100 ml portions of 0.5N KHSO4. The combined aqueous washes were extracted with 100 ml of EtOAc and this extract was combined with the original organic phase. The combined organic was then washed with one 150 ml portion of brine before drying it over Na2SO4. All solvent was removed under reduced pressure to give the title product as a foam. This material was chromatographed to give 10 g (46%) of a compound identical to diastereomer S of Example 3. |
Here is a chemical reaction formula: Reactants are:m0_m1:Cl.CC1=C(C[C@H](N)C(=O)N[C@H](C)C(=O)O)C(=CC(=C1)O)C, Reagents are:m2:CO, and Products are 0:Cl.CC1=C(C[C@H](N)C(=O)N[C@H](C)C(=O)NCCCC2=CC=CC=C2)C=CC(=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The title compound was prepared by the method of Example 4 from diastereomer F of the title compound of Example 11, Route B. [α]D -23.8 (MeOH) |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1=C(C(=CC=C1)C)CCCN1C(C2=CC=CC=C2C1=O)=O;m1_m2_m3:C(C)O;m1_m2_m3:NN, Reagents are:, and Products are 0:CC1=C(C(=CC=C1)C)CCCN, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A 10 g (34.4 mmole) sample of the title compound of Example 33 was refluxed for 2 hours in 150 ml of ethanol containing 1.2 g (36.7 mmole) of 97% hydrazine. After concentrating the solution, the white crystalline residue was mixed with 100 ml of 10% NaOH and 100 ml of ether. The aqueous phase was separated and extracted with another 100 ml portion of ether. The combined ether extracts were than washed with water, dried over MgSO4 and stripped of all solvent under reduced pressure to yield 3.3 g (59%) of the product as an oil. This material was used without further purification. |
Here is a chemical reaction formula: Reactants are:m2_m3_m4:N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O;m2_m3_m4:ON1N=NC2=C1C=CC=C2;m2_m3_m4:C1(CCCCC1)N=C=NC1CCCCC1;m1_m5:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)O)=N/OC1C(NCC1)=O, Reagents are:m1_m5:O1CCCC1, and Products are 0:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O)=N/OC1C(NCC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 3.25 g of (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid are dissolved in 200 ml of tetrahydrofuran, and 3.14 g of benzhydryl 7β-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylate, 1.03 g of 1-hydroxybenzotriazole and 1.57 g of dicyclohexylcarbodiimide are added thereto. The mixture is stirred at room temperature for 2 hours. Insoluble materials are filtered off, and the filtrate is concentrated to dryness under reduced pressure. The residue is dissolved in ethyl acetate, and washed with 1% hydrochloric acid, 5% aqueous sodium bicarbonate solution and an aqueous saturated sodium chloride solution, successively. The ethyl acetate solution is then dried and concentrated to dryness under reduced pressure. The residue thus obtained is purified by silica gel chromatography (solvent, ethyl acetate:benzene=5:2). 3.7 g of benzhydryl 7β-{(Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetamido}-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]- 3-cephem-4-carboxylate are obtained. |
Here is a chemical reaction formula: Reactants are:m2_m3_m4:N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O;m2_m3_m4:ON1N=NC2=C1C=CC=C2;m2_m3_m4:C1(CCCCC1)N=C=NC1CCCCC1;m1_m5:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)O)=N/OC1C(N(CC1)C)=O, Reagents are:m1_m5:O1CCCC1, and Products are 0:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)N[C@H]1[C@@H]2N(C(=C(CS2)CSC2=NN=NN2C)C(=O)OC(C2=CC=CC=C2)C2=CC=CC=C2)C1=O)=N/OC1C(N(CC1)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1.5 g of (Z)-2-(2-tritylaminothiazol-4yl)-2-[(1-methyl-2-pyrrolidon-3-yl)oxyimino]acetic acid are dissolved in 50 ml of tetrahydrofuran, and 1.4 g of benzhydryl 7β-amino-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylate, 0.6 g of 1-hydroxybenzotriazole and 0.92 g of dicyclohexylcarbodiimide are added thereto. The mixture is stirred at room temperature for 2 hours. Then, the reaction mixture is treated in the same manner as described in Example 3-(1). 1.58 g of benzhydryl 7β-{(Z)-2-(2-tritylaminothiazol-4-yl)-2-[(1-methyl-2-pyrrolidon-3-yl)oxyimino]acetamido}-3-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylate are obtained. |
Here is a chemical reaction formula: Reactants are:m4:O;m2:C([O-])([O-])=O.[K+].[K+];m1_m5:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/O;m3:BrC1C(NCC1)=O, Reagents are:m1_m5:CS(=O)C, and Products are 0:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/OC1C(NCC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 15.8 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-hydroxyiminoacetate are dissolved in 70 ml of dimethylsulfoxide, and 5.8 g of anhydrous potassium carbonate are added thereto. The mixture is stirred at room temperature for 20 minutes. 6.6 g of 3-bromo-2-pyrrolidone are added to said mixture, and the mixture is stirred at room temperature for 20 hours. The mixture is poured into 800 ml of water, and crystalline precipitates are collected by filtration and washed with water. The crystals are dissolved in chloroform, washed with water and then dried. Then, the chloroform solution is evaporated under reduced pressure to remove solvent. 100 ml of ethyl acetate are added to the residue, and allowed to stand at room temperature. Crystalline precipitates thus obtained are collected by filtration and dried. 16.0 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetate are obtained. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/OC1C(NCC1)=O;m1_m3_m2:[OH-].[Na+], Reagents are:m1_m3_m2:CO, and Products are 0:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)O)=N/OC1C(NCC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 16.0 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetate are added to a mixture of 160 ml of methanol and 30 ml of an aqueous 2N sodium hydroxide solution, and the mixture is refluxed for 30 minutes under heating. After cooling, crystalline precipitates are collected by filtration and washed with methanol. The crystals are suspended in 30 ml of water. Then, the suspension is adjusted to pH 3 with 2N hydrochloric acid. Crystalline precipitates are collected by filtration and dried. 11.4 g of (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid are obtained. |
Here is a chemical reaction formula: Reactants are:m2:C([O-])([O-])=O.[K+].[K+];m4:O;m1_m5:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/O;m3:CN1C(C(CC1)Br)=O, Reagents are:m1_m5:CS(=O)C, and Products are 0:C(C1=CC=CC=C1)(C1=CC=CC=C1)(C1=CC=CC=C1)NC=1SC=C(N1)/C(/C(=O)OCC)=N/OC1C(N(CC1)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2.7 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-hydroxyiminoacetate are dissolved in 12 ml of dimethylsulfoxide, and 1.0 g of anhydrous potassium carbonate is added thereto under nitrogen gas atmosphere. The mixture is stirred at room temperature for 10 minutes. 1.2 g of 1-methyl-3-bromo-2-pyrrolidone are added to the mixture, and the mixture is stirred at room temperature for 5 hours. The reaction mixture is poured into 100 ml of water, and crystalline precipitates are collected by filtration. The crystals are dissolved in ethyl acetate, and the solution is washed with water and then dried. The solution is concentrated under reduced pressure to remove solvent. Then, the residue is crystallized with isopropyl ether and collected by filtration. 2.1 g of ethyl (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(1-methyl-2-pyrrolidon-3-yl)oxyimino]acetate are obtained. |
Here is a chemical reaction formula: Reactants are:m1_m2:[C@H]([C@@H](C(=O)O)O)(C(=O)O)O, Reagents are:m1_m2:CO, and Products are 0:C([C@@H](O)CC(=O)O)(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: One of the intermediates, (S)-1-methyl-3-pyrrolidinol, was synthetized with retention of optical purity as shown in Chart IX starting with (S)-malic acid. The (S)-1-methyl-3-pyrrolidinol was shown to be dextrorotatory. As an alternative method of obtaining the resolved isomers of 1-methyl-3-pyrrolidinol, the racemic mixture was treated with (2S,3S)-tartaric acid in methanol. The resulting crystals, after one recrystallization, were converted to the base. This base was the dextrorotatory (S)-1-methyl-3-pyrrolidinol identical to that produced from (S)-malic acid. |
Here is a chemical reaction formula: Reactants are:m1_m5:[H-].[Na+];m2:ClC1=CC=C(C(C(=O)N)=C1)O;m4_m7:BrC1CN(CC1)C;m3:C(C=1C(O)=CC=CC1)(=O)N, Reagents are:m1_m5:CN(C=O)C;m6:CN(C=O)C;m4_m7:CN(C=O)C;m8:O, and Products are 0:O.ClC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C.ClC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cooled suspension of 2.4 g (0.41 mole) sodium hydride in 50 ml of dimethylformamide was added dropwise 17 g (0.1 mole) of 5-chlorosalicylamide dissolved in 50 ml of dimethylformamide at a rate such that the temperature did not exceed 20° C. After addition of the salicylamide was complete, 16.7 g (0.1 mole) of 3-bromo-1-methylpyrrolidine dissolved in 50 ml of dimethylformamide was added dropwise. The reaction mixture was stirred and heated at reflux for 19 hr. The cooled solution was diluted with 250 ml of water and extracted twice with 250 ml portions of chloroform. The chloroform was extracted thrice with 500 ml portions of 3N hydrochloric acid. The aqueous extracts were made alkaline with 50% sodium hydroxide and extracted with ethyl acetate. Drying over magnesium sulfate and evaporation of the ethyl acetate under reduced pressure gave 6 g (23%) of product as a beige solid. The solid was recrystallized from ethyl acetate, m.p. 126°-128° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C1(CCCCC1)N1CC(C1)O;m1_m2_m4_m3:ClC1=C(C(=O)O)C=CC=N1;m1_m2_m4_m3:[H-].[Na+], Reagents are:m1_m2_m4_m3:CN(C=O)C;m5:CN(C=O)C, and Products are 0:C1(CCCCC1)N1CC(C1)OC1=NC=CC=C1C(=O)[O-].[Na+], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 105 g (0.68 mole) of 1-cyclohexyl-3-azetidinol and 106 g (0.68 mole) of 2-chloronicotinic acid in 400 ml of dry dimethylformamide was added at a rapid drop to 52 g (1.35 mole) of 60% sodium hydride/mineral oil suspended in 400 ml of dry dimethylformamide at 60° C. Mild exothermic reaction was noted. After stirring for 2 hr at 60° C., the mixture was filtered. The filter cake was washed with ethylacetate and dried at 80° C./2 mm to give 174 g (86%) of crude title compound. |
Here is a chemical reaction formula: Reactants are:m4_m7:ClC1=NC2=CC=CC=C2C=C1;m5:C(=O)=O;m1_m6_m2_m3:C(C)(C)NC(C)C;m1_m6_m2_m3:C(CCC)[Li];m1_m6_m2_m3:CCCCCC, Reagents are:m4_m7:O1CCCC1;m1_m6_m2_m3:O1CCCC1, and Products are 0:ClC1=NC2=CC=CC=C2C=C1C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 21.3 ml (0.15 mole) of diisopropyl amine in 300 ml of dry tetrahydrofuran under a continuous nitrogen blanket, at -70° C., was added 61.6 ml of 2.7M n-butyllithium in hexane (0.165 mole) while maintaining the temperature at -60° to -70° C. Subsequent to this addition, the temperature was maintained at -65° C. for approximately 20 minutes. A solution of 20 g (0.12 mole) of 2-chloroquinoline in 60 ml of tetrahydrofuran was added dropwise while maintaining the temperature at -60° to -70° C. After holding the temperature at -65° C. for 20 minutes subsequent to this addition, the entire reaction mixture was poured onto a large excess of dry ice. Most of the solvent was evaporated in a stream of air; the residual solvent was removed by rotary evaporation. The residue was taken up in 300 ml water, made basic with dil aq. sodium hydroxide and washed with 3×50 ml of isopropyl ether. The aqueous layer was filtered and made acidic (4 to 5 pH) with dilute aqueous hydrochloric acid. The precipitate was collected, washed with water, isopropyl alcohol, and isopropyl ether, and dried, giving 15.4 g (62%) of white crystals, m.p. 190°-210° C. (decomp.). A sample was recrystallized from isopropyl alcohol giving an analytical sample, m.p. 190°-210° C. (decomp.). |
Here is a chemical reaction formula: Reactants are:m1_m2:OC=1C(=CC=C2C=CC(=NC12)C)C(=O)O;m1_m2:B(F)(F)F;m3:C([O-])(O)=O.[Na+], Reagents are:, and Products are 0:COC(=O)C1=CC=C2C=CC(=NC2=C1O)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 8-Hydroxy-2-methyl-7-quinolinecarboxylic acid (as reported by Meek, W. H. et al., in J. Chem. Eng. Data 1969, 14(3), 388-91) is reacted with methanolic boron trifluoride solution for several hours. The resulting mixture is added to an aqueous solution of sodium bicarbonate to give finally a basic solution. The solution is extracted with chloroform. The chloroform extract is dried over anhydrous sodium sulfate and concentrated and the residue is crystallized from a suitable solvent such as isooctane to give the title compound. |
Here is a chemical reaction formula: Reactants are:m7:Cl;m1_m2_m8:OC1=C(C(=O)O)C=CC=N1;m1_m2_m8:[OH-].[Na+];m4_m5_m9:BrBr;m4_m5_m9:[OH-].[Na+];m3:Br[O-].[Na+];m6:Br[O-].[Na+], Reagents are:m1_m2_m8:O;m4_m5_m9:O, and Products are 0:BrC=1C=C(C(=NC1)O)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 10 g (0.07 mole) of 2-hydroxy-nicotinic acid in 16.8 g of 50% sodium hydroxide (0.21 mole) diluted with 25 ml of water was added 200 ml of sodium hypobromite solution prepared by adding 13.6 g (0.17 mole) of bromine to a solution of 20.16 g of 50% sodium hydroxide (0.25 mole) in 125 ml of water at 0° C. diluted to 400 ml. After 24 hrs of stirring at room temperature, another 100 ml portion of the above sodium hypobromite solution was added and the reaction solution was stirred for another 24 hr. The reaction solution was cooled in an ice bath and acidified carefully with 12N hydrochloric acid. Crystallization from isopropyl alcohol gave 9.7 g (63.5%) of product. A sample was further recrystallized from 95% ethanol, m.p. 245° C. |
Here is a chemical reaction formula: Reactants are:m6:S(C)(=O)(=O)[O-];m2_m8:ClC1=C(C(=O)N)C=C(C=C1)[N+](=O)[O-];m3:CN1CC(CC1)CS(=O)(=O)[O-];m4_m5:CN1CC(CC1)CS(=O)(=O)[O-];m4_m5:[H-].[Na+];m1_m7:[H-].[Na+], Reagents are:m2_m8:CN(C=O)C;m1_m7:CN(C=O)C;m9:CN(C=O)C, and Products are 0:CN1CC(CC1)OC1=C(C(=O)N)C=C(C=C1)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a cooled suspension of sodium hydride (2.42 g of 60% content 0.06 mole) in 50 ml of dimethylformamide under nitrogen was added dropwise a solution of 10 g (0.055 mole) of 2-chloro-5-nitrobenzamide in 20 ml dimethylformamide. The suspension was stirred at room temperature for 1 hr and heated to 60° C. at which time 9.9 g (0.055 mole) of N-methyl-3-pyrrolidinylmesylate (freshly prepared) in 10 ml of dimethylformamide was added. The reaction mixture was heated to 135° C. for 24 hr. Since little product was observed, 9.9 g (0.055 mole) addition N-methyl-3-pyrrolidinylmesylate and 1.21 g (60% in oil, 0.03 mole) of sodium hydride was added. Heating was continued for 24 hr. Another 4 equivalents of the above mesylate was added after cooling the reaction mixture to 100° C. The reaction mixture was maintained at 100° C. for 24 hr. The dimethylformamide was removed by rotary evaporation at 60° C., 0.5 mm Hg. The residue was taken up in 400 ml of methylene chloride and washed with 3×200 ml of 1N sodium hydroxide and 2×200 ml water. The organic layer was extracted with 3×200 ml of 1N hydrochloric acid. The aqueous extracts were combined and washed with ~200 ml chloroform. The aqueous layer was made basic with concentrated sodium hydroxide and extracted with 2×300 ml of methylene chloride. The organic extracts were combined, dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The residue was crystallized from toluene to give 1.7 g (12%) of crude crystals. One recrystallization from toluene afforded light beige crystals, m.p. 215°-10° C. |
Here is a chemical reaction formula: Reactants are:m1_m4:[H-].[Na+];m2_m5:FC=1C=CC(=C(C(=O)N)C1)O;m3:CS(=O)(=O)OC1CN(CC1)C, Reagents are:m1_m4:CN(C=O)C;m2_m5:CN(C=O)C, and Products are 0:FC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 0.44 g (60% in oil, 0.011 mole) of sodium hydride in 10 ml of dimethylformamide was added 1.55 g (0.01 mole) of 5-fluoro-2-hydroxybenzamide in 10 ml of dimethylformamide under nitrogen atmosphere at room temperature. The reaction mixture was heated to 60° C. and 1.80 g (0.01 mole) of 1-methyl-3-pyrrolidinol methane sulfonate (ester) was added. The reaction mixture was then heated to 100° C. for 18 hr. The dimethylformamide was removed by rotary evaporation at 70° C., 0.5 mm Hg. The residue was taken up in 200 ml of methylene chloride, washed with 2×50 ml of 1N sodium hydroxide and 50 ml of water. The organic phase was extracted with 2×50 ml of 1N hydrochloric acid. The combined aqueous extracts were washed with 50 ml of methylene chloride, made basic with concentrated sodium hydroxide and extracted into 2×50 ml of methylene chloride. The combined organic extracts were dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residual oil was crystallized from hexane to give 1.0 g of off-white crystals. m.p. 90°-93° C. |
Here is a chemical reaction formula: Reactants are:m4:S(=O)(Cl)Cl;m1_m5_m2:[OH-].[Na+];m1_m5_m2:ClC1=CC(=C(C(=O)N)C=C1)OC1CN(CC1)C;m3:Cl, Reagents are:m1_m5_m2:O;m6:C(C)(=O)OCC, and Products are 0:ClC1=CC2=C(C(N(CC(O2)CCCl)C)=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 10.4 g (0.26 mole) of sodium hydroxide in 150 ml of water was added 32 g (0.13 mole) of 4-chloro-2-[(1-methyl-3-pyrrolidinyl)oxy]benzamide and the mixture was heated at reflux for 24 hr. The reaction mixture was adjusted to pH 6 with concentrated hydrochloric acid and filtered and the filtrate concentrated. The residue was boiled with 100 ml of isopropyl alcohol and the mixture filtered. The filtrate was concentrated and heated at reflux with 98 g (b 0.83 mole) of thionyl chloride for 1 hr. The excess thionyl chloride was evaporated under reduced pressure. The residue was dissolved in 70 ml of chloroform and the solvent evaporated under reduced pressure. The residue was redissolved in 75 ml of chloroform and 40 ml of triethylamine was added gradually. The mixture was heated at reflux for 1 hr. The solvent was evaporated under reduced pressure to give a dark-brown solid. The solid was dissolved in ethyl acetate and the resulting solution washed twice with 200 ml of water and twice with 250 ml of 20% sodium hydroxide. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure to give 21 g (59%) of dark-brown solid. The solid was recrystallized from isopropyl alcohol to give the title compound, m.p. 85°-87° C. |
Here is a chemical reaction formula: Reactants are:m5:C(C)N(CC)CC;m3:Cl;m1_m6_m2:[OH-].[Na+];m1_m6_m2:BrC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C;m4:S(=O)(Cl)Cl, Reagents are:m1_m6_m2:O, and Products are 0:BrC=1C=CC2=C(C(N(CC(O2)CCCl)C)=O)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 9.6 g (0.24 mole) of sodium hydroxide in 200 ml of water was added 37 g (0.12 mole) of 5-bromo-2-[(1-methyl-3-pyrrolidinyl)oxy]-benzamide and the mixture was heated at reflux for 18 hr. The pH of the mixture was adjusted to 6.7 with concentrated hydrochloric acid solution. The solution was concentrated under reduced pressure and the residue was boiled in 250 ml of isopropyl alcohol for 1 hr. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in chloroform and to the solution was added 28.3 g (0.24 mole) of thionyl chloride. The mixture was heated at reflux for 0.5 hr and cooled to 15° C. with an ice bath. To the mixture was added dropwise 26.6 g (0.26 mole) of triethylamine at such a rate that the temperature did not exceed 25° C. The reaction mixture was stirred at room temperature for 1 hr, then washed consecutively with 3N hydrochloric acid, 15% aqueous sodium hydroxide and water. The chloroform layer was dried over magnesium sulfate and concentrated under reduced pressure to give 23 g (60%) of brown solid. A portion of the solid was recrystallized from ethyl acetate-isopropyl ether, m.p. 92°-94° C. |
Here is a chemical reaction formula: Reactants are:m1_m8_m2:[OH-].[Na+];m1_m8_m2:COC=1C=CC(=C(C(=O)N)C1)OC1CN(CC1)C;m5:C(C)N(CC)CC;m4:S(=O)(Cl)Cl;m3:Cl;m7:[OH-].[Na+];m6:Cl, Reagents are:m1_m8_m2:O;m10:O;m9:O;m11:O, and Products are 0:ClCCC1OC2=C(C(N(C1)C)=O)C=C(C=C2)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 19.2 g (0.48 mole) of sodium hydroxide in 500 ml of water was added 60 g (0.24 mole) of 5-methoxy-2-[(1-methyl-3-pyrrolidinyl)oxy]-benzamide and the mixture was heated at reflux for 24 hr. The reaction mixture was cooled and the pH adjusted to 6.8 with concentrated hydrochloric acid. The mixture was concentrated under reduced pressure and the residue was boiled in isopropyl alcohol for 1 hour. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in 500 ml of chloroform and to this solution was added 114 g (0.96 mole) of thionyl chloride. The mixture was heated at reflux for 48 hr, then cooled with an ice/acetone bath. To the mixture was added dropwise 97 g (0.96 mole) of triethylamine at such a rate that the temperature did not exceed 25° C. The reaction solution was washeed in sequence with water, 3N hydrochloric acid solution, water, 15% aqueous sodium hydroxide and water and finally dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give a black solid. The solid was purified on a silica gel column using ethyl acetate as the eluting solvent to give on isolation 15 g (23%) of beige colored product, m.p. 98°-100° C. |
Here is a chemical reaction formula: Reactants are:m1_m4:ClC1=CC2=C(C(N(CC(O2)CCCl)C)=O)C=C1;m2_m3:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3;m2_m3:[S-2].[K+].[K+], Reagents are:m1_m4:C1(=CC=CC=C1)C, and Products are 0:ClC1=CC2=C(C(N(CC(O2)CCCl)C)=S)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 43 g (0.16 mole) of 8-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one in 400 ml of dry toluene was added a mixture of 23 g (0.12 mole) of phosphorus pentasulfide and 23 g of potassium sulfide which had been ground together. The reaction mixture was stirred and heated at reflux for 24 hr. The mixture was filtered hot and the filtrate concentrated under reduced pressure to give 25.5 g (55%) of orange oil which solidified on standing at room temperature. The solid was recrystallized from ethanol, m.p. 105°-106° C. |
Here is a chemical reaction formula: Reactants are:m1_m4:BrC=1C=CC2=C(C(N(CC(O2)CCCl)C)=O)C1;m2_m3:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3;m2_m3:[S-2].[K+].[K+], Reagents are:m1_m4:C1(=CC=CC=C1)C, and Products are 0:BrC=1C=CC2=C(C(N(CC(O2)CCCl)C)=S)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 11.0 g (0.035 mole) of 7-bromo-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one in 150 ml of dry toluene was added a mixture of 13.4 g (0.07 mole) of phosphorus pentasulfide and 13.4 g of potassium sulfide which had been ground together. The reaction mixture was heated at reflux for 5 hr under a nitrogen atmosphere. The mixture was filtered hot and the filtrate concentrated under reduced pressure. The residue was dissolved in chloroform. The chloroform solution was washed twice with dilute aqueous sodium hydroxide, dried over magnesium sulfate and concentrated under reduced pressure to give 8.5 g (72%) of yellow solid. The solid was recrystallized from ethanol, m.p. 118°-120° C. |
Here is a chemical reaction formula: Reactants are:m1_m2:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3;m1_m2:[S-2].[K+].[K+];m3_m4:ClCCC1OC2=C(C(N(C1)C)=O)C=CC1=CC=CC=C12, Reagents are:m3_m4:C1(=CC=CC=C1)C, and Products are 0:ClCCC1OC2=C(C(N(C1)C)=S)C=CC1=CC=CC=C12, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 9.55 g of phosphorus pentasulfide and 9.5 g of potassium sulfide were ground together and added to a solution of 20.2 g (0.07 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylnaphth[2,1-f][1,4]oxazepin-5(4H)-one in 200 ml of dry toluene. The mixture was stirred and heated at reflux for 7 hr. The hot reaction mixture was filtered and the product crystallized from the cooled filtrate. Recrystallization from chloroform gave 18 g (84%) of yellow crystals, m.p. 167°-170° C. |
Here is a chemical reaction formula: Reactants are:m2_m3:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3;m2_m3:[S-2].[K+].[K+];m1_m4:ClC=1C=CC2=C(C(N(CC(O2)CCCl)C)=O)C1, Reagents are:m1_m4:C1(=CC=CC=C1)C, and Products are 0:ClC=1C=CC2=C(C(N(CC(O2)CCCl)C)=S)C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 20 g (0.07 mole) of 7-chloro-2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-benzoxazepin-5(4H)-one in 200 ml of toluene was added a mixture of 9.55 g (0.05 mole) of phosphorus pentasulfide and 9.5 g of potassium sulfide which had been ground together. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to give a yellow solid. Recrystallization from absolute ethanol gave 12.5 g (68%) of the product, m.p. 102°-104° C. |
Here is a chemical reaction formula: Reactants are:m1_m4:ClCCC1OC2=C(C(N(C1)C)=O)C=C(C=C2)OC;m2_m3:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3;m2_m3:[S-2].[K+].[K+], Reagents are:m1_m4:C(Cl)(Cl)Cl, and Products are 0:ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 10.3 g (0.04 mole) of 2-(2-chloroethyl)-2,3-dihydro-7-methoxy-4-methyl-1,4-benzoxazepin-5(4H)-one in 200 ml of chloroform was added a mixture of 5.7 g (0.03 mole) of phosphorus pentasulfide and 5.7 g of potassium sulfide which had been ground together. The reaction mixture was stirred and heated at reflux under nitrogen atmosphere for 5 hr. The mixture was filtered hot and the filtrate concentrated under reduced pressure. The residue, an orange solid, was recrystallized from ethanol to give 7.4 g (65%) of product, m.p. 98°-100° C. |
Here is a chemical reaction formula: Reactants are:m1_m3:Cl.ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2;m2:S(=O)(=O)(Cl)Cl, Reagents are:m1_m3:CN(C=O)C, and Products are 0:ClC1=CC=2C(N(CC(OC2N=C1)CCCl)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A sample of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5-(4H)-one hydrochloride (10 g, 136 mole) was dissolved in dimethylformamide (150 ml) and heated to reflux. Sulfuryl chloride (20 g, 0.148 mole) was then added dropwise over a period of 40-50 minutes. The reaction was allowed to stir at reflux for 30 minutes following the addition of SO2CL2. After cooling, the contents of the flask were partitioned between water (150 ml) and benzene (150 ml). The benzene layer was saved and the water layer extracted with an additional amount of benzene (2×50 ml). The benzene extracts were combined and washed with dilute aqueous potassium hydroxide (2×50 ml) followed by dilute aqueous hydrochloric acid (2×50 ml). The benzene layer was dried over sodium sulfate and concentrated by rotary evaporation (~70° C., water aspirator) yielding 2.61 g of crude material. The crude material was recrystallized from isopropyl ether giving 1.25 g (12.6%) of off-white crystals, m.p. 78°-79° C. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2;m1_m3_m2:C1(C=2C(C(N1)=O)=CC=CC2)=O.[K], Reagents are:m1_m3_m2:CN(C=O)C, and Products are 0:O=C1N(C(C2=CC=CC=C12)=O)CCC1OC2=C(C(N(C1)C)=O)C=CC=N2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 4.92 g (0.02 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f]-1,4-oxazepin-5-(4H)one in 35 ml of dimethylformamide was added 7.55 g (0.041 mole) of potassium phthalimide. The mixture was stirred for 5 hr at 100° C. and left standing at room temperature overnight. Dimethylformamide was removed by rotary evaporation (80° C. vacuum pump). The residue was taken up in 100 ml of chloroform and washed with water (2×30 ml) and 2M potassium hydroxide (2×3 ml). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation (70° C., water aspirator). The 6.26 g of crude product was recrystallized from isopropyl alcohol to give 2.60 g (36%) white crystalline powder, m.p. 146°-47° C. |
Here is a chemical reaction formula: Reactants are:m3:COC1=CC=C(C=C1)P1(SP(S1)(C1=CC=C(C=C1)OC)=S)=S;m1_m4_m2:CN1CC(OC2=C(C1=O)C=CC=N2)CCC#N;m1_m4_m2:COC1=CC=C(C=C1)P1(SP(S1)(C1=CC=C(C=C1)OC)=S)=S, Reagents are:m1_m4_m2:C1(=CC=CC=C1)C, and Products are 0:CN1CC(OC2=C(C1=S)C=CC=N2)CCC#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 11.0 g (0.04 mole) of 2,3,4,5-tetrahydro-4-methyl-5-oxopyrido[3,2-f][1,4]-oxazepine-2-propanenitrile in 175 ml toluene was added 10.5 g (0.026 mole) of 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide. The reaction mixture was heated to reflux for 2 hr with vigorous mechanical stirring. Another 3.0 g (0.007 mole) of 2,4 bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide was added and heating continued for 1 hr additional. The reaction mixture was allowed to cool and stand overnight at room temperature. Toluene was removed by rotary evaporation (90° C., water aspirator) and the residue taken up in 200 ml chloroform. This was washed with 2×50 ml 2M aqueous potassium hydroxide and concentrated by rotary evaporator (90° C., water aspirator). Crystallization ensued upon cooling. Recrystallization from isopropyl alcohol afforded 1.60 g (13.8%) product, m.p. 155°-56° C. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:ClCCC1OC=2C(=NC=3C=CC=CC3C2)C(N(C1)C)=O;m1_m3_m2:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3, Reagents are:m1_m3_m2:C(C)#N;m4:C1(=CC=CC=C1)C, and Products are 0:ClCCC1OC=2C(=NC=3C=CC=CC3C2)C(N(C1)C)=S, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 3.0 g (0.01 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[6,7-b]-quinolin-5(4H)-one in 30 ml of acetonitrile was added 1.3 g (0.006 mole) of phosphorus pentasulfide. The mixture was stirred vigorously at reflux for 2 hr. After cooling, the reaction mixture was diluted with 60 ml of toluene and filtered. The residue on the filter paper was washed with 50 ml of additional toluene/acetonitrile, 3/1, V/V. The filtrate was washed with 3×50 ml saturated sodium carbonate (caution: gas evolved), dried over anhydrous sodium sulfate, filtered, treated with activated charcoal, filtered again and concentrated by rotary evaporation (90° C., 30 mm). The residual syrup was crystallized from isopropyl alcohol, yielding 1.6 g (52%) of yellow crystals, m.p. 114°-116° C. |
Here is a chemical reaction formula: Reactants are:m3_m4_m10:CN1CC(CC1)O;m3_m4_m10:ClC=1C=NC=C(C1C(=O)O)Cl;m5_m8:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m5_m8:C(Cl)(Cl)(Cl)Cl;m6_m7:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m6_m7:C(Cl)(Cl)(Cl)Cl;m2_m9:[H-].[Na+], Reagents are:m3_m4_m10:CN(C=O)C;m11:C(C)N(CC)CC;m2_m9:CN(C=O)C, and Products are 0:ClC1=CN=CC2=C1CN(CC(O2)CCCl)C;0:C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a suspension of 2.1 g (60% in oil, 0.052 mole) of sodium hydride in 125 ml of dimethylformamide heated to 60° C. under a nitrogen gas blanket was added a solution of 2.65 g (0.026 mole) of N-methyl-3-pyrrolidinol and 5.0 g (0.026 mole) of 3,5-dichloropyridine-4-carboxylic acid in 40 ml of dimethylformamide dropwise at such a rate as to maintain 60° C. Subsequent to this addition, the mixture was heated to 75° C. for 3 hr. The solvent was then removed by rotary evaporation (60° C., 5 mm). The entire solid residue was suspended in 150 ml methylene chloride and hydrogen chloride added until a pH of 3 was reached. To the resulting mixture was added 15 g (0.057 mole) of triphenylphosphine and 15 g carbon tetrachloride and the entire mixture heated to reflux. After 1 hr, 7.5 g (0.029 mole) of triphenylphosphine and 7.5 g carbon tetrachloride were added, followed by the same increments 1 hr later. The reaction was driven to completion by adding 20 ml of triethylamine. The reaction mixture was washed with 6×50 ml of 3N hydrochloric acid, dried over sodium sulfate, filtered and concentrated by rotary evaporation. To the residue was added ethyl acetate, which caused much tarry material to fall out of solution, leaving the desired product and triphenylphosphine oxide in solution. The mixture was chromatographed by column chromatography using silica gel as the stationary phase and ethyl acetate as eluent. Similar fractions were combined and ethyl acetate removed by rotary evaporation, yielding 0.6 g (7%), of white crystals, m.p. 134°-38° C. |
Here is a chemical reaction formula: Reactants are:m3:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3;m1_m4_m2:ClCCC1OC2=C(C(N(C1)C)=O)C=C(C=C2)[N+](=O)[O-];m1_m4_m2:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3, Reagents are:m1_m4_m2:C(C)#N;m5:C1(=CC=CC=C1)C, and Products are 0:ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 2.0 g (0.007 mole) of 2-(2-chloroethyl)-2,3-dihydro-4-methyl-7-nitro-1,4-benzoxazepin-5(4H)-one in 35 ml of acetonitrile was added 1.0 g (0.0023 mole) of phosphorus pentasulfide and the mixture heated to reflux for 2 hr. Another 0.4 g (0.001 mole) of phosphorus pentasulfide was added and heating continued for 2 hr. After cooling, the reaction mixture was diluted with 100 ml of toluene and filtered. The filtrate was washed with 3×50 ml of saturated sodium bicarbonate and 100 ml of water, dried over sodium sulfate, filtered, charcoaled, filtered, and concentrated by rotary evaporation. The crude oil was crystallized from isopropyl ether/toluene to give 1.2 g (57%) of yellow crystals, m.p. 153°-155° C. |
Here is a chemical reaction formula: Reactants are:m3:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3;m1_m4_m2:ClCCC1OC2=C(C(N(C1)C)=O)C=C(C=C2)F;m1_m4_m2:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3, Reagents are:m1_m4_m2:C(C)#N;m5:C1(=CC=CC=C1)C, and Products are 0:ClCCC1OC2=C(C(N(C1)C)=S)C=C(C=C2)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 1.0 g (0.0039 mole) of 2-(2-chloroethyl)-2,3-dihydro-7-fluoro-4-methyl-1,4-benzoxazepin-5(4H)-one in 30 ml of acetonitrile was added 0.7 g (0.0016 mole) of phosphorus pentasulfide and the reaction mixture heated to reflux. After 2 hr, another 0.4 g (0.009 mole) of phosphorus pentasulfide was added and heating continued for 2 hr. The reaction mixture was diluted with 70 ml of toluene and filtered. The filtrate was washed carefully with 3×50 ml of saturated sodium bicarbonate and 50 ml of water, dried over sodium sulfate, filtered, charcoaled, filtered and concentrated by rotary evaporation. The crude material was recrystallized from diisopropyl ether to give 0.55 g (52%) of yellow crystals, m.p. 135°-137° C. |
Here is a chemical reaction formula: Reactants are:m2:CNC;m1:C(C1=CC=CC=C1)N1CC(OC2=C(C1=O)C=CC=C2)CCCl, Reagents are:, and Products are 0:O.C(C1=CC=CC=C1)N1CC(OC2=C(C1=O)C=CC=C2)CCN(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Following the procedure of Example 1, 4-benzyl-2-(2-chloroethyl)-2,3-dihydro-1,4-benzoxazepin-5(4H)-one and dimethylamine were reacted and the free base of the title compound was obtained in the concentrated residue. Recrystallization from ethanol-water gave the product, m.p. 75°-77° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:ClCCC1OC2=C(C(N(C1)C)=S)C=CC=N2;m1_m2_m3:C(C)NCC, Reagents are:m1_m2_m3:C(C)O, and Products are 0:C(C)N(CCC1OC2=C(C(N(C1)C)=S)C=CC=N2)CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 2-(2-Chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepine-5(4H)-thione and diethylamine in ethanol are heated together to obtain the title compound. |
Here is a chemical reaction formula: Reactants are:m1:ClCC1OC2=C(C(N(C1)C)=O)C=CC=N2;m2:ClCCC1OC2=C(C(N(C1)C)=O)C=CC=N2, Reagents are:, and Products are 0:CN(C)CC1OC2=C(C(N(C1)C)=O)C=CC=N2, please give me the reaction condition of this formula. | The condition of this chemical reaction is: When in the procedure of Example 10, 2-chloromethyl-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one is substituted for 2-(2-chloroethyl)-2,3-dihydro-4-methylpyrido[3,2-f][1,4]-oxazepin-5(4H)-one, the title compound is prepared and is isolated if desired as a pharmaceutically acceptable salt. |