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Here is a chemical reaction formula: Reactants are:m1_m2_m4:NCCP(OCC)(OCC)=O;m1_m2_m4:C(C)N(CC)CC;m3:Cl.C(C1=CN=CC=C1)(=O)Cl, Reagents are:m1_m2_m4:ClCCl, and Products are 0:C(C)OP(=O)(OCC)CCNC(=O)C=1C=NC=CC1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of diethyl 2-aminoethylphosphonate (8.1 g), triethylamine (9.1 g) and dichloromethane (100 ml) at 5° C. was added nicotinic acid chloride hydrochloride (10.4 g) in small portions over a period of 15 minutes. After being stirred for additional 1.5 hours, the reaction mixture was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (10% methanol in chloroform) to give 11.2 g of N-(2-diethoxyphosphoryl-ethyl)-3-pyridinecarboxamide as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:NCCP(OCC)(OCC)=O;m1_m2_m3_m4_m5:C(C1=CC=NC=C1)(=O)O;m1_m2_m3_m4_m5:ON1N=NC2=C1C=CC=C2;m1_m2_m3_m4_m5:Cl.C(C)N=C=NCCCN(C)C, Reagents are:m1_m2_m3_m4_m5:ClCCl, and Products are 0:C(C)OP(=O)(OCC)CCNC(=O)C1=CC=NC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of diethyl 2-aminoethylphosphonate (12.5 g), isonicotinic acid (10.2 g), 1-hydroxybenzotriazole (11.2 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (15.83 g) and dichloromethane (190 ml) was stirred at room temperature for 15 hours. The reaction mixture was washed with aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (5% methanol-chloroform) to give 7.94 g of N-(2-diethoxyphosphorylethyl)-4-pyridinecarboxamide as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5_m3:NCCP(OCC)(OCC)=O;m1_m2_m5_m3:C(C)N(CC)CC;m1_m2_m5_m3:C(C)(=O)OC(C)=O;m4:C([O-])([O-])=O.[K+].[K+], Reagents are:m1_m2_m5_m3:ClCCl;m6:[Cl-].[Na+].O, and Products are 0:C(C)(=O)NCCP(OCC)(OCC)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of diethyl 2-aminoethylphosphonate (10.5 g), triethylamine (7.0 g) in dichloromethane (200 ml) at 0° C. was added dropwise acetic anhydride (7.1 g). After 20 hours at room temperature, the reaction mixture was diluted with brine, made basic with 5% aqueous potassium carbonate, and extracted twice with dichloromethane. The extract was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (5% methanol in chloroform) to give (12.1 g) of diethyl 2-acetylaminoethylphosphonate as an oil. |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m5_m2_m3:C[O-].[Na+];m1_m5_m2_m3:C(C)OC(C(P(=O)(O)O)(CC)CC)=O;m1_m5_m2_m3:C(C)/C(/C=O)=C\CC, Reagents are:m1_m5_m2_m3:CO, and Products are 0:C(C)/C(/C=C/C(=O)OC)=C\CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a 28 wt % solution of sodium methoxide in methanol (25.7 g) at 10° C. were added dropwise diethyl phosphonoacetic acid ethyl ester (25.3 g) and (E)-2-ethyl-2-pentenal (11.5 g) successively under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 3 hours, poured into chilled water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (dichloromethane) to give 13.4 g of methyl (E,E)-4-ethyl-2,4-heptadienoate as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C(C)/C(/C=C/CO)=C\CC;m1_m3_m2:C(C)(=O)OC(C)=O, Reagents are:m1_m3_m2:N1=CC=CC=C1, and Products are 0:C(C)(=O)OC\C=C\C(=C\CC)\CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of (E,E)-4-ethyl-2,4-heptadien-1-ol (10.1 g) in pyridine (29 g) at 0° C. was added dropwise acetic anhydride (22.2 g). After two hours at room temperature, the reaction mixture was evaporated in vacuo. The residue was diluted with ethyl acetate, washed with 0.5N hydrochloric acid and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (5% ethyl acetate in hexane) to give (E,E)-1-acetoxy-4-ethyl-2,4-heptadiene (9.75 g) as an oil. |
Here is a chemical reaction formula: Reactants are:m4_m6:C(C)C(C=CCN)=CC;m1_m2_m3_m5:CC1=NC=CC=C1C(=O)O;m1_m2_m3_m5:Cl.C(C)N=C=NCCCN(C)C;m1_m2_m3_m5:ON1N=NC2=C1C=CC=C2, Reagents are:m4_m6:ClCCl;m1_m2_m3_m5:ClCCl;m7:C(O)([O-])=O.[Na+], and Products are 0:CC1=NC=CC=C1C(=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 2-methyl-3-pyridinecarboxylic acid (1.66 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.12 g), and N-hydroxybenzotriazole (1.63 g) in dichloromethane (25 ml) was stirred at 0° C. for 15 minutes. A solution of 4-ethyl-2,4-hexadien-1-ylamine (1.26 g) in dichloromethane (6.3 ml) was added dropwise to the solution over a period of 10 minutes. The mixture was stirred at 0° C. for 30 minutes and then at room temperature for 3 hours. The reaction mixture was diluted with aqueous sodium hydrogen carbonate. The organic phase separated was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (4% methanol-chloroform) to give N-[(2E,4E)- and (2Z,4E)-4-ethyl-2,4-hexadien-1-yl]-2-methyl-3-pyridinecarboxamide 2.38 g) as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m7:N1=CC(=CC2=CC=CC=C12)C(=O)O;m1_m2_m3_m7:Cl.C(C)N=C=NCCCN(C)C;m1_m2_m3_m7:ON1N=NC2=C1C=CC=C2;m4_m5:C(C)C(C=CCN)=CC, Reagents are:m6:C(O)([O-])=O.[Na+];m8:C(C)N(CC)CC;m1_m2_m3_m7:ClCCl;m4_m5:ClCCl, and Products are 0:N1=CC(=CC2=CC=CC=C12)C(=O)N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 3-quinolinecarboxylic acid (3.32 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.37 g), N-hydroxybenzotriazole (2.6 g) and dichloromethane (50 ml) at 0° C. was added triethylamine (2.3 ml). After 15 minutes, a solution of 4-ethyl-2,4-hexadien-1-ylamine (2.0 g) in dichloromethane (10 ml) was added dropwise to the solution over a period of 10 minutes. The mixture was stirred at 0° C. for 30 minutes and then at room temperature overnight. The reaction mixture was diluted with aqueous sodium hydrogen carbonate. The separated organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (1% methanol-chloroform) to give N-[(2E,4E)- and (2Z,4E)-4-ethyl-2,4-hexadien-1-yl]-3-quinolinecarboxamide (3.18 g) as an oil. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m5:NC1=CC=C(C=N1)C(=O)O;m1_m2_m3_m5:ON1N=NC2=C1C=CC=C2;m1_m2_m3_m5:Cl.C(C)N=C=NCCCN(C)C;m4_m6:C(C)C(C=CCN)=CC, Reagents are:m7:CN(C1=CC=NC=C1)C;m8:C(O)([O-])=O.[Na+];m1_m2_m3_m5:CN(C=O)C;m4_m6:CN(C=O)C, and Products are 0:C(C)C(C=CCNC(=O)C=1C=NC(=CC1)N)=CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 6-aminopyridine-3-carboxylic acid (4.24 g), N-hydroxybenzotriazole (5.13 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (6.44 g) in N,N-dimethylformamide (100 ml) was stirred at 0° C. for 10 minutes. A solution of 4-ethyl-2,4-hexadien-1-ylamine (4.24 g) in N,N-dimethylformamide (50 ml) was added dropwise to the mixture over a period of 10 minutes and 4-dimethylaminopyridine (4.0 g) was added to the mixture. The mixture was stirred at 0° C. for 2 hours and then at room temperature overnight. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted three times with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (4% methanol-chloroform) to give N-(4-ethyl-2,4-hexadien-1-yl)-6-amino-3-pyridinecarboxamide (5.7 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)C(C=CCNC(=O)C=1C=NC(=CC1)N)=CC;m1_m2_m3:CS(=O)(=O)Cl, Reagents are:m1_m2_m3:N1=CC=CC=C1, and Products are 0:C(C)C(C=CCNC(=O)C=1C=NC(=CC1)NS(=O)(=O)C)=CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of N-(4-ethyl-2,4-hexadien-1-yl)-6-amino-3-pyridinecarboxamide (3.0 g) and methanesulfonyl chloride (1.54 g) in pyridine (25 ml) was stirred at 50° C. for 3 hours. The reaction mixture was evaporated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed with 0.5N hydrochloric acid and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (3% methanol-chloroform) to give N-(4-ethyl-2,4-hexadien-1-yl)-6-methansulfonamido-3-pyridinecarboxamide. |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m5_m2:C[O-].[Na+];m1_m5_m2:C(C)OC(C(P(=O)(O)O)(CC)CC)=O;m3_m6:C/C(/C=O)=C\CC, Reagents are:m1_m5_m2:CO;m3_m6:O1CCCC1, and Products are 0:C/C(/C=C/C(=O)OC)=C\CC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a 28 wt % solution of sodium methoxide in methanol (226 g) at 20° C. was added dropwise diethyl phosphonoacetic acid ethyl ester (239.8 g). The solution was stirred at the same temperature for 30 minutes under a nitrogen atmosphere. A solution of (E)-2-methyl-2-pentenal (100 g) in tetrahydrofuran (200 ml) was added dropwise at 20° C. during 20 minutes and the solution was stirred for 1 hour. The reaction mixture was poured into chilled water and extracted twice with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo to give methyl (E,E)-4-methyl-2,4-heptadienoate (169.2 g) as an oil. This oil was used in the next reaction without further purification. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C/C(/C=C/CO)=C\CC;m1_m3_m2:C(C)(=O)OC(C)=O, Reagents are:m1_m3_m2:N1=CC=CC=C1, and Products are 0:C(C)(=O)OC\C=C\C(=C\CC)\C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of (E,E)-4-methyl-2,4-heptadien-1-ol (106 g) in pyridine (333 g) at 0° C. was added dropwise acetic anhydride (258 g). After two hours at room temperature, the reaction mixture was evaporated in vacuo. The residue was diluted with ethyl acetate, washed with 0.5N-hydrochloric acid and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was distilled to give (E,E)-1-acetoxy-4-methyl-2,4-heptadiene (117.65 g) as an oil. |
Here is a chemical reaction formula: Reactants are:m4:O;m1_m5_m2_m3:C[O-].[Na+];m1_m5_m2_m3:C(C)OC(C(P(=O)(O)O)(CC)CC)=O;m1_m5_m2_m3:C/C(/C=O)=C\CCC, Reagents are:m1_m5_m2_m3:CO, and Products are 0:C/C(/C=C/C(=O)OC)=C\CCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a 28 wt % solution of sodium methoxide in methanol (112.6 g) at 10° C. were added dropwise diethyl phosphonoacetic acid ethyl ester (110.75 g) and (E)-2-methyl-2-hexenal (50.36 g) successively under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 4 hours, poured into chilled water and extracted with dichloromethane. The extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated to give 74.88 g of crude methyl (E,E)-4-methyl-2,4-octadienoate as an oil. This oil was used in the next reaction without further purification. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:C(C)C(=CC(CNC(=O)C=1C=NC=CC1)=NO)C(C)[N+](=O)[O-];m1_m2_m3_m4:ClC1=CC(=CC=C1)C(=O)OO;m1_m2_m3_m4:C(Cl)(Cl)Cl, Reagents are:m1_m2_m3_m4:CC(=O)C, and Products are 0:C(C)C(=CC(CNC(=O)C=1C=[N+](C=CC1)[O-])=NO)C(C)[N+](=O)[O-], please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-3-pyridinecarboxamide (306 mg), 3-chloroperbenzoic acid (323 mg), chloroform (15 ml) and acetone (40 ml) was stirred at room temperature for 10 hours. The resulting precipitates were collected and washed with acetone to give N-(4-ethyl-2-hydroxyimino-5-nitro-3-hexen-1-yl)-3-pyridinecarboxamide 1-oxide. |
Here is a chemical reaction formula: Reactants are:m4:N;m5:C1CC(NC2CCC3=C(C12)C=CC=C3)=O;m3:C(C)N;m2:C1(=CC=CC=C1)CC(=O)O, Reagents are:m6:C(CO)O, and Products are 0:C(C)N1C(CCC2(C3=C(CC=C12)C=CC=C3)C)=O;0:C(C)N1C(CC[C@]2(C3=C(CC[C@H]12)C=CC=C3)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: By following the procedures described in Example 40, Steps A, B, C, D, E and F using phenylacetic acid as the starting material and using ethylamine rather than ammonia, and digylme rather ethylene glycol in Step F, the compound 4-ethyl-10b-methyl-1,2,3,4,6,10b-hexahydrobenzo[f]quinolin-3one was prepared. This hexahydrobenzo[f]quinolin-3-one was hydrogenated by following the procedures described Example 22 except that the reaction was carried out at 70° C. over 7 hours to afford a crude reaction mixture. The reaction mixture was filtered and the solvents evaporated under vacuum to afford a glassy solid residue. The crude product was purified by chromatography on SiO2 (gradient elution from 100% hexanes to 100% CHCl3) to afford 92 mg of the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m5:C1CC(NC2CCC3=C(C12)C=CC=C3)=O;m2:C1(=CC=CC=C1)CC(=O)O;m4:N;m3:C(CCC)N, Reagents are:m7:C(OC)COC;m6:C(CO)O, and Products are 0:C(CCC)N1C(CCC2(C3=C(CC=C12)C=CC=C3)C)=O;0:C(CCC)N1C(CC[C@]2(C3=C(CC[C@H]12)C=CC=C3)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: By following the procedures described in Example 40, Steps A, B, C, D, E and F using phenylacetic acid as the starting material and in Step F using n-butylamine rather than ammonia and dimethoxyethane rather than ethylene glycol, the compound 4-n-butyl-10b-methyl-1,2,3,4,6,10b-hexahydrobenzo[f]quinolin-3-one was prepared. This hexahydrobenzo[f]quinolin-3-one was hydrogenated by following the procedures described Example 22 except that the reaction was carried out at 60° C. over 7 hours and worked up according to the procedures described in Example 42 to afford 61 mg of the title compound as a colorless oil. |
Here is a chemical reaction formula: Reactants are:m3:CN;m2:C1(=CC=CC=C1)CC(=O)O;m4:N;m5:C1CC(NC2CCC3=C(C12)C=CC=C3)=O, Reagents are:m6:C(CO)O;m7:COCCOCCOC, and Products are 0:CN1C(CCC2(C3=C(CC=C12)C=CC=C3)C)=O;0:CN1C(CC[C@]2(C3=C(CC[C@H]12)C=CC=C3)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: By following the procedures described in Example 40, Steps A, B, C, D, E and F using phenylacetic acid as the starting material and in Step F using methylamine rather than ammonia and diglyme rather than ethylene glycol, the compound 4-methyl-10b-methyl-1,2,3,4,6,10b-hexahydrobenzo[f]quinolin-3-one was prepared. This hexahydrobenzo[f]quinolin-3-one was hydrogenated by following the procedures described in Example 22 except that the reaction was carried out at 60° C. over 7 hours. The reaction mixture was filtered and solvent evaporated under vacuum. The residue was purified by chromatography on SiO2 (CHCl3 as eluent) followed by recrystaliization from ethyl acetate/hexanes to afford 154 mg of the title compound. Melting point 111°-113° C. |
Here is a chemical reaction formula: Reactants are:m3:CN;m2:ClC1=CC=C(C=C1)CC(=O)O;m4:N;m5:C1CC(NC2CCC3=C(C12)C=CC=C3)=O, Reagents are:m6:C(CO)O;m7:CC(C)O, and Products are 0:CN1C(CC[C@@]2(C3=C(CC=C12)C=C(C=C3)Cl)C)=O;0:CN1C(CC[C@@]2(C3=C(CC[C@@H]12)C=C(C=C3)Cl)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: By following the procedures described in Example 40, Steps A, B, C, D, E and F using p-chlorophenylacetic acid as the starting material and in Step F using methylamine rather than ammonia and 2-propanol rather than ethylene glycol, the compound (R)(+)-4-methyl-8-chloro-10b-methyl-1,2,3,4,6,10b-hexahydro-benzo[f]quinolin-3-one was prepared. This hexahydrobenzo[f]quinolin-3-one was reduced according to the procedure described in Example 40, Step G. The crude product was purified by chromatography on SiO2 (ethyl acetate as eluent) to afford 5.6 g of the title compound as a pale oil which solidified on standing. Melting point 60°-61° C. |
Here is a chemical reaction formula: Reactants are:m3_m2_m1:FC1=C(C(=CC=C1[N+](=O)[O-])F)C, Reagents are:m3_m2_m1:[Pd];m3_m2_m1:C(C)(=O)O, and Products are 0:FC1=C(N)C=CC(=C1C)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To acetic acid (1.2 l) are added 5% Pd-C (24 g) and 2,6-difluoro-3-nitrotoluene (238.7 g) and the mixture is subjected to catalytic reduction at room temperature under 4.5 atoms. The 5% Pd-C is filtered off and the acetic acid is distilled off under reduced pressure. The residue is poured into ice-water, neutralized, extracted with dichloromethane, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the residue is distilled under reduced pressure to give 2,4-difluoro-3-methylaniline (138 g), colorless oils, b.p.: 75° C./11 mmHg. |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:FC1=C(N)C=CC(=C1C)F;m1_m2_m5:F[B-](F)(F)F.[H+];m3_m4:N(=O)[O-].[Na+], Reagents are:m1_m2_m5:O;m3_m4:O, and Products are 0:F[B-](F)(F)F.FC1=C(C=CC(=C1C)F)[N+]#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 2,4-difluoro-3-methylaniline (20 g) are added 42% tetrafluoroboric acid (56 ml) and water (28 ml) under ice cooling and thereto a solution of sodium nitrite (10 g) in water (20 ml) is added dropwise at below 10° C. After dropwise addition, the mixture is stirred at 0° C. for 15 minutes and the formed crystals are filtered, which is washed with a mixture of ethanol--diethyl ether (1:2), then with diethyl ether, followed by drying under reduced pressure to give 2,4-difluoro-3-methylbenzene diazonium tetrafluoroborate (28.95 g), m.p. 114°-115° C. |
Here is a chemical reaction formula: Reactants are:m3_m2_m1:FC1=C(C(=C(C=C1F)[N+](=O)[O-])F)C, Reagents are:m3_m2_m1:[Pd];m3_m2_m1:C(C)(=O)O, and Products are 0:FC1=C(N)C=C(C(=C1C)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To acetic acid (350 ml) are added 5% Pd-C (3.5 g) and 2,3,6-trifluoro-5-nitrotoluene (35 g) and the mixture is subjected to catalytic reduction at room temperature under atomospheric pressure. 5% Pd-C is filtered off and the acetic acid is distilled off under reduced pressure. The residue is poured into ice-water, neutralized, extracted with dichloromethane, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the obtained residue is distilled under reduced pressure to give 2,4,5-trifluoro-3-methylaniline (22.86 g), as yellow crystals, b.p. 85° C./20 mmHg. |
Here is a chemical reaction formula: Reactants are:m3:ClN1C(CCC1=O)=O;m4:[OH-].[Na+];m6_m1_m2:FC1=C(N)C=C(C(=C1C)F)F;m6_m1_m2:CSC, Reagents are:m6_m1_m2:ClCCl;m5:C(C)N(CC)CC, and Products are 0:FC1=C(N)C(=C(C(=C1C)F)F)CSC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To anhydrous dichloromethane (170 ml) are added 2,4,5-trifluoro-3-methylaniline (16.89 g) and dimethyl sulfide (11 ml). Thereto N-chlorosuccinimide (17.2 g) is added gradually below 5° C. After stirring for 30 minutes, triethylamine (21 ml) is added dropwise and the mixture is refluxed over night. After the mixture is cooled and made alkaline with 5% aqueous sodium hydroxide solution, the resultant is extracted with dichloromethane, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the residue is purified by silica-gel column-chromatography (dichloromethane : n-hexane =1 : 1) to give 2,4,5-trifluoro-3-methyl-6-methylthiomethylaniline (8.3 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m6_m3_m5:FC1=C(C(=C(C(=C1F)C)[N+](=O)[O-])F)C;m1_m2_m6_m3_m5:COCCO;m1_m2_m6_m3_m5:CN1CCNCC1, Reagents are:m4:O;m1_m2_m6_m3_m5:C(C)N(CC)CC;m1_m2_m6_m3_m5:O, and Products are 0:CN1CCN(CC1)C1=C(C(=C(C(=C1F)C)[N+](=O)[O-])F)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 2,3,6-trifluoro-4-methyl-5-nitrotoluene (1.9 g) are added 2-methoxyethanol (9.9 ml), water (1.1 ml), N-methylpiperazine (4.1 ml) and triethylamine (5.2 ml) and the mixture is refluxed for 25 hours. After the reaction is completed, water is added and the resultant is extracted with diethyl ether, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the residue is purified by silica-gel column-chromatography (dichloromethane : methanol=40 : 1) to give 2-(4-methyl-1-piperazinyl)-3,6-difluoro-4-methyl-5 -nitrotoluene (1.73 g). |
Here is a chemical reaction formula: Reactants are:m2_m3_m1_m4:FC1=C(N)C(=CC(=C1C)F)CSC, Reagents are:m2_m3_m1_m4:[Ni];m2_m3_m1_m4:C(C)O;m2_m3_m1_m4:C(C)O, and Products are 0:FC1=C(N)C(=CC(=C1C)F)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of Raney nickel (50 g) in ethanol (100 ml) is added a solution of 2,4-difluoro-3-methyl-6-methylthiomethylaniline (4.79 g) in ethanol (30 ml) at room temperature with stirring, followed by stirring at room temperature for 30 minutes. The Raney nickel is filtered off and the filtrate is diluted with water, extracted with dichloromethane, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure to give 2,4-difluoro-3,6-dimethylaniline (3.14 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m5:FC1=C(N)C(=CC(=C1C)F)C;m1_m2_m5:F[B-](F)(F)F.[H+];m3_m4:N(=O)[O-].[Na+], Reagents are:m1_m2_m5:O;m3_m4:O, and Products are 0:F[B-](F)(F)F.FC1=C(C(=CC(=C1C)F)C)[N+]#N, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 2,4-difluoro-3,6-dimethylaniline (3.1 g) are added 42% tetrafluoroboric acid (9 ml) and water (4.5 ml) with stirring and under ice-cooling, followed by dropwise addition of a solution of sodium nitrite (1.6 g) in water (3.2 ml) below 10° C. After stirring the mixture at 0° C. for 15 minutes, the resulting crystals are filtered, washed with a mixture of ethanol-diethyl ether (1:2) and then with diethyl ether, followed by drying under reduced pressure to give 2,4-difluoro-3,6-dimethylbenzene diazonium tetrafluoroborate (1.78 g). |
Here is a chemical reaction formula: Reactants are:m1_m2:CC1=C(C(=C(C(=C1C(=O)O)F)F)F)F;m1_m2:[Cl-], Reagents are:, and Products are 0:CC1=C(C(=C(C(=C1C(=O)Cl)F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 6-methyl-2,3,4,5-tetrafluorobenzoic acid (5.60 g) is added thiony chloride (9.8 ml) and the mixture is refluxed for 1 hour. After concentrating, 6-methyl-2,3,4,5-tetrafluorobenzoyl chloride (5.20 g) is obtained as a colorless oil, b.p. 82° C./23 mmHg. |
Here is a chemical reaction formula: Reactants are:m3_m7:CC1=C(C(=C(C(=C1C(=O)Cl)F)F)F)F;m5_m1_m6:[Mg];m4_m10:S(O)(O)(=O)=O;m2_m9_m8:C(CC(=O)OCC)(=O)OCC, Reagents are:m3_m7:C1(=CC=CC=C1)C;m5_m1_m6:C(Cl)(Cl)(Cl)Cl;m5_m1_m6:C(C)O;m4_m10:O;m2_m9_m8:C1(=CC=CC=C1)C;m2_m9_m8:C(C)O, and Products are 0:CC1=C(C(=C(C(=C1C(=O)C(C(=O)OCC)C(=O)OCC)F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Separately, two drops of carbon tetrachloride are added to a solution of metallic magnesium (0.56 g) in absolute ethanol (0.9 ml). When the reaction starts, a mixture of diethyl malonate (3.6 ml), absolute ethanol (1.6 ml) and anhydrous toluene (6 ml) is added dropwise below 60° C. After stirring at 60° C. for 1 hour, the reaction mixture is cooled to 0° C. and thereto a solution of 6-methyl-2,3,4,5-tetrafluorobenzoyl chloride (5.00 g) prepared above in toluene (5 ml) is added dropwise. After stirring for 30 minutes, a mixture of conc. sulfuric acid (0.4 ml) and water (6 ml) is added and the mixture is extracted with diethyl ether, and the extract is dried over magnesium sulfate and concentrated to give diethyl 6-methyl-2,3,4,5-tetrafluorobenzoylmalonate (8 g) as an yellow oil. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:CC1=C(C(=C(C(=C1C(=O)C(C(=O)OCC)C(=O)OCC)F)F)F)F;m1_m3_m2:C1(=CC=C(C=C1)S(=O)(=O)O)C, Reagents are:m1_m3_m2:O, and Products are 0:CC1=C(C(=C(C(=C1C(=O)CC(=O)OCC)F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To diethyl 6-methyl-2,3,4,5-tetrafluorobenzoylmalonate (8 g) are added water (20 ml) and p-toluenesulfonic acid (80 mg) and the mixture is refluxed for 2.5 hours. After cooling, the resultant is extracted with diethyl ether, and the extract is dried over magnesium sulfate and concentrated to give ethyl 6-methyl-2,3,4,5-tetrafluorobenzoylacetate (4.5 g). |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:CC1=C(C(=C(C(=C1C(=O)CC(=O)OCC)F)F)F)F;m1_m2_m3:C(C)(=O)OC(C)=O;m1_m2_m3:C(OCC)([O-])[O-], Reagents are:, and Products are 0:CC1=C(C(=C(C(=C1C(=O)C(C(=O)OCC)=COCC)F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To ethyl 6-methyl-2,3,4,5-tetrafluorobenzoylacetate (4.20 g) are added acetic anhydride (3.7 g) and ethyl orthoformate (4 ml) and the mixture is refluxed for 1 hour. After concentrating, ethyl 2-(6-methyl-2,3,4,5-tetrafluorobenzoyl)-3-ethoxyacrylate (5 g) is obtained. |
Here is a chemical reaction formula: Reactants are:m1_m3:CC1=C(C(=C(C(=C1C(=O)C(C(=O)OCC)=COCC)F)F)F)F;m2:C1(CC1)N, Reagents are:m1_m3:C(C)O, and Products are 0:CC1=C(C(=C(C(=C1C(=O)C(C(=O)OCC)=CNC1CC1)F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Ethyl 2-(6-methyl-2,3,4,5-tetrafluorobenzoyl)-3-ethoxyacrylate (5 g) is dissolved in ethanol (25 ml) and thereto cyclopropylamine (1.0 g) is added dropwise under ice-cooling. After stirring at room temperature for 30 minutes, the mixture is concentrated and the residue is purified with column chromatography (silica-gel, dichloromethane : n-hexane=1 : 1) to give ethyl 2-(6-methyl-2,3,4,5-tetrafluorobenzoyl)-3 -cyclopropylaminoacrylate (4.74 g), as white plates, m.p. 78°-79° C. (recrystallized from petroleum ether--n-hexane). |
Here is a chemical reaction formula: Reactants are:m2:Cl;m1_m3:C1(CC1)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)C)=O)C(=O)OCC, Reagents are:m1_m3:C(C)(=O)O, and Products are 0:C1(CC1)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)C)=O)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To ethyl 1-cyclopropyl-6,7,8-trifluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (4.10 g) are added 90% acetic acid--conc. hydrochloric acid (4 : 1, 81.25 ml) and the mixture is refluxed for 2 hours. After cooling, the precipitated crystals are isolated, washed with water, ethanol, and diethyl ether in this order to give 1-cyclopropyl-6,7,8-trifluoro-5-methyl-1,4,-dihydro-4 -oxoquinoline-3-carboxylic acid (3.47 g), as white needles, m.p. 218°-220° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m6_m3_m5:FC1=C(C(=C(C(=C1F)Cl)[N+](=O)[O-])F)C;m1_m2_m6_m3_m5:C(C)O;m1_m2_m6_m3_m5:CN1CCNCC1, Reagents are:m1_m2_m6_m3_m5:C(C)N(CC)CC;m1_m2_m6_m3_m5:O;m4:O, and Products are 0:CN1CCN(CC1)C1=C(C(=C(C(=C1F)Cl)[N+](=O)[O-])F)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 2,3,6-trifluoro-4-chloro-5-nitrotoluene (0.17 g) are added ethanol (3.3 ml), water (0.5 ml), N-methylpiperazine (0.45 ml) and triethylamine (0.56 ml) and the mixture is refluxed for 24 hours. After the reaction is completed, water is added to the reaction mixture and the mixture is extracted with diethyl ether, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure and the residue is purified by silica-gel column-chromatography (eluent; dichloromethane: methanol=20 : 1) to give 2-(4-methyl-1-piperazinyl)-3,6-difluoro-4-chloro-5-nitrotoluene (0.13 g). |
Here is a chemical reaction formula: Reactants are:m2:S(=O)(Cl)Cl;m1:ClC=1C(=C(C(=O)O)C(=C(C1F)F)C)F, Reagents are:, and Products are 0:ClC=1C(=C(C(=O)Cl)C(=C(C1F)F)C)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing 3-chloro-2,4,5-trifluoro-6-methylbenzoic acid (185 mg) and thionyl chloride (600 μl), the procedure of Reference Example 18 is repeated to give 3-chloro-2,4,5-trifluoro-6-methylbenzoyl chloride (183 mg). |
Here is a chemical reaction formula: Reactants are:m2:C1(=CC=C(C=C1)S(=O)(=O)O)C;m1:ClC=1C(=C(C(=O)C(C(=O)OCC)C(=O)OCC)C(=C(C1F)F)C)F, Reagents are:, and Products are 0:ClC=1C(=C(C(=O)CC(=O)OCC)C(=C(C1F)F)C)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing diethyl 3-chloro-2,4,5-trifluoro-6-methylbenzoylmalonate (320 mg) and p-toluenesulfonic acid (3 mg), the procedure of Reference Example 19 is repeated to give ethyl 3-chloro-2,4,5-trifluoro-6-methylbenzoylacetate (300 mg), as brown oil. |
Here is a chemical reaction formula: Reactants are:m2:C(OCC)([O-])[O-];m1:ClC=1C(=C(C(=O)CC(=O)OCC)C(=C(C1F)F)C)F, Reagents are:, and Products are 0:ClC=1C(=C(C(=O)C(C(=O)OCC)=COCC)C(=C(C1F)F)C)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 3-chloro-2,4,5-trifluoro-6-methylbenzoylacetate (300 mg) and ethyl orthoformate (550 mg), the procedure of Reference Example 20 is repeated to give ethyl 2-(3-chloro-2,4,5-trifluoro-6-methylbenzoyl)-3-ethoxyacrylate (360 mg), as brown oil. |
Here is a chemical reaction formula: Reactants are:m1:ClC=1C(=C(C(=O)C(C(=O)OCC)=COCC)C(=C(C1F)F)C)F;m2:C1(CC1)N, Reagents are:, and Products are 0:ClC=1C(=C(C(=O)C(C(=O)OCC)=CNC2CC2)C(=C(C1F)F)C)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 2-(3-chloro-2,4,5-trifluoro-6-methylbenzoyl)-3-ethoxyacrylate (360 mg) and cyclopropylamine (60 mg), the procedure of Reference Example 21 is repeated to give ethyl 2-(3-chloro-2,4,5-trifluoro-6-methylbenzoyl)-3-cyclopropylaminoacrylate (410 mg), as brown oil. |
Here is a chemical reaction formula: Reactants are:m1:ClC=1C(=C(C(=O)C(C(=O)OCC)=CNC2CC2)C(=C(C1F)F)C)F;m2:[H-].[Na+], Reagents are:, and Products are 0:C1(CC1)N1C=C(C(C2=C(C(=C(C(=C12)Cl)F)F)C)=O)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 2-(3-chloro-2,4,5-trifluoro-6-methylbenzoyl)-3-cyclopropylaminoacrylate (410 mg) and 60% sodium hydride (35 mg), the procedure of Reference Example 22 is repeated to give ethyl 1-cyclopropyl-6,7-difluoro-8-chloro-5-methyl-1,4-dihydro-4 -oxoquinoline-3-carboxylate (70 mg), as pale yellow powder (recrystallized from dichloromethane --n-haxane), m.p. 153°-154° C. |
Here is a chemical reaction formula: Reactants are:m1:C(C)C1=C(C(=O)C(C(=O)OCC)C(=O)OCC)C(=C(C(=C1F)F)F)F;m2:C1(=CC=C(C=C1)S(=O)(=O)O)C, Reagents are:, and Products are 0:C(C)C1=C(C(=O)CC(=O)OCC)C(=C(C(=C1F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing diethyl 2-ethyl-3,4,5,6-tetrafluorobenzoylmalonate (17.2 g) and p-toluenesulfonic acid (0.25 g), the procedure of Reference Example 19 is repeated to give ethyl 2-ethyl-3,4,5,6-tetrafluorobenzoylacetate (11.09 g). |
Here is a chemical reaction formula: Reactants are:m2:C(OCC)([O-])[O-];m1:C(C)C1=C(C(=O)CC(=O)OCC)C(=C(C(=C1F)F)F)F, Reagents are:, and Products are 0:C(C)C1=C(C(=O)C(C(=O)OCC)=COCC)C(=C(C(=C1F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 2-ethyl-3,4,5,6-tetrafluorobenzoylacetate (8 g) and ethyl orthoformate (6.1 g), the procedure of Reference Example 20 is repeated to give ethyl 2-(2-ethyl-3,4,5,6-tetrafluorobenzoyl)-3-ethoxyacrylate. |
Here is a chemical reaction formula: Reactants are:m2:C1(CC1)N;m1:C(C)C1=C(C(=O)C(C(=O)OCC)=COCC)C(=C(C(=C1F)F)F)F, Reagents are:, and Products are 0:C(C)C1=C(C(=O)C(C(=O)OCC)=CNC2CC2)C(=C(C(=C1F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-ethyl-3,4,5,6-tetrafluorobenzoyl)-3-ethoxyacrylate and cyclopropylamine, the procedure of Reference Example 21 is repeated to give ethyl 2-(2-ethyl-3,4,5,6-tetrafluorobenzoyl)-3-cyclopropylaminoacrylate. |
Here is a chemical reaction formula: Reactants are:m1:C(C)C1=C(C(=O)C(C(=O)OCC)=CNC2CC2)C(=C(C(=C1F)F)F)F;m2:[H-].[Na+], Reagents are:, and Products are 0:C1(CC1)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)CC)=O)C(=O)OCC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-ethyl-3,4,5,6-tetrafluorobenzoyl)-3-cyclopropylaminoacrylate (8.71 g) and 60% sodium hydride (1.09 g), the procedure of Reference Example 22 is repeated to give ethyl 1-cyclopropyl-6,7,8-trifluoro-5-ethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (5 g), as white powder, m.p. 139°-140° C. |
Here is a chemical reaction formula: Reactants are:m2:Cl;m1:C1(CC1)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)CC)=O)C(=O)OCC;m3:O, Reagents are:m4:C(C)(=O)O, and Products are 0:C1(CC1)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)CC)=O)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 1-cyclopropyl-6,7,8-trifluoro-5-ethyl-1,4-dihydro-4 -oxoquinoline-3-carboxylate (5 g), conc. hydrochloric acid (11 ml), water (4.4 ml) and acetic acid (44 ml), the procedure of Reference Example 23 is repeated to give 1-cyclopropyl-6,7,8-trifluoro-5-ethyl-1,4-dihydro-4 -oxoquinoline-3-carboxylic acid (4.2 g), as white powder, m.p. 197°-198° C. |
Here is a chemical reaction formula: Reactants are:m1:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=C(C(=C1F)F)F)F;m2:C(C)N, Reagents are:, and Products are 0:CC1=C(C(=O)C(C(=O)OCC)=CNCC)C(=C(C(=C1F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-ethoxyacrylate (10.0 g) and ethylamine gas, the procedure of Reference Example 21 is repeated to give ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-ethylaminoacrylate (9.0 g, white crystals), which is then treated with 60% sodium hydride (1.30 g) as in REFERENCE EXAMPLE 22 to give ethyl 1-ethyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (6.76 g), as pale yellow needles (recrystallized from dichloromethane--n-hexane), m.p. 197°-198° C. |
Here is a chemical reaction formula: Reactants are:m2:Cl;m1:C(C)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)C)=O)C(=O)OCC, Reagents are:m3:C(C)(=O)O, and Products are 0:C(C)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)C)=O)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 1-ethyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-caboxylate (6.51 g) and conc. hydrochloric acid : 90% acetic acid (1:4) (100 ml), the procedure of Reference Example 23 is repeated to give 1-ethyl-5-methyl-6,7,8-trifluoro-1,4-dihydro-4 -oxoquinoline-3-carboxylic acid (5.53 g), as colorless needles (recrystallized from dichloromethane--n-hexane), m.p. 203°-204° C. |
Here is a chemical reaction formula: Reactants are:m1:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=C(C(=C1F)F)F)F;m2:FC1=C(N)C=CC(=C1)F, Reagents are:, and Products are 0:CC1=C(C(=O)C(C(=O)OCC)=CNC2=C(C=C(C=C2)F)F)C(=C(C(=C1F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-ethoxyacrylate (5.0 g) and 2,4-difluoroaniline (2.02 g), the procedure of Reference Example 21 is repeated to give ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-(2,4-difluorophenyl)aminoacrylate, which is then treated with 60% sodium hydride as in Reference Example 22 to give ethyl 1-(2,4-difluorophenyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (4.6 g), as pale yellow prisms (recrystallized from dichloromethane--n-hexane), m.p. 156°-157.5° C. |
Here is a chemical reaction formula: Reactants are:m1:FC1=C(C=CC(=C1)F)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)C)=O)C(=O)OCC;m2:Cl, Reagents are:m3:C(C)(=O)O, and Products are 0:FC1=C(C=CC(=C1)F)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)C)=O)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 1-(2,4-difluorophenyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4 -oxoquinoline-3-carboxylate (4.3 g) and conc. hydrochloric acid: 90% acetic acid (1:4) (80 ml), the procedure of Reference Example 23 is repeated to give 1-(2,4-difluorophenyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (2.93 g), as white powder, m.p. 221°-222° C. |
Here is a chemical reaction formula: Reactants are:m2:NC=1SC=CC1;m1:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=C(C(=C1F)F)F)F, Reagents are:, and Products are 0:CC1=C(C(=O)C(C(=O)OCC)=CNC=2SC=CC2)C(=C(C(=C1F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-ethoxyacrylate (5.0 g) and 2-aminothiophene (2.22 g), the procedure of Reference Example 21 is repeated to give ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-(2-thienyl)aminoacrylate, which is then treated with 60% sodium hydride as in Reference Example 22 to give ethyl 1-(2-thienyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (1.05 g), as white powder (recrystallized from ethyl acetate--n-hexane), m.p. 198°-200° C. |
Here is a chemical reaction formula: Reactants are:m2:Cl;m1:S1C(=CC=C1)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)C)=O)C(=O)OCC, Reagents are:m3:C(C)(=O)O, and Products are 0:S1C(=CC=C1)N1C=C(C(C2=C(C(=C(C(=C12)F)F)F)C)=O)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 1-(2-thienyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4 -oxoquinoline-3-carboxylate (1.05 g), conc. hydrochloric acid (10 ml) and 90% acetic acid (40 ml), the procedure of Reference Example 23 is repeated to give 1-(2-thienyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (0.93 g), as white powder, m.p. 221°-222.5° C. |
Here is a chemical reaction formula: Reactants are:m1:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=C(C(=C1F)F)F)F;m2:C(O)CN, Reagents are:, and Products are 0:CC1=C(C(=O)C(C(=O)OCC)=CNCCO)C(=C(C(=C1F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-ethoxyacrylate (7.0 g) and ethanol amine (1.33 ml), the procedure of Reference Example 21 is repeated to give ethyl 2-(2-methyl-3,4,5,6-tetraflurobenzoyl)-3-(2-hydroxyethyl)aminoacrylate. To the product are added pyridine (70 ml) and acetic anhydride (2.57 ml) and the mixture is stirred at room temperature over-night. After concentration, the resultant is diluted with water, subjected to extraction with dichloromethane, and the extract is washed with water and then with a saturated saline solution and dried to give ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-(2-acetyloxyethyl) aminoacrylate, which is then treated with 60% sodium hydride (1.09 g) as in Reference Example 22 to give ethyl 1-(2-acetyloxyethyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4 -oxoquinoline-3carboxylate (6.15 g), as colorless prisms (recrystallized from ethyl acetate), m.p. 192°-193° C. |
Here is a chemical reaction formula: Reactants are:m2:Cl;m1:C(C)(=O)OCCN1C=C(C(C2=C(C(=C(C(=C12)F)F)F)C)=O)C(=O)OCC, Reagents are:m3:C(C)(=O)O, and Products are 0:OCCN1C=C(C(C2=C(C(=C(C(=C12)F)F)F)C)=O)C(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 1-(2-acetyloxyethyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4 -oxoquinoline-3-carboxylate (5.80 g) and conc. hydrochloric acid: 90% acetic acid (1:4) (100 ml), the procedure of Reference Example 23 is repeated to give 1-(2-hydroxyethyl)-5-methyl-6,7,8-trifluoro-1,4-dihydro-4 -oxoquinoline-3-carboxylic acid (4.04 g), as pale yellow flakes (recrystallized from ethanol), m.p. 244.5°-247° C. |
Here is a chemical reaction formula: Reactants are:m1:CC1=C(C(=O)C(C(=O)OCC)=COCC)C(=C(C(=C1F)F)F)F;m2:Cl.ClCCN, Reagents are:m3:C(C)N(CC)CC, and Products are 0:CC1=C(C(=O)C(C(=O)OCC)=CNCCCl)C(=C(C(=C1F)F)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Employing ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-ethoxyacrylate (5.0 g), 2-chloroethylamine hydrochloride (1.74 g) and triethylamine (1.97 g), the procedure of Reference Example 21 is repeated to give ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)-3-(2-chloroethyl)aminoacrylate (5.52 g), which is then treated with 60% sodium hydride (0.72 g) as in Reference Example 22 to give ethyl 1-(2-chloroethyl)-5-methyl-6,7,8-trifluoro-l,4-dihydro-4-oxoquinoline-3-carboxylate (3.90 g), as colorless needles (recrystallized from ethyl acetate--n-hexane), m.p. 161.5°-163.5° C. (dec.) |
Here is a chemical reaction formula: Reactants are:m1_m2:CN1CCN(CC1)C=1C(=C(NC2CC2)C(=C(C1F)C)[N+](=O)[O-])C;m1_m2:C(C)OC=C(C(=O)OCC)C(=O)OCC, Reagents are:, and Products are 0:C(C)OC(C(C(=O)OCC)=CN(C1=C(C(=C(C(=C1[N+](=O)[O-])C)F)N1CCN(CC1)C)C)C1CC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To 3-(4-methyl-1-piperazinyl)-4-fluoro-2,5-dimethyl-6-nitro-N-cyclopropylaniline (1.65 g) is added diethyl ethoxymethylenemalonate (1.45 ml) and the mixture is heated at 150° C. for 25 hours. After cooling, the reaction product is purified by silica-gel column-chromatography (dichloromethane : methanol=100 : 1) to give diethyl[N-cyclopropyl-N-[3-(4-methyl-l-piperazinyl)-4 -fluoro-2,5-dimethyl-6-nitrophenyl]aminomethylene]malonate (1.58 g). The product is dissolved in acetic anhydride (7.9 ml) and thereto conc. sulfuric acid (3.16 ml) is added dropwise at 50°-60° C., followed by stirring for 30 minutes. The resultant mixture is poured into ice-water, neutralized, extracted with dichloromethane and the extract is dried. The solvent is distilled off under reduced pressure. Purification by silica-gel column-chromatography (dichloromethane : methanol =10 : 1) and recrystallization from ethanol--diethyl ether to give ethyl 7-(4-methyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-5,8-dimethyl-1,4-dihydro-4 -oxoquinoline-3-carboxylate (28 mg), as yellow crystals, m.p. 146°-147° C. |
Here is a chemical reaction formula: Reactants are:m1_m3_m2:C(C)(C)(C)OC(=O)NC1CN(CC1C)C1=C(C(=C2C(C(=CN(C2=C1F)C1CC1)C(=O)O)=O)C)F;m1_m3_m2:Cl, Reagents are:m1_m3_m2:C(C)O, and Products are 0:Cl.NC1CN(CC1C)C1=C(C(=C2C(C(=CN(C2=C1F)C1CC1)C(=O)O)=O)C)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture comprising 7-(3-t-butoxycarbonylamino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6, 8-difluoro-5-methyl1,4-dihydro-4-oxoquinoline-3-carboxylic acid (trans form) (125 mg), ethanol (4 ml) and 10% hydrochloric acid (4 ml) is refluxed for 30 minutes. After concentrating, the obtained residue is recrystallized from ethanol to give 7-(3-amino-4-methyl-1-pyrrolidinyl)-1-cyclopropyl-6, 8-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid monohydrochloride (trans form) (63 mg), as pale yellow powder, m.p. 214°-216° C. |
Here is a chemical reaction formula: Reactants are:m3:Cl;m1_m4_m2:N1(CCNCC1)C1=C(C(=C2C(C(=CN(C2=C1F)C1CC1)C(=O)O)=O)C)F;m1_m4_m2:C(C)(=O)OC(C)=O, Reagents are:m1_m4_m2:[OH-].[Na+], and Products are 0:C(C)(=O)N1CCN(CC1)C1=C(C(=C2C(C(=CN(C2=C1F)C1CC1)C(=O)O)=O)C)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 7-(1-piperazinyl)-1-cyclopropyl-6,8-difluoro-5-methyl-1, 4-dihydro-4-oxoquinoline-3carboxylic acid (42 mg) in 5% sodium hydroxide (2 ml) is added acetic anhydride (0.1 ml) at room temperature. After the mixture is made acidic with dilute hydrochloric acid, the resultant is extracted with dichloromethane and the extract is dried over magnesium sulfate. After concentrating, the obtained residue is recrystallized from ethanol to give 7-(4-acetyl-1-piperazinyl)-1-cyclopropyl-6,8-difluoro-5-methyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid (30 mg), as white powder, m.p. 217°-220° C. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C1=CC=CC=C1)N1CCN(CC1)C1=C(C(=C2C(C(=CN(C2=C1C)C1CC1)C(=O)O)=O)C)F, Reagents are:m1_m2_m3:C(C)O;m1_m2_m3:[Pd], and Products are 0:N1(CCNCC1)C1=C(C(=C2C(C(=CN(C2=C1C)C1CC1)C(=O)O)=O)C)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 7-(4-benzyl-1-piperazinyl)-1-cyclopropyl-6-fluoro-5,8-dimethyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid (150 mg) in ethanol (20 ml) is added 10% Pd-C (50 mg) and the catalytic reduction is carried out at 70° C. under atomospheric pressure. After filtering off the 10% Pd-C, the filtrate is concentrated. The residue is recrystallized from dimethylformamide to give 7-(1-piperazinyl)-1-cyclopropyl-6-fluoro-5,8-dimethyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid (64 mg), m.p. 185°-187° C., as pale yellow needles. |
Here is a chemical reaction formula: Reactants are:m3:C([O-])([O-])=O.[K+].[K+];m1_m2:C(C)OC(=O)NC1CN(CC1)C1=C(C(=C2C(C(=CN(C2=C1C)C1CC1)C(=O)OCC)=O)C)F;m1_m2:[OH-].[K+], Reagents are:m4:C(C)(=O)O, and Products are 0:NC1CN(CC1)C1=C(C(=C2C(C(=CN(C2=C1C)C1CC1)C(=O)O)=O)C)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To ethyl 7-(3-ethoxycarbonylamino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-5, 8-dimethyl-1,4-dihydro-4-oxoquinoline-3-carboxylate (130 mg) is added 5% aqueous potassium hydroxide solution (3.2 ml) and the mixture is refluxed for 4 hours. After cooling, the reaction mixture is made acidic with acetic acid and then made weak alkaline with potassium carbonate. The resultant is extracted with dichloroethane and the extract is dried, followed by distillating the solvent under reduced pressure. To the residue is added diethyl ether and the precipitated crystals are filtered to give 7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-5, 8-dimethyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (30 mg), m.p. 96°-98° C., as pale yellow needles. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2_m3_m4:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)O;m1_m5_m2_m3_m4:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m1_m5_m2_m3_m4:C(C1=CC=CC=C1)(=O)O;m1_m5_m2_m3_m4:N(=NC(=O)OCC)C(=O)OCC, Reagents are:m7_m6:O;m7_m6:C(C)(=O)OCC;m1_m5_m2_m3_m4:O1CCCC1, and Products are 0:C(C1=CC=CC=C1)(=O)O[C@@H](C)[C@@]1(OC1)C1=C(C=C(C=C1)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (16.1 g) in tetrahydrofuran (320 ml) were added triphenylphosphine (63.3 g), benzoic acid (29.5 g) and diethyl azodicarboxylate (42.0 g) under ice-cooling. The mixture was stirred for 6 hours at room temperature under argon atmosphere. To the reaction mixture were added ethyl acetate (800 ml) and water (500 ml). The separated aqueous layer was extracted with ethyl acetate (200 ml). The combined organic layers were washed with water and a saturated saline, dried over magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=15:1→7:1) for purification to give [(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl] benzoate (19.2 g) as a colorless oily substance. |
Here is a chemical reaction formula: Reactants are:m1:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@H](C)O;m2:N1N=CC=C1, Reagents are:, and Products are 0:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1N=CC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (569 mg) and pyrazole, (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(1H-pyrazol-1-yl)ethyl]oxirane (166 mg) was obtained by the same way as in Reference Example 2. |
Here is a chemical reaction formula: Reactants are:m2:N1N=NC=C1;m3:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1N=CC=N1;m1:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@H](C)O, Reagents are:, and Products are 0:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1N=NC=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (497 mg) and 1H-1,2,3-triazole, (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(2H-1,2,3-triazol-2-yl)ethyl]oxirane (150 mg) and (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(1H-1,2,3-triazol-1-yl)ethyl]oxirane (204 mg) were obtained by the same way as in Reference Example 2. |
Here is a chemical reaction formula: Reactants are:m2:N1=CN=C2N=CNC2=C1;m1:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@H](C)O, Reagents are:, and Products are 0:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1C2=NC=NC=C2N=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (1.03 g) and purine (500 mg), (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(9H-9-purinyl)ethyl]oxirane (600 mg) was obtained by the same way as in Reference Example 2. |
Here is a chemical reaction formula: Reactants are:m1:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@H](C)O;m2:N1C=NC2=NC=CC=C21;m3:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1C=NC=2C1=NC=CC2, Reagents are:, and Products are 0:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1C=NC2=NC=CC=C21, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (981 mg) and 1H-imidazo[4,5-b]pyridine (472 mg), (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(3H-3-imidazo[4,5-b]pyridyl)ethyl]oxirane (501 mg) and (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(1H-1-imidazo[4,5-b]pyridyl)ethyl]oxirane (271 mg) were obtained by the same way as in Reference Example 2. |
Here is a chemical reaction formula: Reactants are:m2:N1N=CN=C1;m1:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@H](C)O, Reagents are:, and Products are 0:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1N=CN=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (1.17 g) and 1H-1,2,4-triazole (404 mg), (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(1H-1,2,4-triazol-1-yl)ethyl]oxirane (830 mg) was obtained by the same way as in Reference Example 2. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2_m3_m4:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@H](C)O;m1_m5_m2_m3_m4:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1;m1_m5_m2_m3_m4:N1N=NN=C1;m1_m5_m2_m3_m4:N(=NC(=O)OCC)C(=O)OCC, Reagents are:m1_m5_m2_m3_m4:O1CCCC1;m7_m6:O;m7_m6:C(C)(=O)OCC, and Products are 0:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1N=CN=N1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (200 mg) in tetrahydrofuran (5 ml) were added triphenylphosphine (787 mg), tetrazole (210 mg) and diethyl azodicarboxylate (0.47 ml) at 0° C. under argon atmosphere. The mixture was stirred for 16 hours at room temperature. To the reaction mixture were added ethyl acetate (30 ml) and water (15 ml). The separated aqueous layer was extracted with ethyl acetate (20 ml). The combined organic layers were washed with water and saturated saline, dried (MgSO4) and concentrated. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4:1→3:1→2:1) to give (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(2H-tetrazol-2-yl)ethyl]oxirane (176 mg). |
Here is a chemical reaction formula: Reactants are:m1:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@H](C)O;m2:N1N=NC=C1, Reagents are:, and Products are 0:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1N=CC=N1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (202 mg) and 1H-1,2,3-triazole (0.17 ml), (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(2H-1,2,3-triazol-2-yl)ethyl]oxirane (172 mg) was obtained by the same way as in Reference Example 10. |
Here is a chemical reaction formula: Reactants are:m3:Cl;m2:[OH-].[Na+];m1_m4:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)OC(C1=CC(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-])=O, Reagents are:m1_m4:CO, and Products are 0:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: [(1R)-1-[(2R)-2-(2,4-Difluorophenyl)-2-oxiranyl]ethyl]3,5-dinitrobenzoate (50 g) was dissolved in methanol (2 liters). To the solution was added dropwise 1N sodium hydroxide aqueous solution (255 ml) at room temperature. The mixture was stirred for an hour at room temperature and neutralized with 1N hydrochloric acid (127 ml). Methanol was distilled off under reduced pressure. To the residue were added ethyl acetate (1 liter) and water (200 ml). The mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline (200 ml), dried over magnesium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1:3) to give (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (25 g) as a pale yellow oily substance. |
Here is a chemical reaction formula: Reactants are:m5_m9:[Cl-].[NH4+];m1_m6_m2:BrC1=CC=C(C=C1)Cl;m1_m6_m2:[Mg];m3_m7:BrC1=CC=C(C=C1)Cl;m4_m8:O1C(CCCC1)O[C@@H](C(=O)N1CCOCC1)C, Reagents are:m5_m9:O;m1_m6_m2:O1CCCC1;m3_m7:O1CCCC1;m4_m8:O1CCCC1, and Products are 0:ClC1=CC=C(C=C1)C([C@@H](C)OC1OCCCC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 1-bromo-4-chlorobenzene (20 g) in tetrahydrofuran (260 ml) was added magnesium (turnings, 7.47 g). The mixture was vigorously stirred at room temperature. When the temperature of the mixture reached 40° C., the reaction vessel was cooled in a water bath. A solution of 1-bromo-4-chlorobenzene (38.9 g) in tetrahydrofuran (90 ml), was added dropwise to the mixture at 34°-40° C., followed by stirring for an hour at 30° C. To the mixture was added dropwise a solution of 4-[(2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionyl]morpholine (60 g) in tetrahydrofuran (60 ml) over the period of 15 minutes at 0° C. The mixture was stirred for 3 hours at room temperature. To the reaction mixture were added a saturated aqueous ammonium chloride solution (120 ml) and water (100 ml). The mixture was extracted with ethyl acetate (500 ml). The organic layer was washed with water, dried over magnesium sulfate and distilled under reduced pressure. The residue was purified by silica gel column chromatography (silica gel 900 g, eluent: hexane/ethyl acetate=30:1→10:1) to give (2R)-4'-chloro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (66 g) as a pale yellow oily substance. |
Here is a chemical reaction formula: Reactants are:m2:[Mg];m3_m4:[Cl-].[NH4+];m3_m4:O;m6_m5_m7_m1:O1C(CCCC1)O[C@@H](C(=O)N1CCOCC1)C;m6_m5_m7_m1:BrC1=C(C=CC=C1)F, Reagents are:m6_m5_m7_m1:O1CCCC1;m6_m5_m7_m1:C(C)Br, and Products are 0:FC1=C(C=CC=C1)C([C@@H](C)OC1OCCCC1)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In tetrahydrofuran (100 ml) were dissolved 1-bromo-2-fluorobenzene (5.6 ml), ethyl bromide (0.37 ml) and 4-[(2R)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionyl]morpholine (11.3 g). To the mixture was added magnesium (turnings, 1.33 g). The mixture was stirred for 2 hours at room temperature. To the reaction mixture were added a saturated aqueous ammonium chloride solution (40 ml) and water (40 ml). The mixture was extracted with ethyl acetate (200 ml). The organic layer was washed with water, dried over magnesium sulfate and distilled under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=10:1→8:1) to give (2R)-2'-fluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (8.7 g) as a pale yellow oily substance. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:ClC1=CC=C(C=C1)[C@@](CN1N=CN=C1)([C@@H](C)O)O;m1_m2_m4_m3:C(C)N(CC)CC;m1_m2_m4_m3:CS(=O)(=O)Cl, Reagents are:m1_m2_m4_m3:C(C)(=O)OCC, and Products are 0:CS(=O)(=O)O[C@@H]([C@@](CN1N=CN=C1)(O)C1=CC=C(C=C1)Cl)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of (2R,3R)-2-(4-chlorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (12.4 g) and triethylamine (7.6 ml) in ethyl acetate (200 ml) was added dropwise methanesulfonyl chloride (6.25 g) under ice-cooling. After stirring for 45 minutes at room temperature, the reaction mixture was washed with water and saturated saline, dried over magnesium sulfate and distilled under reduced pressure to give (2R,3R)-2-(4-chlorophenyl)-2-hydroxy-1-(1H-1,2,4-triazol-1-yl)-3-butyl methanesulfonate. |
Here is a chemical reaction formula: Reactants are:m3:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1C=NC2=NC=NC(=C12)OC;m1:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@H](C)O;m2:COC1=C2NC=NC2=NC=N1, Reagents are:, and Products are 0:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1C2=NC=NC(=C2N=C1)OC, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (523 mg) and 6-methoxypurine 1/2 hydrate (415 mg), (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-[6-methoxy-7(7H)purinyl]ethyl]oxirane (205 mg) and (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-[6-methoxy-9(9H)-purinyl]ethyl]oxirane (183 mg) were obtained as a white powder respectively by the same way as in Reference Example 2. |
Here is a chemical reaction formula: Reactants are:m2:CC1=C2NC=NC2=NC=N1;m1:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@H](C)O, Reagents are:, and Products are 0:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1C2=NC=NC(=C2N=C1)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (587 mg) and 6-methylpurine (353 mg), (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-[6-methyl-9(9H)-purinyl]ethyl]oxirane (383 mg) was obtained as a white powder by the same way as in Reference Example 2. |
Here is a chemical reaction formula: Reactants are:m2:ClC1=C2NC=NC2=NC=N1;m1:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@H](C)O, Reagents are:, and Products are 0:ClC1=C2N=CN(C2=NC=N1)[C@H](C)[C@@]1(OC1)C1=C(C=C(C=C1)F)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (607 mg) and 6-chloropurine (422 mg), (2S)-2-[(1R)-1-[6-chloro-9(9H)-purinyl]ethyl]-2-(2,4-difluorophenyl)oxirane (440 mg) was obtained as a white powder by the same way as in Reference Example 2. |
Here is a chemical reaction formula: Reactants are:m2:ClC1=NC(=C2NC=NC2=N1)Cl;m1:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@H](C)O, Reagents are:, and Products are 0:ClC1=NC(=C2N=CN(C2=N1)[C@H](C)[C@@]1(OC1)C1=C(C=C(C=C1)F)F)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using (1S)-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (578 mg) and 2,6-dichloropurine (490 mg), (2S)-2-[(1R)-1-[2,6-dichloro-9(9H)-purinyl]ethyl]-2-(2,4-difluorophenyl)oxirane (168 mg) was obtained by the same way as in Reference Example 2. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4:N1N=CN=C1;m1_m2_m3_m4:FC1=C(C=CC=C1)[C@@]1(O[C@H]1C)CN1N=CN=C1;m1_m2_m3_m4:C([O-])([O-])=O.[Li+].[Li+];m1_m2_m3_m4:CN(C=O)C, Reagents are:m5:C(C)(=O)OCC, and Products are 0:N1(N=CN=C1)C[C@]([C@@H](C)N1N=CN=C1)(O)C1=C(C=CC=C1)F, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1H-1,2,4-triazole (1.17 g), (2R,3S)-2-(2-fluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane (2 g), lithium carbonate (6.32 g) and dimethylformamide (40 ml) was stirred for 24 hours at 110° C. After cooling, to the mixture was added ethyl acetate (50 ml). The mixture was filtered to remove insoluble substances. The filtrate was distilled under reduced pressure. The residue was dissolved in ethyl acetate (100 ml). The mixture was washed with saturated saline (30 ml×2). The ethyl acetate layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure. The residue was purified by silica gel chromatography (silica gel 50 g, eluent: ethyl acetate/acetone=4:1) to give (2R,3R)-1,3-bis(1H-1,2,4-triazol-1-yl)-2-(2-fluorophenyl)-2-butanol (1.32 g). |
Here is a chemical reaction formula: Reactants are:m4_m8:O;m5_m1_m6:[H-].[Na+];m2:N1C=NC=C1;m3_m7:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1N=CC=C1, Reagents are:m4_m8:C(C)(=O)OCC;m5_m1_m6:CN(C=O)C;m3_m7:CN(C=O)C, and Products are 0:FC1=C(C=CC(=C1)F)[C@@](CN1C=NC=C1)([C@@H](C)N1N=CC=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: In dimethylformamide (2 ml) was dispersed 60% sodium hydride in oil (52 mg). Imidazole (89 mg) was added to the dispersion under ice-cooling and the mixture was stirred for 15 minutes at room temperature. To the mixture was added a solution of (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(1H-pyrazol-1-yl)ethyl]oxirane (166 mg) in dimethylformamide (1 ml). The mixture was heated for 5 hours at 50° C. and cooled. To the reaction mixture were added cold water (5 ml) and ethyl acetate (30 ml). The separated aqueous layer was extracted twice with ethyl acetate. The combined ethyl acetate layers were washed with water and saturated saline, dried over magnesium sulfate and distilled under reduced pressure. The residue was allowed to stand to crystallize. The obtained crystals were recrystallized from ethyl acetate-hexane to form the title compound (Compound 1, 193 mg) as colorless prisms. |
Here is a chemical reaction formula: Reactants are:m3_m7:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1N=CN=N1;m1_m2_m5_m6:N1N=CN=C1;m1_m2_m5_m6:[H-].[Na+];m4_m8:O, Reagents are:m3_m7:CN(C=O)C;m1_m2_m5_m6:CN(C=O)C;m4_m8:C(C)(=O)OCC, and Products are 0:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)N1N=CN=N1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1H-1,2,4-Triazole (48 mg) was added to a dispersion of 60% sodium hydride in oil (27 mg) in dimethylformamide (1.1 ml) under ice-cooling and the resulting mixture was stirred for 10 minutes at room temperature. After addition of a solution of (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(2H-tetrazol-2-yl)ethyl]oxirane (89 mg) in dimethylformamide (0.7 ml), the mixture was heated for 5 hours at 50° C. and cooled. Cold water (10 ml) and ethyl acetate (20 ml) were added to the reaction mixture. The separated aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate and distilled under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1:1→2:1→ethyl acetate) to give the title compound (Compound 4, 60 mg, 53%) as a colorless oily substance. |
Here is a chemical reaction formula: Reactants are:m2_m5_m6:[H-].[Na+];m1:N1N=CN=C1;m4_m8:O;m3_m7:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1N=NC=C1, Reagents are:m2_m5_m6:CN(C=O)C;m4_m8:C(C)(=O)OCC;m3_m7:CN(C=O)C, and Products are 0:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)N1N=NC=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 1H-1,2,4-Triazole (63 mg) was added under ice-cooling to a dispersion of 60% sodium hydride in oil (36 mg) in dimethylformamide (1.5 ml) and the resulting mixture was stirred for 10 minutes at room temperature. To the mixture was added a solution of (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-(1H-1,2,3-triazol-1-yl)ethyl]oxirane (116 mg) in dimethylformamide (0.8 ml), followed by heating for 5 hours at 50° C. and cooling. Cold water (10 ml) and ethyl acetate (20 ml) were added to the reaction mixture. The separated aqueous layer was extracted twice with ethyl acetate. The combined ethyl acetate layers were washed with water and saturated saline, dried over anhydrous magnesium sulfate and distilled under reduced pressure. The residue was purified by silica gel column chromatography (acetone/dichlormethane=1:2→1:1). The obtained crystals were recrystallized from diisopropyl ether to give the title compound (Compound 6, 66 mg, 45%) as colorless crystals. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:O.O.O.[F-].C(CCC)[N+](CCCC)(CCCC)CCCC;m1_m2_m3:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)N1C=NN=C1)O[Si](C)(C)C, Reagents are:m1_m2_m3:O1CCCC1, and Products are 0:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)N1C=NN=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Tetrabutylammonium fluoride trihydrate (663 mg) was added to a solution of (2R,3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-(4H-1,2,4-triazol-4-yl)-2-trimethylsilyloxybutane (750 mg) in tetrahydrofuran (50 ml). The mixture was stirred for 30 minutes at room temperature, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/hexane=2:1→ethyl acetate→ethyl acetate/methanol=10:1) to give Compound 20 (620 mg) as a white powder. |
Here is a chemical reaction formula: Reactants are:m2:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1C2=NC=NC(=C2N=C1)OC;m1:N1N=CN=C1, Reagents are:, and Products are 0:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)N1C2=NC=NC(=C2N=C1)OC)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 1H-1,2,4-triazole (74 mg) and (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-[6-methoxy-9(9H)-purinyl]ethyl]oxirane (183 mg), Compound 47 (171 mg) was obtained as colorless prisms by the same way as in Example 1. |
Here is a chemical reaction formula: Reactants are:m2:FC1=C(C=CC(=C1)F)[C@]1(OC1)[C@@H](C)N1C2=NC=NC(=C2N=C1)C;m1:N1N=CN=C1, Reagents are:, and Products are 0:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)N1C2=NC=NC(=C2N=C1)C)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 1H-1,2,4-triazole (167 mg) and (2S)-2-(2,4-difluorophenyl)-2-[(1R)-1-[6-methyl-9(9H)-purinyl]ethyl]oxirane (388 mg), Compound 48 (79 mg) was obtained as colorless prisms by the same way as in Exmaple 1. |
Here is a chemical reaction formula: Reactants are:m1:N1N=CN=C1;m2:ClC1=NC(=C2N=CN(C2=N1)[C@H](C)[C@@]1(OC1)C1=C(C=C(C=C1)F)F)Cl, Reagents are:, and Products are 0:N1(N=CN=C1)C1=NC(=C2N=CN(C2=N1)[C@@H]([C@@](CN1N=CN=C1)(O)C1=C(C=C(C=C1)F)F)C)N1N=CN=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using 1H-1,2,4-triazole (59 mg) and (2S)-2-[(1R)-1-[2,6-dichloro-9 (9H)-purinyl]ethyl]-2-(2,4-difluorophenyl) oxirane (168 mg), Compound 50 (21 mg) was obtained as a white powder by the same way as in Example 1. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:C(C)N(CC)CC;m1_m2_m3_m4_m5:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)N1N=NC(=C1)CO)O;m1_m2_m3_m4_m5:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)N1N=NC(=C1)CO)O;m1_m2_m3_m4_m5:CS(=O)(=O)Cl, Reagents are:m6:ClCCl;m1_m2_m3_m4_m5:ClCCl, and Products are 0:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)N1N=NC(=C1)COS(=O)(=O)C)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Triethylamine (0.26 ml) was added dropwise to a solution of (2R,3R)-2-(2,4-difluorophenyl)-3-(4-hydroxy methyl-1H-1,2,3-triazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (Compound 56, 0.6 g) and methanesulfonyl chloride (0.14 ml) in dichloromethane (20 ml) under ice-cooling. The mixture was stirred for 30 minutes at room temperature. After addition of dichloromethane (20 ml), the mixture was washed with water (20 ml) and 5% sodium hydrogen carbonate aqueons solution (20 ml). The organic layer was dried over anhydrous magnesium sulfate and distilled under reduced pressure to give (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methanesulfonyloxymethyl-1H-1,2,3-triazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol as colorless oil. |
Here is a chemical reaction formula: Reactants are:m4:[Cl-].[NH4+];m1_m2_m5:CS(=O)C;m1_m2_m5:C(C(=O)Cl)(=O)Cl;m3_m6:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)N1N=NC(=C1)CO)O, Reagents are:m7:C(C)N(CC)CC;m1_m2_m5:ClCCl;m3_m6:ClCCl, and Products are 0:FC1=C(C=CC(=C1)F)[C@@](CN1N=CN=C1)([C@@H](C)N1N=NC(=C1)C=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Dimethylsulfoxide (1.08 ml) was added dropwise at -78° C. to a solution of oxalyl chloride (1 ml) in dichloromethane (30 ml), followed by stirring for 10 minutes. To the mixture was added dropwise over the period of 5 minutes a solution of (2R,3R)-2-(2,4-difluorophenyl)-3-(4-hydroxymethyl-1H-1,2,3-triazol-1-yl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (2 g) in dichloro-methane (30 ml), followed by stirring for 15 minutes at -78° C. and then for 1 hour at -45° C. To the mixture was added triethylamine (5 ml), followed by stirring for 20 minutes at 0° C. To the mixture was added a saturated aqueous ammonium chloride solution (20 ml). The mixture was extracted with dichloromethane (40 ml). The extract was dried over anhydrous magnesium sulfate and distilled under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 200 g, eluent: ethyl acetate/dichloromethane=3:1) to give Compound 71 (1.49 g), which was crystallized from diisopropyl ether to yield a colorless crystalline powder. |
Here is a chemical reaction formula: Reactants are:m3:BrCC#C;m1_m2_m4:OC1=CC=C(C=O)C=C1;m1_m2_m4:C(=O)([O-])[O-].[K+].[K+], Reagents are:m1_m2_m4:CC(=O)C, and Products are 0:C(C#C)OC1=CC=C(C=O)C=C1, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a stirred suspension of 4-hydroxybenzaldehyde (425.8 g) and K2CO3 (807.6 g) in acetone (2,960 ml) at reflux temper-ature of about 60° C. under a nitrogen atmosphere, was added dropwise 3-bromo-propyne (502.4 g) over a period of 2 hours. The reaction was heated at reflux for 3 more hours. After cooling to room temperature the reaction mixture was filtered and the excess of K2CO3 removed and washed several times with acetone. The filtrate was washed with saturated aqueous solution of NaHCO2 and NaCl. The aqueous phase was extracted with diethyl ether. The combined organic extracts were dried over Na2SO4, filtered and concentrated to a volume of 1 liter. The solution was kept in the refrigerator overnight. The crystals were filtered out and washed with cold diethyl ether. The filtrate was kept in the refrigerator and some more crystals were formed and removed. This procedure was repeated 3 times resulting in 1,385.26 g of 4-(2-propynyloxy) benzaldehyde in 83% yield. The material was analysed by gas chromatography, and shown to be 99.9% pure. Infrared and mass spectroscopic analysis confirmed the structure. |
Here is a chemical reaction formula: Reactants are:m1_m2:C=1C=CC(=C(C1)C(=O)C[C@@H](C(=O)O)N)N;m1_m2:C(C1=CC=CC=C1)=O, Reagents are:, and Products are 0:NC(C(=O)O)CC(C1=CC=CC=C1)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: The aldol reaction of L-kynurenine and benzaldehyde catalyzed by kynureninase was found to proceed to give predominantly (80%) the (αS, γR) diastereomer of α-amino-γ-hydroxybenzenebutanoic acid. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C(C)(C)(C)C=1C(C(=CC(C1)=O)C(C)(C)C)=O;m1_m2_m4_m3:NC1=CC=C(C(=O)O)C=C1;m1_m2_m4_m3:B(F)(F)F, Reagents are:m1_m2_m4_m3:O1CCCC1, and Products are 0:C(C)(C)(C)C=1C(C(=CC(C1)=NC1=CC=C(C=C1)C(=O)O)C(C)(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 22 g (0.10 mole) of 2,6-di(tertiary-butyl)-p-benzoquinone, 13.7 g (0.10 mole) of 4-aminobenzoic acid, 175 ml of tetrahydrofuran and 1 ml of boron trifluoride: diethyl ether complex was heated on a steam bath for 1.25 hours. The mixture was allowed to cool to about 20° C over 16 hours under a nitrogen atmosphere. Evaporation provided a solid which was washed with hexane and recrystallized from ethanol to provide orange solid 2,6-di(tertiary-butyl)-4-(4'-carboxyphenylimino)-2,5-cyclohexadien-1-one, m.p. 305°-309° C. Analysis: Calculated for C21H25NO3 : % C, 74.3; % H, 7.4; % N, 4.1; Found: % C, 74.2; % H, 7.4; % N, 4.1. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)(C)(C)C=1C(C(=CC(C1)=NC1=CC=C(C=C1)C(=O)O)C(C)(C)C)=O, Reagents are:m1_m2_m3:C(C)O;m1_m2_m3:[Pd], and Products are 0:C(C)(C)(C)C=1C=C(NC2=CC=C(C(=O)O)C=C2)C=C(C1O)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a solution of 5.0 g (0.0147 mole) of 2,6-di(tertiary-butyl)-4-(4'-carboxyphenylimino)-2,5-cyclohexadien-1-one in 300 ml of ethanol was added 0.25 g of 5 percent palladium on charcoal. It was subjected to hydrogenation in a Paar apparatus and filtered. This solvent was removed by evaporation under vacuum and the residue was recrystallized from a 5:2 (v/v) ethanol-water mixture to provide light-orange crystals of 4-(3,5-di-tertiary-butyl-4-hydroxyanilino)benzoic acid, m.p. 241°-243° C. Analysis: Calculated for C21H27NO3 : % C, 73.9; % H, 8.0; % N, 4.1; Found: % C, 73.9; % H, 7.9; % N, 3.8. |
Here is a chemical reaction formula: Reactants are:m1:C(C)(C)(C)C=1C(C(=CC(C1)=O)C(C)(C)C)=O;m2:NC=1C=C(C(=O)O)C=CC1, Reagents are:, and Products are 0:C(C)(C)(C)C=1C(C(=CC(C1)=NC1=CC(=CC=C1)C(=O)O)C(C)(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using the method of Example 1, 2,6-di(tertiary-butyl)-p-benzoquinone was reacted with 3-aminobenzoic acid to provide red-orange crystals of 2,6-di(tertiary-butyl)-4-(3'-carboxyphenylimino)-2,5-cyclohexadien-1-one, m.p. 230°-231° C. Analysis: Calculated for C21H25NO3 : % C, 74.3; % H, 7.4; % N, 4.1; Found: % C, 74.1; % H, 7.6; % N, 3.7. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)O;m1_m2_m3:C(C)(C)(C)C=1C(C(=CC(C1)=NC1=CC=C(C=C1)C(=O)O)C(C)(C)C)=O;m1_m2_m3:C([O-])([O-])=O.[K+].[K+], Reagents are:m4:[Pd];m5:O, and Products are 0:C(C)(C)(C)C=1C=C(NC2=CC=C(C(=O)O)C=C2)C=C(C1O)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: To a mixture of 200 ml of ethanol and 25.0 g (0.0736 mole) of 2,6-di(tertiary-butyl)-4-(4'-carboxyphenylimino)-2,5-cyclohexadien-1-one and 12 g (0.087 mole) of potassium carbonate warmed on a steam bath was added 1.0 g of palladium on charcoal. The mixture was reduced using a Paar apparatus for 2 hours. The mixture was diluted with 300 ml of water, filtered through celite, and the filtrate acidified with 6N hydrochloric acid. The yellow solid precipitate was collected by filtration to provide 4-[3,5-di(tertiary-butyl)-4-hydroxyanilino]benzoic acid, m.p. 241°-242° C. |
Here is a chemical reaction formula: Reactants are:m1_m5_m2:C(C)(C)(C)C=1C=C(NC2=CC=C(C=C2)CC(=O)O)C=C(C1O)C(C)(C)C;m1_m5_m2:C([O-])([O-])=O.[K+].[K+];m3:CI;m4:CI, Reagents are:m1_m5_m2:CN(C=O)C, and Products are 0:C(C)(C)(C)C=1C=C(N(C)C2=CC=C(C=C2)CC(=O)O)C=C(C1O)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of a solution of 6.3 g (0.018 mole) of 4-[3,5-di-(tertiary-butyl)-4-hydroxyanilino]phenylacetic acid in 10 ml of N,N-dimethylformamide and 5 g (0.036 mole) of potassium carbonate was heated on a steam bath until gas evolution ceased. The mixture was allowed to cool to ambient temperature, and 5 milliliters of methyl iodide were then added. The mixture was heated at its boiling temperature and 5 ml aliquots of methyl iodide were added at 20, 45 and 60 minutes. After the mixture had evaporated, the residue was taken up in water and 2N sodium hydroxide solution was added. The mixture was warmed, and the insoluble residue of methyl 4-[3,5-di(tertiary-butyl)-4-hydroxy-N-methyl-anilino] phenylacetate was separated by filtration. The residue was suspended and partially dissolved in 50 ml of methanol, and 10 ml of 2.5N sodium hydroxide solution was added. The mixture was stirred for about 16 hours, diluted with 300 ml of water and 300 ml of diethyl ether, and was then further diluted with about 100 ml of hexane. The mixture was acidified with dilute hydrochloric acid and the aqueous phase was discarded. The organic phase was washed first with 10% sodium bicarbonate solution and then with 5% sodium carbonate solution. The product remained in the organic phase as the sodium salt. The organic phase was acidified with 10% aqueous hydrochloric acid and washed with sodium chloride solution, followed by drying. Evaporation provided a residue which was extracted with 20 ml of boiling benzene. Hexane (6 ml) was added, and the light yellow solid was recrystallized first from 80% aqueous ethanol, and then from benzene to provide fine yellow needles of 4-[3,5-di(tertiary-butyl)-4-hydroxy-N-methylanilino]phenylacetic acid, m.p. 81°-182.5° C. Analysis: Calculated for C23H31NO3 ; % C, 74.8; % H, 8.5; % N, 3.8; Found: % C, 74.8; % H, 8.6; % N, 3.6. |
Here is a chemical reaction formula: Reactants are:m1_m3_m4:C(C)(C)(C)C=1C=C(NC2=CC=C(C(=O)O)C=C2)C=C(C1O)C(C)(C)C;m1_m3_m4:CN(C=O)C;m2:O, Reagents are:m1_m3_m4:CI, and Products are 0:C(C)(C)(C)C=1C=C(N(C)C2=CC=C(C(=O)O)C=C2)C=C(C1O)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A solution of 3.4 g (0.010 mole) of 4-(3,5-di-tertiary-butyl-4-hydroxyanilino)benzoic acid (prepared in Example 1) in 35 ml of N,N-dimethylformamide and 3.5 ml of methyl iodide was heated at 95° C. for about 48 hours under nitrogen. The reaction mixture was poured into cold water and the resulting solid was collected and then taken up in chloroform. The chloroform solution was filtered, washed with water, dried with magnesium sulfate and evaporated to give a tan solid. This material was recrystallized first from benzene and then from a mixture of ethanol and water to give 1.5 g of white crystalline 4-(3,5-di-tertiary-butyl-4-hydroxy-N-methylanilino)benzoic acid, m.p. 240°-244° C. Analysis: Calculated for C22H29NO3 : % C, 74.3; % H, 8.2; % N, 3.9. Found: % C, 74.4; % H, 8.3; % N, 3.5. |
Here is a chemical reaction formula: Reactants are:m4:[Cl-].[Li+];m2:[N-]=[N+]=[N-].[Na+];m3:[Cl-].[NH4+];m1:C(C)(C)(C)C=1C=C(NC=2C=C(C#N)C=CC2)C=C(C1O)C(C)(C)C;m5:Cl, Reagents are:m6:CN(C=O)C, and Products are 0:C(C)(C)(C)C=1C=C(NC=2C=C(C=CC2)C2=NN=NN2)C=C(C1O)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Eight g (0.025 mole) of 3-(3,5-di-t-butyl-4-hydroxyanilino)benzonitrile (from Example 27), 4.9 g (0.075 mole) of sodium azide, 4.0 g (0.075 mole) of ammonium chloride, 1.06 g (0.025 mole) of lithium chloride and 60 ml of N,N-dimethylformamide were combined under a nitrogen atmosphere and heated at 110° C. for 48 hours. The reaction mixture was poured into cold 6N hydrochloric acid and a gummy solid precipitated out. The supernatant was decanted off and the residue dissolved in ethanol. The ethanol solution was diluted with water and a pink solid was collected. This material was recrystallized from a mixture of ethanol and water to give 5.97 g of 5-[3-(3,5-di-t-butyl-4-hydroxyanilino)phenyl]tetrazole, m.p. 231°-233° C. Analysis: Calculated for C21H27N5O: % C, 69.0; % H, 7.4; % N, 19.2; Found: % C, 68.4; % H, 7.6; % N, 18.8. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4:C(C)(C)(C)C=1C=C(NC=2C=C(C(=O)O)C=CC2)C=C(C1O)C(C)(C)C;m1_m2_m4:Cl.CN(CCCl)C;m3:C(C)N(CC)CC, Reagents are:m5:C(C)OCC;m1_m2_m4:CN(C=O)C, and Products are 0:C(C)(C)(C)C=1C=C(NC=2C=C(C(=O)OCCN(C)C)C=CC2)C=C(C1O)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Under a nitrogen atmosphere, 6.0 g (0.0176 mole) of 3-(3,5-di-tertiary-butyl-4-hydroxyanilino)benzoic acid (from Example 13) and 2.53 g (0.0176 mole) of 2-dimethylaminoethyl chloride hydrochloride were dissolved in 17 ml of N,N-dimethylformamide. To this mixture was added 4.9 ml (0.035 mole) of triethylamine and the reaction was heated at 100° C for 25 hours. The reaction temperature was then raised to 120° C. and heating was continued for an additional 28 hours. The reaction mixture was diluted with 10 ml of diethyl ether, then filtered to remove triethylamine hydrochloride. The filtrate was diluted with additional diethyl ether and then shaken with cold 10% hydrochloric acid. A middle layer contained most of the product hydrochloride. It was diluted with water and ether, and basified with solid sodium carbonate. The ether extract was washed with saturated aqueous sodium chloride and then concentrated to give 1.7 g of a tan solid, m.p. 119°-120° C. This material was recrystallized first from 20 ml of cyclohexane and then from a mixture of 10 ml of ethanol and 3 ml of water to give 1.48 g of light yellow prisms of N,N-dimethyl-2-aminoethyl 3-(3,5-di-t-butyl-4-hydroxyanilino)benzoate m.p. 123°-124° C. Analysis: Calculated for C25H36N2O3 : % C, 72.8; % H, 8.8; % N, 6.8. Found: % C, 73.0; % H, 8.8; % N, 6.7. |
Here is a chemical reaction formula: Reactants are:m1:NC1=CC=C(CC#N)C=C1;m2:C(C)(C)(C)C=1C(C(=CC(C1)=O)C(C)(C)C)=O, Reagents are:, and Products are 0:C(C)(C)(C)C=1C(C(=CC(C1)=NC1=CC=C(C=C1)CC#N)C(C)(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: Using the method of Example 1, 4-aminobenzylcyanide was reacted with 2,6-di-tertiary-butyl-p-benzoquinone to give 2,6-di-tertiary-butyl-4-(4'-cyanomethylphenylimino)-2,5-cyclohexadiene-1-one, m.p. 26.5°-127.5° C. Following the reduction method of Example 1, Step B, the corresponding anilino phenylacetonitrile, m.p. 146°-147° C., was obtained. This was converted to 5-[4-(3,5-di-t-butyl-4-hydroxyanilino)benzyl]tetrazole, m.p. 212°-214° C. (dec), following the method of Example 30, but carried out at 110° C. for 48 hours. |
Here is a chemical reaction formula: Reactants are:m2_m3:N1CCOCC1;m1_m4:C(C)(C)(C)C=1C=C(NC=2C=C(C(=O)O)C=CC2)C=C(C1O)C(C)(C)C, Reagents are:m2_m3:C(C)(C)O;m1_m4:C(C)(C)O, and Products are 0:[NH2+]1CCOCC1.C(C)(C)(C)C=1C=C(NC=2C=C(C(=O)[O-])C=CC2)C=C(C1O)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 1.70 g (0.005 mole) of 3-(3,5-di-tertiary-butyl-4-hydroxyanilino)benzoic acid (prepared in Example 13) and 50 ml of hot isopropyl alcohol was filtered to remove a small amount of insoluble material. The resulting solution was deoxygenated with a stream of nitrogen gas. Uner a nitrogen atmosphere, a solution of 0.44 g (0.005 mole) of morpholine in 1.5 ml of isopropyl alcohol was added with rapid stirring. Evaporation provided a solid which was recrystallized from a mixture of isopropyl alcohol and isopropyl ether to give solid morpholinium-3-(3,5-di-tertiary-butyl-4-hydroxyanilino)benzoate, m.p. 147°-150° C. Analysis: Calculated for C21H27NO3C4H9NO: % C, 70.1; % H, 8.5; % N, 6.5; Found: % C, 9.8; % H, 8.5; % N, 6.4. |
Here is a chemical reaction formula: Reactants are:m1_m2_m4_m3:C(C)(C)(C)C=1C(C(=CC(C1)=O)C(C)(C)C)=O;m1_m2_m4_m3:NC1=CC=C(C=C1)CCC(=O)O;m1_m2_m4_m3:B(F)(F)F.CCOCC, Reagents are:m1_m2_m4_m3:O1CCCC1, and Products are 0:C(C)(C)(C)C=1C(C(=CC(C1)=NC1=CC=C(C=C1)CCC(=O)O)C(C)(C)C)=O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture "of 5.51 g (0.025 mole) of 2,6-di-tertiary-butyl-p-benzoquinone, 4.54 g (0.027 mole) of 3-(4-aminophenyl)propionic acid, 50 ml of tetrahydrofuran and 0.25 ml of boron trifluoride etherate was heated on a steam cone under a slow stream of nitrogen for two hours. The resulting solid was triturated with hexane, collected, rinsed with hexane and recrystallized from a mixture of ethyl acetate and hexane to give 5.1 g yellow 3-[4-(2,6-di-tertiary-butylcyclohexadienon-4-ylideneamino)phenyl]propionic acid, m.p. 165°-167° C. Analysis: Calculated for C23H29NO3 : % C, 75.2; % H, 8.0; % N, 3.8; Found % C, 74.8; % H, 7.9; % N, 3.7. |
Here is a chemical reaction formula: Reactants are:m3:[H][H];m1_m2_m4:C(C)(C)(C)C=1C(C(=CC(C1)=NC1=CC=C(C=C1)CCC(=O)O)C(C)(C)C)=O;m1_m2_m4:C(C)O, Reagents are:m5:CCCCCC;m1_m2_m4:[Pd], and Products are 0:C(C)(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)NC1=CC=C(C=C1)CCC(=O)O, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 4.0 g of 3-[4-(2,6-di-tertiary-butylcyclohexadienon-4-ylideneamino)phenyl]propionic acid, 200 ml of ethanol of 0.1 g of 10% palladium on charcoal catalyst was placed on a Paar apparatus. Hydrogen uptake was complete after 30 minutes. Under a nitrogen atmosphere, the reaction mixture was filtered to remove catalyst. The filtrate was evaporated to give an oil which was coevaporated with hexane to remove all traces of ethanol and then triturated with hexane to give a light orange crystalline solid. This solid was recrystallized from a mixture of ethanol and water to give 3.1 g 3-[N-(3,5-di-tertiary-butyl-4-hydroxyphenyl)-4-aminophenyl]propionic acid, m.p. 140°-142° C. Analysis: Calculated for C23H31NO3 : % C, 74.8; % H, 8.5; % N, 3.8; Found: % C, 74.7; % H, 8.3; % N, 3.9. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3:C(C)(C)(C)C=1C(C(=CC(C1)=NC=1C=C(OCC(=O)O)C=CC1)C(C)(C)C)=O;m1_m2_m3:C(C)O, Reagents are:m1_m2_m3:[Pd];m4:C1=CC=CC=C1, and Products are 0:C(C)(C)(C)C=1C=C(NC=2C=C(OCC(=O)O)C=CC2)C=C(C1O)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5.0 g of 3-(2,6-di-tertiary-butylcyclohexadienon-4-ylideneamino)phenoxyacetic acid, 250 ml of ethanol and 10 mg of 5% palladium on charcoal catalyst was placed on a Paar apparatus. Hydrogenation was complete after five hours. The reaction mixture was filtered to remove the catalyst and the filtrate was evaporated to give a thick brown oil. The oil was dissolved in 20 ml of benzene, filtered, diluted with 20 ml of cyclohexane and 10 ml of hexane, and chilled to give 1.4 g of light tan crystalline 3-(3,5-di-tertiary-butyl-4-hydroxyanilino)phenoxyacetic acid, m.p. 127°-127.5° C. Analysis: Calculated for C22H29NO4 ; % C, 71.1; % H, 7.9; % N, 3.8; Found: % C, 70.3; % H, 7.6; % N, 3.7. |
Here is a chemical reaction formula: Reactants are:m1_m4_m2_m3:C(C)(C)(C)C=1C(C(=CC(C1)=NC1=CC=C(C=CC(=O)O)C=C1)C(C)(C)C)=O;m1_m4_m2_m3:Cl, Reagents are:m1_m4_m2_m3:[Zn];m1_m4_m2_m3:CO, and Products are 0:C(C)(C)(C)C=1C=C(NC2=CC=C(C=CC(=O)O)C=C2)C=C(C1O)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 2.0 g of 4-(2,6-di-tertiary-butylcyclohexadienon-4-ylideneamino)cinnamic acid, 100 ml of methanol, 0.5 ml of concentrated hydrochloric acid and 2 g of zinc powder was stirred for ten minutes. The mixture was filtered and the filtrate was evaporated to give a yellow gummy solid. This material was recrystallized from a mixture of 15 ml of benzene, 4 ml of hexane and 2 ml of cyclohexane to give 0.4 g of yellow granular 4-(3,5-di-tertiary-butyl-4-hydroxyanilino)cinnamic acid, m.p. 199°-200° C. Analysis: Calculated for C23H29NO3 2/3C6H6 : % C, 77.4; % H, 7.9; % N, 3.3; Found: % C, 77.2; % H, 7.8; % N, 3.3. |
Here is a chemical reaction formula: Reactants are:m3:[H][H];m1_m2_m4:C(C)(C)(C)C=1C(C(=CC(C1)=NC=1C=C(C(=O)O)C=CC1O)C(C)(C)C)=O;m1_m2_m4:C(C)O, Reagents are:m1_m2_m4:O1CCCC1, and Products are 0:C(C)(C)(C)C=1C=C(NC=2C=C(C(=O)O)C=CC2O)C=C(C1O)C(C)(C)C, please give me the reaction condition of this formula. | The condition of this chemical reaction is: A mixture of 5.0 g of 3-(2,6-di-tertiary-butylcyclohexadienon-4-ylideneamino)-4-hydroxybenzoic acid, 0.05 g of 5% palaldium on charcoal catalyst, 250 ml of ethanol and 50 ml of tetrahydrofuran was placed on a Paar apparatus. Hydrogen uptake was complete in about 10 minutes. The reaction mixture was filtered to remove catalyst. The filtrate was evaporated to give a tan solid which was recrystallized from a mixture of 40 ml of ethanol and 15 ml of water to give 3.2 g of reddish tan granular 3-(3,5-di-tertiary-butyl-4-hydroxyanilino)-4-hydroxybenzoic acid, m.p. 254.5°-255° C. (dec). Analysis: Calculated for C21H27NO4 : % C, 70.6; % H, 7.6; % N, 3.9; Found: % C, 71.0; % H, 7.6; % N, 4.1. |
Here is a chemical reaction formula: Reactants are:m1_m2_m3_m4_m5:[OH-].[Na+];m1_m2_m3_m4_m5:BrC(CCCCC)Br;m1_m2_m3_m4_m5:ClC=1C=C(C(=O)C2=CC=CC=C2)C=CC1O, Reagents are:m1_m2_m3_m4_m5:[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC;m1_m2_m3_m4_m5:C(Cl)Cl, and Products are 0:BrCCCCCCOC1=C(C=C(C(=O)C2=CC=CC=C2)C=C1)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 100 ml of a 10 percent aqueous sodium hydroxide solution are added to a solution of 34.5 g of dibromohexane, 9.9 g of 3-chloro-4-hydroxybenzophenone and 1.6 g of tetrabutylammonium bromide in 100 ml of methylene chloride. The heterogeneous mixture is stirred at room temperature overnight. The organic phase is separated, dried over sodium sulfate and evaporated. By chromatography of the residue on silica gel with hexane/ethyl acetate 7:3, there is obtained 4-[(6-bromohexyl)oxy]-3-chlorobenzophenone, m.p. 58° C. |
Here is a chemical reaction formula: Reactants are:m2_m3:[Cl-].[Al+3].[Cl-].[Cl-];m2_m3:CC1=CC=C(C=C1)C1=CC=CC=C1;m1:[N+](=O)([O-])C1=CC=CC=C1;m4:ClC=1C=C(C(=O)Cl)C=CC1Cl, Reagents are:m5:O, and Products are 0:CC1=CC=C(C=C1)C1=CC=C(C=C1)C(=O)C1=CC(=C(C=C1)Cl)Cl, please give me the reaction condition of this formula. | The condition of this chemical reaction is: 35 ml of nitrobenzene are cooled in an ice-bath and then treated in succession with 5.2 g of aluminum chloride and 5.0 g of 4-methylbiphenyl. The mixture is brought to room temperature and then treated with 7.7 g of 3,4-dichlorobenzoyl chloride. The mixture is stirred at room temperature, poured into water and extracted with methylene chloride. The extracts are washed with 2N hydrochloric acid and water, dried over magnesium sulfate and evaporated. The residue is chromatographed on silica gel with toluene/ethyl acetate 9:1. 3,4-Dichlorophenyl 4'-methyl-4-biphenylyl ketone is obtained. |