INSTRUCTION
stringlengths 285
6.82k
| RESPONSE
stringlengths 44
24.5k
|
|---|---|
Here is a chemical reaction formula: Reactants are m1_m3_m2:C1(=CC=CC=C1)SCN1S(N(C(C1=O)CCC)C)(=O)=O, amount is: 0.0 ;m1_m3_m2:S(=O)(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCN1S(N(C(C1=O)CCC)C)(=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-phenylthiomethyl-4-propyl-5-methyl-l,2,5-thiadiazolidin-3-one 1,1-dioxide (8.4 g) in 150 ml of methylene chloride was added sulfuryl chloride (3.22 ml) and the mixture was stirred for 3 hours at room temperature. The mixture was concentrated in vacuo and the residue triturated in hexane (150 ml) for 2 hours. The solvent was concentrated in vacuo and the residue was purified by flash chromatography (silica gel) to afford 5.7 g of 2-chloromethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1dioxide (Formula II: R1 =H; R2 =propyl; R3 =CH3 ; X'=Cl) as an oil. |
Here is a chemical reaction formula: Reactants are m3:CI, amount is: 0.0 ;m1_m4_m2_m5:CC(C)([O-])C.[K+], amount is: 0.0 ;m1_m4_m2_m5:C1(=CC=CC=C1)CN1S(NC(C1=O)C(C)C)(=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4_m2_m5:C1CCOC1, amount is: 0.0 MOLE;m1_m4_m2_m5:C1CCOC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)CN1S(N(C(C1=O)C(C)C)C)(=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of potassium t-butoxide (3.53 g, 29 mmol) in THF was added to a solution of 2-phenylmethyl-4-isopropyl-1, 2,5-thiadiazolidin-3-one 1,1-dioxide (7.7 g, 29 retool) in THF at 0° C. and the mixture was stirred at this temperature for 1 hour. To the mixture was added methyl iodide (20.38 g, 0.143 mol) and the resulting mixture was allowed to stir at room temperature for 2.5 hours. The resulting mixture was quenched with brine, extracted with ether, and the organic layer was washed with brine. The organic layer was dried, concentrated in vacuo, and the residue was purified by flash chromatography to afford 7.1 g (88%) of 2-phenylmethyl-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula XI: R1 =H; R2 =isopropyl; R3 =CH3) as a solid, m.p. 52.5°-54° C. |
Here is a chemical reaction formula: Reactants are m3_m8_m4:Cl.COC(C(CCC)N)=O, amount is: 0.0 ;m3_m8_m4:C(C)N(CC)CC, amount is: 0.0 ;m5_m6:Cl, amount is: 0.0 ;m5_m6:[Cl-].[Na+], amount is: 0.0 MOLE;m1_m7_m2:ClS(=O)(=O)N=C=O, amount is: 0.0 ;m1_m7_m2:C(C1=CC=CC=C1)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m8_m4:C(Cl)Cl, amount is: 0.0 ;m1_m7_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(C(CCC)NS(=O)(=O)NC(=O)OCC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 14.72 ml (0.17 mol) of chlorosulfonyl isocyanate in 400 ml of methylene chloride was added 5 benzyl alcohol (17.69 ml, 0.17 mol) at 0-5° C. After stirring the above solution for 1.5 hours at this temperature, a solution of 31.24 g (0. 186 mol) of 2-amino-pentanoic acid methyl ester hydrochloride in 1100 ml of methylene chloride containing triethylamine (51.08 g, 0.5 mol) was added at 0°-5° C., and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 600 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride/ethyl acetate (4:1) and the combined organic layer was washed with brine, dried and concentrated in vacuo to yield 47.7 g (82%) of 2-(N-carbobenzyloxyamino-sulfonyl) aminopentanoic acid methyl ester (Formula XIV: R=CH3 ; R1 =H; R2 =propyl; R3 =H) as a solid, m.p. 76°-78° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(=O)(OCC1=CC=CC=C1)NS(=O)(=O)NC(C(=O)O)CCC, amount is: 0.0 ;m1_m2_m3:CO, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m2_m3:[Pd], amount is: 0.0 .Products are 0:COC(C(CCC)NS(=O)(=O)NC(=O)OCC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-(N-carbobenzyloxyaminosulfonyl)aminopentanoic acid (46.7 g) , methanol (350 mL) and 10% palladium on carbon (3.0 g) was hydrogenated at 55 psi for about 2 hours. The catalyst was removed by filtration through CELITE®, the solvent was removed in vacuo and the residue was purified by column chromatography on silica eluting with 50% ethyl acetate/hexane to afford 25.6 g (90%) of 2-(aminosulfonylamino) pentanoic acid methyl ester (Formula XIV: R=CH3 ; R1 =H; R2 =propyl; R3 =H), m.p. 63°-64° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:COC(C(CCC)NS(=O)(=O)N)=O, amount is: 0.0 ;m1_m3_m2_m4:C[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:CO, amount is: 0.0 ;m1_m3_m2_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(CC)C1C(NS(N1)(=O)=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-(aminosulfonylamino)pentanoic acid methyl ester (24.6 g; 0.117 retool) in methanol (150 ml) was added to a solution of sodium methoxide (8.86 g, from 3.77 g of Na) in 150 ml of methanol and the resulting reaction mixture was refluxed for 18 hours. The mixture was cooled, neutralized with BIO-RAD® 50W-X8 H+ ion exchange resin, and filtered. The filtrate was concentrated in vacuo to yield an oil which was crystallized from methanol/hexane to afford 4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula IV: R1 =H; R2 =propyl; R3 =H). |
Here is a chemical reaction formula: Reactants are m3:C(C)I, amount is: 0.0 ;m1_m2_m4:CC(C)([O-])C.[K+], amount is: 0.0 ;m1_m2_m4:C1(=CC=CC=C1)CN1S(NC(C1=O)CCC)(=O)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:[Cl-].[Na+].O, amount is: 0.0 MOLE;m1_m2_m4:C1CCOC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)CN1S(N(C(C1=O)CCC)CC)(=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Potassium t-butoxide (2 . 3 g, 20.5 mmol) was added to a solution of 2-phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1, 1-dioxide (5 g, 18.6 mmol) in 100 ml of THF at 0° C. and the mixture was stirred at this temperature for 1 hour. To the mixture was added ethyl iodide (11.64 g, 74.6 mmol) and the resulting mixture was allowed to stir at room temperature for 40 hours. The resulting mixture was diluted with brine, extracted with ethyl acetate (150 ml) and the organic layer was washed with brine. The organic layer was dried, concentrated in vacuo, and the residue was purified by flash chromatography to afford 5.27 g of 2-phenylmethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula XI: R1 =H; R2 =propyl; R3 =ethyl) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C1(=CC=CC=C1)SCN1S(N(C(C1=O)CCC)CC)(=O)=O, amount is: 0.0 ;m1_m2_m3:S(=O)(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCN1S(N(C(C1=O)CCC)CC)(=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-phenylthiomethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1, 1-dioxide (3.97 g) and sulfuryl chloride (1.47 ml) in 80 ml of methylene chloride was stirred for 3 hours at room temperature. The mixture was concentrated in vacuo and the residue triturated in hexane. The solvent was concentrated in vacuo and the residue was purified by flash chromatography (silica gel) to afford 2.4 g (77%) of 2-chloromethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula II: R1 =H; R2 =propyl; R3 =ethyl; X'=Cl) as an oil. |
Here is a chemical reaction formula: Reactants are m4:CI, amount is: 0.0 ;m3:CI, amount is: 0.0 ;m1_m5_m2:C(C)(C)(C)OC(=O)N(C)CC(=O)O, amount is: 0.0 ;m1_m5_m2:N12CCCCCC2=NCCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5_m2:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(CN(C)C(=O)OC(C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of N-t-butoxycarbonyl-sarcosine (50 g; 0.264 mol) in 700 ml of benzene was added 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU; 40.19 g, 0.264 mol) in one portion. To the above clear solution was added 74.84 g (0.528 mol) of methyl iodide in one portion and the resulting clear solution was allowed to reflux for 7 hours. After adding additional methyl iodide (16 ml), the reaction mixture was refluxed with stirring, cooled to room temperature, and stirred overnight. The reaction mixture was filtered, the residue washed with ether, and the combined filtrate was washed with water, saturated sodium bicarbonate solution, and brine. The resulting organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 46.38 g (86.4%) of N-t-butoxycarbonyl-sarcosine methyl ester as a yellow oil. |
Here is a chemical reaction formula: Reactants are m1_m2:COC(C(N(C)S(=O)(=O)NC(=O)OCC1=CC=CC=C1)CCC(C)C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:CO, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:COC(C(N(C)S(=O)(=O)N)CCC(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (N-carbobenzyloxyaminosulfonyl)-2-(3-methylbutyl)sarcosine methyl ester (20.6 g, 53.17 mmol) in 200 ml of methanol under nitrogen was cooled to 0° C. and 1.5 g of 10% Pd/C was added. The mixture was placed into a Parr apparatus and hydrogenated for 3.5 hours. The catalyst was removed on a pad of CELITE® and the filtrate was concentrated in vacuo to afford 13.24 g (98.6%) of N-(aminosulfonyl)-2-(3-methylbutyl)sarcosine methyl ester (Formula VII: R=CH3 ; R1 =H; R2 =(CH2)2CH(CH3)2 ; R3 =CH3) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m2:C1(=CC=CC=C1)SCN1S(N(C(C1=O)CCC(C)C)C)(=O)=O, amount is: 0.0 ;m1_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:ClCN1S(N(C(C1=O)CCC(C)C)C)(=O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-phenylthiomethyl-4- (3-methylbutyl) -5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (8.15 g, 24.66 mmol) in 200 ml of methylene chloride was added in one portion under nitrogen sulfuryl chloride (2.36 ml, 29.6 mmol) and the mixture was stirred for 3.5 hours at room temperature. The mixture was concentrated in vacuo and the residue was triturated in hexane to afford 4.64 g (70%) of 2-chloromethyl-4- (3methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula II: R1 =H; R2 =(CH2)2CH(CH3)2 ; R3 =CH3 ; X'=Cl) as a solid, m.p. 59°-60° C. |
Here is a chemical reaction formula: Reactants are m3_m7_m8:Cl.COC(=O)C1NCCCC1, amount is: 0.0 ;m1_m6_m2:ClS(=O)(=O)N=C=O, amount is: 0.0 ;m1_m6_m2:C1(=CC=CC=C1)CO, amount is: 0.0 ;m4_m5:Cl, amount is: 0.0 ;m4_m5:[Cl-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m7_m8:C(Cl)Cl, amount is: 0.0 ;m3_m7_m8:C(C)N(CC)CC, amount is: 0.0 ;m1_m6_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC(=O)C1N(CCCC1)S(=O)(=O)NC(=O)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 7.36 ml (85 mmol) of chlorosulfonyl isocyanate in 180 ml of methylene chloride was added phenylmethanol (8.82 ml, 85 mmol) at 0° C. over a period of 35 minutes. After stirring the above solution for 2 hours at this temperature, a solution of 16.65 g (93 mmol) of 2-piperidinecarboxylic acid methyl ester hydrochloride in methylene chloride (500 ml) containing triethylamine (35.3 ml) was added at 0°-5° C. and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 600 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride (2×200 ml) and the combined organic layer was washed with brine, dried and concentrated in vacuo to yield 31 g of N -(carbobenzyloxyaminosulfonyl)-2-piperidinecarboxylic acid methyl ester(Formula XIV: R=CH3 ; R1 =H; R2 and R3 together=--(CH2)4 --) as a solid. |
Here is a chemical reaction formula: Reactants are m1_m2:COC(=O)C1N(CCCC1)S(=O)(=O)NC(=O)OCC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:CO, amount is: 0.0 ,Catalysts are m3:[Pd], amount is: 0.0 .Products are 0:COC(=O)C1N(CCCC1)S(=O)(=O)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of N-(carbobenzyloxyaminosulfonyl)-2-piperidine-carboxylic acid methyl ester (29.8 g) in methanol (300 ml) under nitrogen was cooled to 0° C. and 1.8 g of 10% Pd/C was added. The mixture was placed into a Parr Apparatus and hydrogenated for 2 hours at 55 psi. The catalyst was removed on a pad of CELITE® and the filtrate was concentrated in vacuo and purified by flash silica gel chromatography (35-40% ethyl acetate/hexane) to afford 17 g (90%) of N-(aminosulfonyl)-2-piperidinecarboxylic acid methyl ester (Formula VII: R=CH3 ; R1 =H; R2 and R3 together=--(CH2)4 --) as a solid, m.p. 72°-74° C. |
Here is a chemical reaction formula: Reactants are m1_m6_m2:ClS(=O)(=O)N=C=O, amount is: 0.0 ;m1_m6_m2:C1(=CC=CC=C1)CO, amount is: 0.0 ;m4_m5:Cl, amount is: 0.0 ;m4_m5:[Cl-].[Na+], amount is: 0.0 MOLE;m3_m7_m8:Cl.COC([C@H]1NCCC1)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m2:C(Cl)Cl, amount is: 0.0 ;m3_m7_m8:C(Cl)Cl, amount is: 0.0 ;m3_m7_m8:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC([C@H]1N(CCC1)S(=O)(=O)NC(=O)OCC1=CC=CC=C1)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 7.36 ml (84.8 mmol) of chlorosulfonyl isocyanate in 180 ml of methylene chloride was added phenylmethanol (8.82 ml, 84.9 mmol) at 0° C. over a period of 35 minutes. After stirring the above solution for 2 hours at this temperature, a solution of 15.54 g (93.28 mmol) of L-proline methyl ester hydrochloride in 500 ml of methylene chloride containing triethylamine (35.5 ml) was added at 0°-5° C., and the resulting mixture was stirred overnight allowing the mixture to warm to room temperature. The reaction mixture was poured into 600 ml of 10% aq. HCl solution, saturated with sodium chloride, and the organic layer was separated. The aqueous layer was extracted with methylene chloride (2×200 ml) and the combined organic layer was washed with brine, dried and concentrated in vacuo to yield 31 g of N-(carbobenzyloxyaminosulfonyl)-L-proline methyl ester (Formula XIV: R=CH3 ; R1 =H; R2 and R3 together=--(CH2)3 --) as an oil. |
Here is a chemical reaction formula: Reactants are m1:S1(N2C(C(N1)=O)CCC2)(=O)=O, amount is: 0.0 ;m2_m4:C1(=CC=CC=C1)SCCl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:C1(=CC=CC=C1)C, amount is: 0.0 ,Catalysts are m2_m4:[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 .Products are 0:C1(=CC=CC=C1)SCN1C(C2N(S1(=O)=O)CCC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3(2H)-one 1,1-dioxide (5.0 g, 28.4 mmol) suspended in 150 ml of toluene was added phenylthiomethyl chloride (6.76 g, 42.6 mmol) and tetrabutylammonium bromide (0.91 g) . The resulting mixture was refluxed for 6 hours, cooled, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (25-30% ethyl acetate in hexane) to afford 5.58 g (66%) of 2-phenylthiomethyl-tetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3(2H)_-one 1,1-dioxide (Formula VI: R1 =H; R2 and R3 together=--(CH2)3 --) as a solid, m.p. 90.5°-91.5° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C1(=CC=CC=C1)SCN1C(C2N(S1(=O)=O)CCC2)=O, amount is: 0.0 ;m1_m3_m2:S(=O)(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCN1C(C2N(S1(=O)=O)CCC2)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 2-phenylthiomethyltetrahydropyrrolo[1,2-b]-1,2,5-thiadiazol-3 (2H) -one 1,1-dioxide (5 g) in 130 ml of methylene chloride was added sulfuryl chloride (2.02 ml) and the mixture was stirred for 2 hours at room temperature. The mixture was concentrated in vacuo, the residue triturated in hexane (2×, 150 ml, 75 ml) with stirring, the solvent decanted, and the resulting solid filtered and dried to afford 2.96 g (92%) of 2-chloromethyl-tetrahydropyrrolo [1,2-b]-1,2,5-thiadiazol-3 (2H) -one 1,1-dioxide (Formula II: X'=Cl; R1 =H; R2 and R3 together=--(CH2)3 --)as a solid, m.p. 46.5°-47.5° C. |
Here is a chemical reaction formula: Reactants are m3:C(C=C)Br, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ;m1_m4:FC(C=1C=C(C=C(C1)C(F)(F)F)COC[C@@H](NC(=O)OC(C)(C)C)C1=CC=CC=C1)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CN(C)C=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC(C=1C=C(C=C(C1)C(F)(F)F)COC[C@@H](N(CC=C)C(=O)OC(C)(C)C)C1=CC=CC=C1)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (S)-2-((3,5-Bis(trifluoromethyl)phenyl)methyloxy)-1-phenyl-1-(N-t-butoxycarbonylamino)ethane (1.1g, Example 2b) was dissolved in 20ml anhydrous DMF and sodium hydride (0.085g) was added. The reaction mixture was stirred for 20 min and allyl bromide (0.300g) added and stirred for a further 16h. The reaction was quenched by the addition of water (30ml) and poured into 100ml ethyl acetate. The organic layer was washed with water (3×20ml), brine and dried (MgSO4). The solvent was removed in vacuo and the residue chromatographed on silica eluting with 10% Ethyl acetate/hexane to give (S)-2-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-1-phenyl-1-(N-t-butoxycarbonyl-N-allylamino)ethane as a colourless oil 0.980g. m/z=504 (M+H). |
Here is a chemical reaction formula: Reactants are m3_m4:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(S1)=S)=O, amount is: 0.0 ;m1_m2_m6_m5:Cl.CNO, amount is: 0.0 ;m1_m2_m6_m5:C([O-])([O-])=O.[Ba+2], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m4:C(C)O, amount is: 0.0 ;m1_m2_m6_m5:O, amount is: 0.0 ;m1_m2_m6_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(S1)NCO)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-methylhydroxylamine hydrochloride (12.52 g, 0.15 mole), barium carbonate (14.8 g, 0.075 mole), ethanol (50 mL), and water (50 mL) is stirred at room temperature for ten minutes. 5-[(3,5-bis (1,1-dimethylethyl)-4-hydroxyphenyl)methylene]-2-thioxo-4-thiazolidinone (see Ikuo Katsumi et al Chem. Pharm. Bull., 34(4), 1619-1627 (1986)) (17.5 g, 0.05 mole) and ethanol (600 mL) are added to it and the resulting mixture is stirred and refluxed for 8 hours. The reaction mixture is then cooled, filtered, and the solvent is removed at 45° C. under reduced pressure. The residue is treated with ice-water and the resulting solid is separated by filtration, washed with water and extracted with methylene chloride. The organic layer is dried and concentrated to give 19 g of a residue. The residue is flash chromatographed over silica gel (214 g), eluting first with methylene chloride and then with methylene chloride-methanol (9:1) to give 11.5 g of the pure product. It is recrystallized from methanol-ethyl acetate, to give 8.6 g (48%) of 5-[[2,6-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-(hydroxymethylamino)-4(5H)-thiazolone,(Z)-, mp 199°-200° C. (dec). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(S1)NCOC)=O, amount is: 0.0 ;m1_m3_m2:Cl, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:Cl.CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(S1)NCOC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 5-[(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-(methoxymethylamino)-4(5H)-thiazolone (8.3 g, 0,022 mole) in 50 mL methylene chloride is treated with ethereal hydrogen chloride to give 9.1 g (quantitative yield) of pure product, mp 177°-179° C. It is recrystallized from methylene chloride-methanol-ether to give 6.0 g (66%) of analytically pure 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-(methoxymethylamino)-4(SH)-thiazolone, monohydrochloride, (Z)-, mp 177°-179° C. |
Here is a chemical reaction formula: Reactants are m3:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(S1)SC)=O, amount is: 0.0 ;m1_m2_m4:NCC(=O)O, amount is: 0.0 ;m1_m2_m4:CC(C)([O-])C.[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(S1)=NCC(=O)O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of glycine (2.25 g, 0.03 mole), potassium-t-butoxide (2.81 g, 0.025 mole), and ethanol (700 mL) is stirred at room temperature for 15 minutes. 5-[(3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl)methylene]-2-(methylthio)-4(5H)-thiazolone (7.27 g, 0.02 mole) is added to it and the mixture is refluxed with stirring for 20 hours. The mixture is then filtered and the solvent removed at 40° C. under reduced pressure. The residue is treated with ice-water, acidified with 1N aqueous hydrochloric acid and extracted with ether. The organic layer is washed with water, dried, and the solvent removed to give 7.75 g of a solid. The crude solid is recrystallized from tetrahydrofuran-ether to give 2.95 g (38%) of pure N-[5-[3,5-[bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4-oxo-2-thiazolidinylidene]glycine, (Z)-, mp 260° C. (dec). |
Here is a chemical reaction formula: Reactants are m1_m2_m3:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(S1)SC)=O, amount is: 0.0 ;m1_m2_m3:NNC(=S)N, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(S1)=NNC(N)=S)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 5-[(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-(methylthio)-4(5H)-thiazolone (6.13 g, 0.0169 mole) and thiosemicarbazide (1.53 g, 0.0169 mole) in ethanol (300 mL) is refluxed with stirring for 7 hours. After standing overnight at room temperature, the product is separated by filtration, washed with ethanol to give 5.78 g of a solid. It is recrystallized from DMF-methanol to give 3.4 g (47%) of pure 2-[5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4-oxo-2-thiazolidinylidene]hydrazinecarbothiamide, (Z)-, mp 200°-202° C. |
Here is a chemical reaction formula: Reactants are m3:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(O1)SC)=O, amount is: 0.0 ;m1_m4:N#CN, amount is: 0.0 ;m2:CC(C)([O-])C.[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(C)O, amount is: 0.0 ;m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(O1)NC#N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.38 g (0.0090 mole) of cyanamide in 50 mL of ethanol is cooled in ice and treated in small portions with 0.93 g (0.0083 mole) of potassium tert-butoxide. After stirring for 15 minutes, 2.6 g (0.0075 mole) of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-(methylthio)-4(5H)-oxazolone is added, followed by an additional 25 mL of ethanol. The mixture is stirred at reflux for 3 hours, then cooled to allow precipitation of the potassium salt of the product. The salt is filtered, washed several times with ether, suspended in 100 mL of cold water, and acidified with 1.0 mL of acetic acid. The mixture is stirred for 30 minutes and extracted with ethyl acetate (4×75 mL). The combined organic layers are washed with brine (2×150 mL), dried (anhydrous sodium sulfate), and evaporated to yield 1.0 g (38%) of the nitrile product, [5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4,5-dihydro-4-oxo-2-oxazolyl]cyanamide. A sample recrystallized from hexane:ethyl acetate had mp 220° C. dec. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m1_m2_m3_m5:C(C)(C)(C)C=1C=C(C=O)C=C(C1O)C(C)(C)C, amount is: 0.0 ;m1_m2_m3_m5:N1C(=S)NC(=O)C1, amount is: 0.0 ;m1_m2_m3_m5:C(C)(=O)[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(N1)=S)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (30.0 g, 128 mmols), 2-thiohydantoin (14.8 g, 128 mmols), and sodium acetate (36 g) in acetic acid (200 ml) is stirred under nitrogen and heated to reflux. After 24 hours the mixture is allowed to cool, and is stirred into water (2 L). After an hour the product is filtered off, washed three times with water, and dried. Recrystallization from acetonitrile gave the 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-thioxo-4-imidazolidinone (24.6 g), mp 278°-279° C. (dec). |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:C(C)(C)(C)C=1C=C(C=O)C=C(C1O)C(C)(C)C, amount is: 0.0 ;m1_m2_m3_m5:CN1C(NC(C1)=O)=S, amount is: 0.0 ;m1_m2_m3_m5:NCCC(=O)O, amount is: 0.0 ;m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(N1C)=S)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 3,5-di-tert-butyl-4-hydroxybenzaldehyde (19.0 g, 81 mmols), 1-methyl-2-thioxo-4imidazolidinone (10.6 g, 81 mmols) and beta-alanine (4.7 g, 53 mmols) in acetic acid (150 ml) is stirred under an inert atmosphere and heated to reflux. After 5 hours the mixture is allowed to cool, and is stirred into water (1.5 L). After an hour the product is filtered off, washed three times with water, and dried. Recrystallization from acetonitrile gave the 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1-methyl-2-thioxo-4-imidazolidinone (17.5 g), mp 242°-244° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:IC, amount is: 0.0 ;m1_m2_m3_m4:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(NC(N1C)=S)=O, amount is: 0.0 ;m1_m2_m3_m4:C(C)(C)N(CC)C(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ;m1_m2_m3_m4:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(N1C)SC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Iodomethane (1.2 mL, 19 mmols) is added to a stirred suspension of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1-methyl-2-thioxo-4-imidazolidinone (4.0 g, 12 mmols) and diisopropylethylamine (2.4 mL, 14 mmols) in ethanol (50 ml) and the mixture is stirred under an inert atmosphere at room temperature. After 18 hours the mixture is stirred in water (300 mL) for an hour and the product is filtered off, washed three times with water, and dried. Recrystallization from ethyl acetate gave the pure 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1,5-dihydro-1-methyl-2-(methylthio)-4H-imidazol-4-one (3.0 g), mp 177°-179° C., retaining 0.25 equivalents of solvent of crystallization. |
Here is a chemical reaction formula: Reactants are m4:P(O)(O)(O)=O, amount is: 0.0 MOLE;m1_m2_m3_m5:N#CN, amount is: 0.0 ;m1_m2_m3_m5:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(N1C)SC)=O, amount is: 0.0 ;m1_m2_m3_m5:CC(C)([O-])C.[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:O, amount is: 0.0 ;m1_m2_m3_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(N1C)NC#N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Cyanamide (0.2 g, 4.8 mmols) is added to a solution of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-1,5-dihydro-1-methyl-2-(methylthio)-4H-imidazol-4-one (1.5 g, 3.9 mmols) and potassium tert-butoxide (0.5 g, 4.3 mmols) in ethanol (25 mL) and the mixture is stirred under an inert atmosphere and heated to reflux. After 2.5 hours the mixture is allowed to cool, and is then poured into water (200 mL), acidified with phosphoric acid, and stirred. After half an hour the product is filtered off, washed three times with water, and dried. Recrystallization from acetonitrile gave the 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4,5-dihydro-1-methyl-4-oxo-1H-imidazol-2-yl-cyanamide (0.7 g), mp 257°-259° C. (dec). |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m1_m2_m3_m5:Cl.NC(=N)N, amount is: 0.0 ;m1_m2_m3_m5:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(N1C)SC)=O, amount is: 0.0 ;m1_m2_m3_m5:CC(C)([O-])C.[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(N1C)NC(=N)N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Guanidine hydrochloride (1.7 g, 18 mmoles) is added to a mixture of 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene)-1,5-dihydro-1-methyl-2-(methylthio)-4-H-imidazole-4-one (3.0 g, 8 mmoles) and potassium tert-butoxide (1.5 g, 13 mmoles) in ethanol (50 mL), and stirred and heated to reflux under an inert atmosphere. After 24 hours the mixture is allowed to cool, and is poured into water (300 mL) and stirred. After half an hour the product is filtered off, rinsed three times with water and dried. Recrystallization from ethanol/DMF gave pure 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]-methylene)-4,5-dihydro-1-methyl-4-oxo-1H-imidazol-2-yl-guanidine (0.6 g), mp 288°-290° C. (dec). |
Here is a chemical reaction formula: Reactants are m4:CC(C)([O-])C.[K+], amount is: 0.0 ;m1_m2_m3:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(N1C)SC)=O, amount is: 0.0 ;m1_m2_m3:Cl.NC(=N)N, amount is: 0.0 ;m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C=C1C(N=C(N1C)NC(=N)N)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 5-[[3,5-bis(1,1-dimethylethyl)-4hydroxyphenyl]methylene]-1,5-dihydro-l-methyl-2-(methylthio)-4H-imidazol-4-one (3.0 g, 8 mmoles), guanidine hydrochloride (1.7 g, 18 mmoles) and 50 mL of ethanol is treated with potassium t-butoxide (1.5 g, 13 mmoles) and heated under reflux for 20 hours, then stirred into 400 mL of water. The precipitate is filtered off, rinsed with water, dried, and recrystallized from acetone to afford the product (1.4 g), mp 286°-287° C. (dec). A sample recrystallized from DMF/EtOH was analytically pure which is N-[5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4,5-dihydro-1-methyl-4-oxo-1H-imidazol-2-yl]guanidine, mp 288°-290° C. (dec). |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m1_m2_m3_m5:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C(C)=C1C(NC(S1)=S)=O, amount is: 0.0 ;m1_m2_m3_m5:IC, amount is: 0.0 ;m1_m2_m3_m5:C(C)(C)N(CC)C(C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC(C)(C)C=1C=C(C=C(C1O)C(C)(C)C)C(C)=C1C(N=C(S1)SC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 5-[1-[3,5-bis(1,1-dimethylethyl)-4hydroxyphenyl]ethylidene]-2-thioxo-4-thiazolidinone (1.6 g, 4 mmoles), iodomethane (0.45 mL, 7 mmoles), and diisopropylethylamine (1.1 mL, 6 mmoles) in 20 mL of ethanol is stirred under N2 at room temperature for 16 hours, then stirred into 200 mL of water. The precipitate is filtered off, rinsed with water, and dried to afford the product (1.4 g) of 5-[1-[3,5bis(1,1-dimethylethyl)-4-hydroxyphenyl]-ethylidene]-2-(methylthio)-4(5H)-thiazolone, mp 206°-209° C. A sample recrystallized from acetonitrile was analytically pure, mp 224°-226° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:C(CCC)C1=C(C(O)=CC=C1)O, amount is: 0.0 ;m1_m2_m3_m5:C(=O)([O-])[O-].[Na+].[Na+], amount is: 0.0 ;m1_m2_m3_m5:NC1=C(C(=O)OC)C=CC(=C1)C(=O)OC, amount is: 0.0 ;m4:C(=C)CC(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:CC(=O)C, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C=CC)(=O)NC1=C(C(=O)OC)C=CC(=C1)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 110 mg of butylpyrocatechol (as a polymerization inhibitor) and 180 g of dry Na2CO3 (anhydrous) are added to 167.4 g (0.8 mol) of dimethyl aminoterephthalate in 3 1 of acetone. 89 g (0.85 mol) of vinylacetyl chloride are added dropwise to this mixture at 35°-40 ° C. in the course of 20 minutes and the mixture is then boiled under reflux for 4 hours. The filtered solution is concentrated to 1 1 and the concentrate is crystallized in the cold. The crystals of dimethyl N-butenoylaminoterephthalate isolated are recrystallized once from 1.2 1 of methanol and then from a mixture of 426 ml of ethyl acetate and 344 ml of methanol. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:ClC=1C(=C(C=CC1F)NCC(=O)O)C(=O)O, amount is: 0.0 ;m1_m2_m3:C(C)(=O)[O-].[Na+], amount is: 0.0 ;m1_m2_m3:C(C)(=O)OC(C)=O, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:C(C)(=O)OC1=CN(C2=CC=C(C(=C12)Cl)F)C(C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 2.63 g of N-[3-chloro-2-(hydroxycarbonyl)-4-fluoro-phenyl]glycine and 2.63 g of sodium acetate in 25 ml of acetic anhydride was boiled under reflux for 45 minutes. The solvent was removed in a vacuum and the residue was treated with 50 ml of water. The crystals were filtered off, washed with water and dried. There were obtained 2.7 g (94%) of 3-acetoxy-1-acetyl-4-chloro-5-fluoroindole as yellow crystals with m.p. 168°-169°. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(=O)N1CC(C2=C(C(=CC=C12)F)Cl)=O, amount is: 0.0 ;m1_m2_m3:[OH-].[Na+], amount is: 0.0 ;m1_m2_m3:S(=O)(=O)(OC)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C([O-])(O)=O.[Na+], amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)N1C=C(C2=C(C(=CC=C12)F)Cl)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2 g of 1-acetyl-4-chloro-5-fluoroindolin-3-one, 2 g of powdered sodium hydroxide and 30 ml of dimethyl sulfate was stirred at room temperature for 5 hours. After the addition of 250 ml of saturated sodium bicarbonate solution the mixture was stirred overnight and subsequently filtered. The residue was filtered in 150 ml of ether and 100 ml of ethyl acetate. The solution was dried over sodium sulfate, filtered and evaporated. There were obtained 2 g (95%) of 1-acetyl-4-chloro-5-fluoro-3-methoxyindole as greenish crystals with m.p. 114°-115°. |
Here is a chemical reaction formula: Reactants are m1_m3:C(C)(=O)OC1=CN(C2=CC=C(C=C12)F)C(C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:S(O)(O)(=O)=O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)N1CC(C2=CC(=CC=C12)F)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2.2 g of 3-acetoxy-1-acetyl-5-fluoroindole were added to 20 ml of 90% sulfuric acid and, after stirring for three quarters of an hour, the reaction mixture was diluted with 100 ml of ice-water. The precipitate was filtered off, washed with water and dried. There were obtained 1.6 g (83%) of 1-acetyl-5-fluoroindolin-3-one as beige crystals with a m.p. of 143°-144°. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(=O)N1CC(C2=CC(=CC=C12)F)=O, amount is: 0.0 ;m1_m2_m3:[OH-].[Na+], amount is: 0.0 ;m1_m2_m3:S(=O)(=O)(OC)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:C([O-])(O)=O.[Na+], amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)N1C=C(C2=CC(=CC=C12)F)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 1.6 g of 1-acetyl-5-fluoroindolin-3-one, 1.9 g of powdered sodium hydroxide and 28 ml of dimethyl sulfate was stirred at room temperature for two hours. After the addition of 240 ml of saturated sodium bicarbonate solution the mixture was stirred overnight and subsequently filtered. The residue was taken up in 100 ml of ether and 100 ml of ethyl acetate. The solution was dried over sodium sulfate, filtered and evaporated. There were obtained 1.47 g (86%) of 1-acetyl-5-fluoro-3-methoxyindole as greenish crystals with m.p. 124°-125°. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)(=O)N1C=C(C2=CC(=CC=C12)F)OC, amount is: 0.0 ;m1_m2_m3:C[O-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C2C(=CNC2=CC1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.25 g of 1-acetyl-5-fluoro-3-methoxyindole and 0.35 g of sodium methylate in 23 ml of methanol was stirred at room temperature for one hour. After removal of the solvent the residue was extracted with water and ethyl acetate and the organic phase was washed with saturated sodium chloride solution and dried over sodium sulfate. The solvent was removed and the residue was distilled in a bulb-tube at a bath temperature of 200° and a pressure of 50 mbar. 0.76 g (76%) of 5-fluoro-3-methoxyindole was obtained. |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:ClC=1C=C2C=CNC2=CC1, amount is: 0.0 ;m1_m3_m2_m4:[OH-].[Na+], amount is: 0.0 ;m1_m3_m2_m4:BrCCBr, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m3_m2_m4:[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 .Products are 0:BrCCN1C=CC2=CC(=CC=C12)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1 g of 5-chloroindole in 30 ml of 1,2-dibromoethane was treated with 30 ml of 28% NaOH and 80 mg of tetrabutyl-ammonium bromide. The mixture was stirred at 50° for 3 hours. The phases were separated and the aqueous phase was extracted with toluene. The combined organic phases were washed with water and dried over sodium sulfate. The solvent was distilled off and the residue was chromatographed over 150 g of silica gel with hexane-ethyl acetate (5:1). There were obtained 1.17 g (69%) of 1-(2-bromoethyl)-5-chloroindole as white crystals with a m.p. of 71°. |
Here is a chemical reaction formula: Reactants are m2:[OH-].[Na+], amount is: 0.0 ;m1_m3:ClC1=C2C=C(NC2=CC=C1F)C(=O)OCC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C2C=C(NC2=CC=C1F)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 6.3 g of ethyl 4-chloro-5-fluoroindole-2-carboxylate in 260 ml of ethanol was treated with 130 ml of 2N sodium hydroxide solution and stirred for 3 hours. Ethanol was evaporated and the reaction solution was adjusted to pH 1 with 25% hydrochloric acid. The precipitate was washed with water and dried. There were obtained 5.3 g (96%) of crude 4-chloro-5-fluoroindole-2-carboxylic acid which was used in the next step without further purification. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:CC1=C2C(=C(NC2=CC=C1)C(=O)OCC)OC, amount is: 0.0 ;m1_m3_m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C2C(=C(NC2=CC=C1)C(=O)O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.76 g of ethyl 4-methyl-3-methoxyindole-2-carboxylate in 90 ml of ethanol was treated with 45 ml of 2N sodium hydroxide solution and stirred at room temperature for 17 hours. The alcohol was evaporated and the residue was treated with 60 ml o of 2N hydrochloric acid. The separated crystals were filtered off, washed with water and dried. There were obtained 1.2 g (78%) of 4-methyl-3-methoxyindole-2-carboxylic acid as brown crystals with m.p. 136°. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 ;m3:CC1OC1, amount is: 0.0 ;m2:ClC=1C=C2C=CNC2=CC1, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ;m6:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=C2C=CN(C2=CC1)CC(C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.4 g of sodium hydride dispersion in 60 ml of tetrahydrofuran was treated with 1.74 g of 5-chloroindole at 0° and stirred at this temperature for 1 hour. After the addition of 1.6 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with 11 ml of water. The mixture was diluted with 300 ml of ether, washed with 140 ml of water and with 70 ml of saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 60 g of silica gel with toluene-ethyl acetate (19:1). There were obtained 2.1 g (87%) of (RS)-1-(5-chloro-indol-1-yl)-propan-2-ol as a yellow oil. |
Here is a chemical reaction formula: Reactants are m2:FC=1C=C2C=CNC2=CC1, amount is: 0.0 ;m4:O, amount is: 0.0 ;m3:CC1OC1, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 MOLE;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C2C=CN(C2=CC1)CC(C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.55 g of sodium hydride dispersion in 75 ml of tetrahydrofuran was treated with 2 g of 5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 2.1 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 24 hours and subsequently treated with 5 ml of water. The mixture was diluted with ether, washed three times with 75 ml of water each time and with 70 ml of saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 60 g of silica gel with toluene-ethyl acetate (19:1). There were obtained 1.8 g (62%) of (RS)-1-(5-fluoro-indol-1-yl)-propan-2-ol as a yellow oil. |
Here is a chemical reaction formula: Reactants are m1_m5:[H-].[Na+], amount is: 0.0 ;m3:C[C@@H]1OC1, amount is: 0.0 ;m2:FC=1C=C2C=CNC2=CC1, amount is: 0.0 ;m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 ;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C2C=CN(C2=CC1)C[C@H](C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.26 g of sodium hydride dispersion in 35 ml of tetrahydrofuran was treated with 0.95 g of 5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 1 ml of (S)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with 7 ml of water. The mixture was diluted with 180 ml of ether, washed twice with 90 ml of water each time and with 50 ml of saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 28 g of silica gel with toluene-ethyl acetate (19:1). There were obtained 1.15 g (84%) of (S)-1-(5-fluoro-indol-1-yl)-propan-2-ol as a light brown oil. |
Here is a chemical reaction formula: Reactants are m1_m4:N(=[N+]=[N-])[C@@H](CN1C=CC2=CC(=CC=C12)F)C, amount is: 0.0 ;m2:C(\C=C\C(=O)O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C(C)O, amount is: 0.0 ;m5_m3:C(C)O, amount is: 0.0 ,Catalysts are m5_m3:[Pt]=O, amount is: 0.0 .Products are 0:C(\C=C\C(=O)O)(=O)O.FC=1C=C2C=CN(C2=CC1)C[C@@H](C)N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.1 g of platinum oxide in 25 ml of ethanol was stirred under a hydrogen atmosphere for half an hour and subsequently treated with a solution of 0.92 g of (R)-1-(2-azido-propyl)-5-fluoroindole in 25 ml of ethanol. The reaction mixture was stirred at room temperature for two hours. The catalyst was filtered off and washed with ethanol. The solution was evaporated and the residue was dissolved in 150 ml of ether and treated with 0.58 g (5 mmol) of fumaric acid and stirred overnight. The separated crystals were filtered off and dried. There were obtained 1.14 g (88%) of (R)-2-(5-fluoro-indol-1-yl)-1-methyl-ethylamine fumarate (1:1) as white crystals with m.p. 159°-161° (dec.) |
Here is a chemical reaction formula: Reactants are m2:FC=1C=C2C=CNC2=CC1, amount is: 0.0 ;m3:C[C@H]1OC1, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ;m6:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C2C=CN(C2=CC1)C[C@@H](C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.26 g of sodium hydride dispersion in 35 ml of tetrahydrofuran was treated with 0.95 g (7 mmol) of 5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 1 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with 7 ml of water. The mixture was diluted with 180 ml of ether, washed twice with 90 ml of water each time and with 50 ml of saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 28 g of silica gel with toluene-ethyl acetate (19:1). There were obtained 1.09 g (80%) of (R)-1-(5-fluoro-indol-1-yl)-propan-2-ol as a light brown oil. |
Here is a chemical reaction formula: Reactants are m2:ClC1=C(C=C2C=CNC2=C1)F, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE;m3:C[C@@H]1OC1, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 MOLE;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C=C2C=CN(C2=C1)C[C@H](C)O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.11 g of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.5 g of 6-chloro-5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.42 ml of (S)-methyloxirane the reaction mixture was stirred at room temperature for 85 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 25 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.54 g (79%) of (S)-1-(6-chloro-5-fluoro-indol-1-yl)-propan-2-ol as beige crystals (m.p. 99°-101°). |
Here is a chemical reaction formula: Reactants are m2:ClC1=C(C=C2C=CNC2=C1)F, amount is: 0.0 ;m3:C[C@H]1OC1, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 MOLE;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C=C2C=CN(C2=C1)C[C@@H](C)O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.11 g of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.5 g of 6-chloro-5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.42 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 85 hours and subsequently treated with is water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 25 g of silica gel with toluene/ethyl acetate (19:1). There was obtained 0.51 g (74.6%) of (R)-1-(6-chloro-5-fluoro-indol-1-yl)-propan-2-ol as white crystals (m.p. 104°-105°.) |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m2:CC1=C2C=CNC2=CC=C1, amount is: 0.0 ;m3:CC1OC1, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 MOLE;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=C2C=CN(C2=CC=C1)CC(C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.26 g of sodium hydride dispersion in 35 ml of tetrahydrofuran was treated with 0.95 g of 4-methylindole at 0° as and stirred at this temperature for 1 hour. After the addition of 1 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 25 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.86 g (62.7%) of (RS)-1-(4-methyl-indol-1-yl)-propan-2-ol as a yellow oil. |
Here is a chemical reaction formula: Reactants are m3:CC1OC1, amount is: 0.0 ;m2:BrC=1C=C2C=CNC2=CC1, amount is: 0.0 ;m4:O, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 ;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:BrC=1C=C2C=CN(C2=CC1)CC(C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.56 g of sodium hydride dispersion in 75 ml of tetrahydrofuran was treated with 2.95 g of 5-bromoindole at 0° C. and stirred at this temperature for 1 hour. After the addition of 2.1 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 60 hours and subsequently treated with 15 ml of water. The mixture was diluted with 750 ml of ether, washed twice with 250 ml of water and with 125 ml of saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 120 g of silica gel with toluene-ethyl acetate (19:1). There were obtained 3.4 g (89%) of (RS)-1-(5-bromo-indol-1-yl)-propan-2-ol as a yellow oil. |
Here is a chemical reaction formula: Reactants are m2:CC1=CC=C2C=CNC2=C1, amount is: 0.0 ;m4:O, amount is: 0.0 ;m3:CC1OC1, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ;m6:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CC1=CC=C2C=CN(C2=C1)CC(C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.28 g of sodium hydride dispersion in 40 ml of tetrahydrofuran was treated with 0.98 g of 6-methylindole at 0° and stirred at this temperature for 1 hour. After the addition of 1 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 60 hours and subsequently treated with 7 ml of water. The mixture was diluted with 370 ml of ether, washed twice with 120 ml of water and with 60 ml of saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 35 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.5 g (35%) of (RS)-1-(6-methyl-indol-1-yl)-propan-2-ol as light brown crystals with m.p. 65°-69°. |
Here is a chemical reaction formula: Reactants are m1_m5:[H-].[Na+], amount is: 0.0 ;m3:CC1OC1, amount is: 0.0 ;m2:FC1=CC=C2C=CNC2=C1, amount is: 0.0 ;m4:O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ;m6:CCOCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=CC=C2C=CN(C2=C1)CC(C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.26 g of sodium hydride dispersion in 35 ml of tetrahydrofuran was treated with 0.97 g of 6-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 1 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with 7 ml of water. The mixture was diluted with 180 ml of ether, washed twice with 90 ml of water and with 50 ml of saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 28 g of silica gel with toluene-ethyl acetate (19:1). There were obtained 1.1 g (79.3%) of (RS)-1-(6-fluoro-indol-1-yl)-propan-2-ol as a colourless oil. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:FC=1C=C2C=C(NC2=CC1F)C(=O)OCC, amount is: 0.0 ;m1_m3_m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C2C=C(NC2=CC1F)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2.06 g of ethyl 5,6-difluoroindole-2-carboxylate in 90 ml of ethanol was treated with 45 ml of 2N sodium hydroxide solution and stirred at room temperature for 17 hours. The alcohol was evaporated and the residue was treated with 50 ml of 2N hydrochloric acid. The separated crystals were filtered off, washed with water and dried. 1.78 g (98.8%) of 5,6-difluoroindole-2-carboxylic acid were obtained as brown crystals with m.p. 279°-280°. |
Here is a chemical reaction formula: Reactants are m3:C[C@H]1OC1, amount is: 0.0 ;m2:FC=1C=C2C=CNC2=CC1F, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 MOLE;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C2C=CN(C2=CC1F)C[C@@H](C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.12 g of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.5 g of 5,6-difluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.46 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 60 hours and subsequently treated with water. The mixture was diluted with ether, washed twice with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 35 g of silica gel with toluene-ethyl acetate (19:1). 0.46 g (66.5%) of (R)-1-(5,6-difluoro-indol-1-yl)-propan-2-ol was obtained as yellowish crystals with m.p. 114°-116°. |
Here is a chemical reaction formula: Reactants are m1_m5:[H-].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 MOLE;m2:FC=1C=C2C=CNC2=CC1F, amount is: 0.0 ;m3:C[C@@H]1OC1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ;m6:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC=1C=C2C=CN(C2=CC1F)C[C@H](C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.12 g of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.5 g of 5,6-difluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.46 mlof (S)-methyloxirane the reaction mixture was stirred at room temperature for 60 hours and subsequently treated with water. The mixture was diluted with ether, washed twice with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 35 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.5 g (74%) of (S)-1-(5,6-difluoro-indol-1-yl)-propan-2-ol as yellowish crystals with m.p. 116°-118°. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:FC=1C(=C2C=C(NC2=CC1)C(=O)OCC)C(F)(F)F, amount is: 0.0 ;m1_m3_m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C(=C2C=C(NC2=CC1)C(=O)O)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2.24 g of ethyl 5-fluoro-4-trifluoromethylindole-2-carboxylate in 80 ml of ethanol was treated with 40 ml of 2N sodium hydroxide solution and stirred at room temperature for 1 hour. The alcohol was evaporated and the solution was adjusted to pH 1 with 2N hydrochloric acid. The separated crystals were isolated, washed with water and dried. There were obtained 1.17 g (85%) of 5-fluoro-4-trifluoromethylindole-2-carboxylic acid as beige crystals with m.p. 204°-210°. |
Here is a chemical reaction formula: Reactants are m2:[H-].[Na+], amount is: 0.0 ;m1_m4:FC=1C(=C2C=C(NC2=CC1)C(=O)O)C(F)(F)F, amount is: 0.0 ;m3:C[C@@H]1OC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O1CCCC1, amount is: 0.0 ;m1_m4:C1(=CC=CC=C1)OC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C(=C2C=CN(C2=CC1)C[C@@H](C)O)C(F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.8 g of 5-fluoro-4-trifluoromethylindole-2-carboxylic acid in 16 ml of diphenyl ether was stirred at 260° for 4 hours and, after cooling to 0°, diluted with 16 ml of tetrahydrofuran. 122 mg of sodium hydride dispersion were added and the mixture was stirred for 1 hour. Subsequently, 0.46 ml of (S)-methyloxirane was added and the reaction mixture was stirred at room temperature for 60 hours. The mixture was extracted with diethyl ether, water and saturated sodium chloride solution and the organic phase was dried over sodium sulfate. The solvent was removed and the residue was chromatographed over 40 g of silica gel with hexane-toluene (1:1) and subsequently with toluene-ethyl acetate (15:1). There was obtained 0.3 g (35.5%) of (R)-1-(5-fluoro-4-trifluoromethyl-indol-1-yl)-propan-2-ol as light brown crystals. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:FC=1C=C2C=C(NC2=CC1C(F)(F)F)C(=O)OCC, amount is: 0.0 ;m1_m3_m2:[OH-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C2C=C(NC2=CC1C(F)(F)F)C(=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 1.85 g of ethyl 5-fluoro-6-trifluoromethylindole-2-carboxylate in 60 ml of ethanol was treated with 30 ml of 2N sodium hydroxide solution and stirred at room temperature for 1 hour. The alcohol was evaporated and the solution was adjusted to pH 1 with 2N hydrochloric acid. The separated crystals were isolated, washed with water and dried. There were obtained 1.5 g (90%) of 5-fluoro-6-trifluoromethylindole-2-carboxylic acid as brown crystals with m.p. 178°-180°. |
Here is a chemical reaction formula: Reactants are m2:[H-].[Na+], amount is: 0.0 ;m1_m4:FC=1C=C2C=C(NC2=CC1C(F)(F)F)C(=O)O, amount is: 0.0 ;m3:C[C@H]1OC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O1CCCC1, amount is: 0.0 ;m1_m4:C1(=CC=CC=C1)OC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C2C=CN(C2=CC1C(F)(F)F)C[C@@H](C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.75 g of 5-fluoro-6-trifluoromethylindole-2-carboxylic acid in 16 ml of diphenyl ether was stirred at 260° for 4 hours and, after cooling to 0°, diluted with 16 ml of tetrahydrofuran. 113 mg of sodium hydride dispersion were added and the mixture was stirred for 1 hour. Subsequently, 0.43 ml of (R)-methyloxirane was added and the reaction mixture was stirred at room temperature for 60 hours. The mixture was extracted with diethyl ether, water and saturated sodium chloride solution and the organic phase was dried over sodium sulfate. The solvent was removed and the residue was chromatographed over 40 g of silica gel with hexane-toluene (1:1) and subsequently with toluene-ethyl acetate (15:1). There was obtained 0.15 g (18.9%) of (R)-1-(5-fluoro-6-trifluoromethyl-indol-1-yl)-propan-2-ol as light brown crystals. |
Here is a chemical reaction formula: Reactants are m3:C[C@H]1OC1, amount is: 0.0 ;m2:ClC1=C2C=CNC2=CC=C1F, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 MOLE;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C2C=CN(C2=CC=C1F)C[C@@H](C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.11 g of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.5 g of 4-chloro-5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.4 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 30 g of silica gel with toluene-ethyl acetate (33:1). There was obtained 0.5 g (74.5%) of (R)-1-(4-chloro-5-fluoro-indol-1-yl)-propan-2-ol as a yellow oil. |
Here is a chemical reaction formula: Reactants are m1_m5:[H-].[Na+], amount is: 0.0 ;m3:C[C@@H]1OC1, amount is: 0.0 ;m2:ClC1=C2C=CNC2=CC=C1F, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ;m6:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC1=C2C=CN(C2=CC=C1F)C[C@H](C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.11 g of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.5 g of 4-chloro-5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.4 ml of (S)-methyloxirane the reaction mixture was stirred at s room temperature for 48 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 30 g of silica gel with toluene-ethyl acetate (33:1). There was obtained 0.53 g (78.9%) of (S)-1-(4-chloro-5-fluoro-indol-1-yl)-propan-2-ol as a yellow oil. |
Here is a chemical reaction formula: Reactants are m1_m5:[H-].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 MOLE;m2:CC=1C=C2C=CNC2=CC1, amount is: 0.0 ;m3:CC1OC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ;m6:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:CC=1C=C2C=CN(C2=CC1)CC(C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.26 g of sodium hydride dispersion in 35 ml of tetrahydrofuran was treated with 0.95 g of 5-methylindole at 0° and stirred at this temperature for 1 hour. After the addition of 1 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 30 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.86 g (62.7%) of (RS)-1-(5-methyl-indol-1-yl)-propan-2-ol as a yellow oil. |
Here is a chemical reaction formula: Reactants are m4:Cl, amount is: 0.0 MOLE;m1:[Na], amount is: 0.0 ;m2_m3_m6:ClC=1C=C(C=O)C=CC1F, amount is: 0.0 ;m2_m3_m6:N(=[N+]=[N-])CC(=O)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:CO, amount is: 0.0 ;m2_m3_m6:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=C(C=C(C(=O)OC)N=[N+]=[N-])C=CC1F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: While cooling with an ice bath 1.35 g of sodium were dissolved in 30 ml of methanol and subsequently a solution of 4.65 g of 3-chloro-4-fluorobenzaldehyde and 6.75 g of methyl azidoacetate in 10 ml of methanol were added within 20 min. The reaction mixture was stirred at room temperature for 3 hours and then neutralized with 2N HCl. The mixture was extracted with ethyl acetate, washed with water and saturated sodium chloride solution and the organic phase was dried over sodium sulfate. The solvent was removed and the residue was chromatographed over 250 g of silica gel with n-hexane-toluene 2:1. There were obtained 2.5 g (33%) of methyl 3-chloro-4-fluoro-a-azidocinnamate as yellow crystals with m.p. 72°-74°. |
Here is a chemical reaction formula: Reactants are m2_m3_m4:ClC=1C=C2C=C(NC2=CC1F)C(=O)O, amount is: 0.0 MOLE;m2_m3_m4:ClC=1C(=CC=C2C=C(NC12)C(=O)O)F, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m2_m3_m4:C1(=CC=CC=C1)OC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=C2C=CNC2=CC1F;0:ClC=1C(=CC=C2C=CNC12)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 1.92 g of an almost 1:1 mixture of 5-chloro-6-fluoro-indole-2-carboxylic acid and 7-chloro-6-fluoro-indole-2-carboxylic acid in 45 ml of diphenyl ether was stirred at 260° for 4 hours. The reaction mixture was chromatographed over 100 g of silica gel with hexane and hexane-toluene (3:1). There were obtained 0.6 g (39%) of 5-chloro-6-fluoroindole as light brown crystals with m.p. 88°-90° and 0.22 g (14%) of 7-chloro-6-fluoroindole as a dark brown oil. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m3:CC1OC1, amount is: 0.0 ;m2:ClC=1C(=CC=C2C=CNC12)F, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 MOLE;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C(=CC=C2C=CN(C12)CC(C)O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 45 mg of sodium hydride dispersion in 10 ml of tetrahydrofuran was treated with 0.2 g of 7-chloro-6-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.17 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 4 days and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 15 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.21 g (77.8%) of (RS)-1-(7-chloro-6-fluoro-indol-1-yl)-propan-2-ol as white crystals with m.p. 85°-87°. |
Here is a chemical reaction formula: Reactants are m2:ClC=1C=C2C=C(NC2=CC1)C, amount is: 0.0 ;m3:CC1OC1, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ;m6:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1C=C2C=C(N(C2=CC1)CC(C)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 75 ml of sodium hydride dispersion in 15 ml of tetrahydrofuran was treated with 0.33 g of 5-chloro-2-methylindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.28 ml of (RS)-methyloxirane the reaction mixture was stirred at room temperature for 48 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 13 g of silica gel with toluene-ethyl acetate (19:1). There was obtained 0.27 g (61.7%) of (RS)-1-(5-chloro-2-methyl-indol-1-yl)-propan-2-ol as a yellow oil. |
Here is a chemical reaction formula: Reactants are m3:C[C@H]1OC1, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ;m1_m4:C(C)C1=C(NC2=CC=C(C=C12)F)C(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O1CCCC1, amount is: 0.0 ;m1_m4:C1(=CC=CC=C1)OC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)C1=CN(C2=CC=C(C=C12)F)C[C@@H](C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 1.21 g of 3-ethyl-5-fluoroindole-2-carboxylic acid in 16 ml of diphenyl ether was stirred at 260° for 2 hours and, after cooling to 0°, diluted with 29 ml of tetrahydrofuran. 218 mg of sodium hydride dispersion were added and the mixture was stirred for one hour. Subsequently, 0.61 ml of (R)-methyloxirane was added and the reaction mixture was stirred at room temperature for 90 hours. The mixture was extracted with diethyl ether, water and saturated sodium chloride solution and the organic phase was dried over sodium sulfate. The solvent was removed and the residue was chromatographed over 120 g of silica gel with hexane-toluene (1:2) and subsequently with toluene-ethyl acetate (9:1). 0.8 g (62%) of (R)-1-(3-ethyl-5-fluoro-indol-1-yl)-propan-2-ol was obtained as pale brown crystals with m.p. 65°-67°. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m2:C(C)(C)C1=C2C=CNC2=CC=C1F, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ;m3:C[C@H]1OC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 MOLE;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(C)C1=C2C=CN(C2=CC=C1F)C[C@@H](C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.16 g of sodium hydride dispersion in 22 ml of tetrahydrofuran was treated with 0.38 g of 4-isopropyl-5-fluoroindole at 0° and stirred at this temperature for I hour. After the addition of 0.6 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 120 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 25 g of silica gel with toluene-ethyl acetate (19:1). 0.41 g (81%) of (R)-1-(4-isopropyl-5-fluoro-indol-1-yl)-propan-2-ol was obtained as a yellow oil. |
Here is a chemical reaction formula: Reactants are m2:C(C)(C)C1=C(C=C2C=CNC2=C1)F, amount is: 0.0 ;m3:C[C@H]1OC1, amount is: 0.0 ;m1_m5:[H-].[Na+], amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5:O1CCCC1, amount is: 0.0 ;m6:CCOCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)(C)C1=C(C=C2C=CN(C2=C1)C[C@@H](C)O)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.05 g of sodium hydride dispersion in 10 ml of tetrahydrofuran was treated with 0.23 g of 6-isopropyl-5-fluoroindole at 0° and stirred at this temperature for 1 hour. After the addition of 0.18 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 70 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 15 g of silica gel with toluene-ethyl acetate (19:1). 0.08 g (27%) of (R)-1-(6-isopropyl-5-fluoro-indol-1-yl)-propan-2-ol was obtained as a yellow oil. |
Here is a chemical reaction formula: Reactants are m3:C[C@H]1OC1, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ;m1_m4:ClC1=C(C=C2C(=C(NC2=C1)C(=O)O)CC)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1(=CC=CC=C1)OC1=CC=CC=C1, amount is: 0.0 ;m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C=C2C(=CN(C2=C1)C[C@@H](C)O)CC)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 1.16 g of 6-chloro-5-fluoro-3-ethyl-indole-2-carboxylic acid in 16 ml of diphenyl ether was stirred at 260° for 4 hours and, after cooling to 0°, diluted with 24 ml of tetrahydrofuran. 180 mg of sodium hydride dispersion were added and the mixture was stirred for one hour. Subsequently, 0.5 ml of (R)-methyloxirane was added and the reaction mixture was stirred at room temperature for 112 hours. The mixture was extracted with diethyl ether, water and saturated sodium chloride solution and the organic phase was dried over sodium sulfate. The solvent was removed and the residue was chromatographed over 120 g of silica gel with hexane-toluene (1:2) and subsequently with toluene-ethyl acetate (9:1). 0.97 g (79%) of (R)-1-(6-chloro-5-fluoro-3-ethylindol-1-yl)-propan-2-ol was obtained as pale brown crystals with m.p. 112°-114°. |
Here is a chemical reaction formula: Reactants are m2:[H-].[Na+], amount is: 0.0 ;m1_m4:ClC1=C2C(=C(NC2=CC=C1F)C(=O)O)CC, amount is: 0.0 ;m3:C[C@H]1OC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O1CCCC1, amount is: 0.0 ;m1_m4:C1(=CC=CC=C1)OC1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C2C(=CN(C2=CC=C1F)C[C@@H](C)O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 1.2 g of 4-chloro-5-fluoro-3-ethyl-indole-2-carboxylic acid in 16 ml of diphenyl ether was stirred at 260° for 4 hours and, after cooling to 0°, diluted with 24 ml of tetrahydrofuran. 186 mg of sodium hydride dispersion were added and the mixture was stirred for one hour. Subsequently, 0.5 ml of (R)-methyloxirane was added and the reaction mixture was stirred at room temperature for 114 hours. The mixture was extracted with diethyl ether, water and saturated sodium chloride solution and the organic phase was dried over sodium surfate. The solvent was removed and the residue was chromatographed over 120 g of silica gel with hexane-toluene (1:2) and subsequently with toluene-ethyl acetate (9:!). 102 g (80%) of (R)-1-(4-chloro-5-fluoro-3-ethylindol-1-yl)-propan-2-ol were obtained as pale brown crystals with m.p. 87°-88°. |
Here is a chemical reaction formula: Reactants are m1_m4:FC=1C=C2C(=C(NC2=CC1)C(=O)O)C, amount is: 0.0 ;m2:[H-].[Na+], amount is: 0.0 ;m3:C[C@H]1OC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1(=CC=CC=C1)OC1=CC=CC=C1, amount is: 0.0 ;m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C2C(=CN(C2=CC1)C[C@@H](C)O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 1.16 g of 5-fluoro-3-methyl-indole-2-carboxylic acid in 16 ml of diphenyl ether was stirred at 260° for 5 hours and, after cooling to 0°, diluted with 30 ml of tetrahydrofuran. 225 mg of sodium hydride dispersion were added and the mixture was stirred for one hour. Subsequently, 0.63 ml of (R)-methyloxirane was added and the reaction mixture was stirred at room temperature for 90 hours. The mixture was extracted with diethyl ether, water and saturated sodium chloride solution and the organic phase was dried over sodium surfate. The solvent was removed and the residue was chromatographed over 120 g of silica gel with hexane-toluene (1:1) and subsequently with toluene-ethyl acetate (19:1). 0.87 g (70%) of (R)-1-(5-fluoro-3-methylindol-1-yl)-propan-2-ol was obtained as a pale brown oil. |
Here is a chemical reaction formula: Reactants are m4:O, amount is: 0.0 MOLE;m1_m5:[H-].[Na+], amount is: 0.0 ;m2:ClC1=C(C=C2C(=CNC2=C1)C)F, amount is: 0.0 ;m3:C[C@H]1OC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:CCOCC, amount is: 0.0 MOLE;m1_m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C=C2C(=CN(C2=C1)C[C@@H](C)O)C)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 0.07 g of sodium hydride dispersion in 10 ml of tetrahydrofuran was treated with 0.33 g of 6-chloro-5-fluoro-3-methylindole at 0° and stirred as this temperature for 1 hour. After the addition of 0.19 ml of (R)-methyloxirane the reaction mixture was stirred at room temperature for 17 hours and subsequently treated with water. The mixture was diluted with ether, washed with water and with saturated sodium chloride solution and the organic phase was dried over sodium sulfate. After removal of the solvent the residue was chromatographed over 20 g of silica gel with toluene-ethyl acetate (9:1). 0.22 g (50%) of (R)-1-(6-chloro-5-fluoro-3-methylindol-1-yl)-propan-2-ol was obtained as a yellow oil. |
Here is a chemical reaction formula: Reactants are m2:[H-].[Na+], amount is: 0.0 ;m1_m4:FC=1C(=C2C(=C(NC2=CC1)C(=O)O)OC)C, amount is: 0.0 ;m3:C[C@H]1OC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:C1(=CC=CC=C1)OC1=CC=CC=C1, amount is: 0.0 ;m5:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C(=C2C(=CN(C2=CC1)C[C@@H](C)O)OC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 1.98 g of 5-fluoro-3-methoxy-4-methylindole-2-carboxylic acid in 16 ml of diphenyl ether was stirred at 260° for 0.5 hour and, after cooling to 0°, diluted with 44 ml of tetrahydrofuran. 0.33 g of sodium hydride dispersion was added and the mixture was stirred for one hour. Subsequently, 1 ml of (R)-methyloxirane was added and the reaction mixture was stirred at room temperature for 90 hours. The mixture was extracted with diethyl ether, water and saturated sodium chloride solution and the organic phase was dried over sodium surfate. The solvent was removed and the residue was chromatographed over 120 g of silica gel with toluene and toluene-ethyl acetate (9:1). 1.69 g (80%) of (R)-1-(5-fluoro-3-methoxy-4-methylindol-1-yl)-propan-2-ol were obtained as a pale brown oil. |
Here is a chemical reaction formula: Reactants are m3_m7:[N+](=O)([O-])C1=CC=C(C(=O)Cl)C=C1, amount is: 0.0 ;m4:CO, amount is: 0.0 ;m1_m2_m5_m6:OC=1C=C(C=CC1N)C1=CC(=C(C=C1)N)O, amount is: 0.0 ;m1_m2_m5_m6:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m7:O1CCCC1, amount is: 0.0 ;m1_m2_m5_m6:O1CCCC1, amount is: 0.0 ;m1_m2_m5_m6:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC1=CC=C(C(=O)NC2=C(C=C(C=C2)C2=CC(=C(C=C2)NC(C2=CC=C(C=C2)N)=O)O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 35.0 g (0.162 moles) of 3,3'-dihydroxy-4,4'-diaminobiphenyl and 36.0 g (0.356 moles) of triethylamine were dissolved in a mixed solvent of 300 ml of tetrahydrofuran and 300 ml of N,N-dimethylformamide (DMF) and cooled down to 0° C. Thereafter, a solution of 63.1 g (0.340 moles) of p-nitrobenzoyl chloride in 150 ml of tetrahydrofuran was dropped in the solution in such a way that the resultant reaction solution had a temperature not higher than 10° C. Subsequently, the reaction solution was poured into one liter of methanol thereby permitting the resulting reaction product to be precipitated, followed by filtering, washing with tetrahydrofuran, then with water and finally with methanol, and drying to obtain crude red crystals of 4,4'-bis(4-aminobenzamido)-3,3'-dihydroxybiphenyl. The yield was 82.1 g (at a yield of 99.7%). The crude crystals were recrystallized from a mixed solvent of dimethylformamide and methanol to obtain a pure product. |
Here is a chemical reaction formula: Reactants are m0_m5:COC1=C(C(=O)C2=C(C=CC=C2)O)C=CC(=C1OC)OC, amount is: 0.0 MOLE;m3:COC1=C(C(=O)O)C=CC=C1, amount is: 0.0 ;m2:COC1=C(C(=O)C2=C(C=CC=C2)O)C=CC(=C1)OC, amount is: 0.0 MOLE;m1:OC1=C(C(=O)C2=C(C=CC=C2)OC)C=CC(=C1)OC, amount is: 0.0 MOLE;m4:COC1=CC(=CC(=C1)OC)OC, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:COC=1C(=C(C(=O)C2=C(C=CC=C2)OC)C=CC1OC)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: According to the method of producing 2-hydroxy-4-methoxy-2'-methoxy benzophenone (4a) and 2,4-dimethoxy-2'-hydroxybenzophenone (4b), 2.00g (13.14 mmol) of 2-methoxybenzoic acid was reacted with 2.19g (13.04 mmol) of 1,3,5-trimethoxybenzene to give 2.20g (7.75 mmol) of 3,4-dimethoxy-2-hydroxy-2'-methoxybenzophenone (17a) and 2,3,4-trimethoxy-2'-hydroxy-benzophenone (17b). Then, based on example 3, 1.35 g (5.92 mmol) of 3,4-dihydroxy benzophenone (18H) as pale yellow powder was produced. The physical properties were measured and are listed below. |
Here is a chemical reaction formula: Reactants are m2_m4:Cl.NCC(CC(=O)O)S, amount is: 0.0 ;m1_m3:ClC1=C(C=CC(=C1Cl)Cl)C(C)S(=O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m4:O, amount is: 0.0 ;m1_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C=CC(=C1Cl)Cl)C(C)S(=O)(=O)O.NC[C@@H](CC(=O)O)S, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (-)-1-(2,3,4-Trichlorophenyl)ethanesulfonic acid (3.18 g) is dissolved in water (17.4 ml), and thereto is added aqueous solution of racemic 4-amino-3-mercaptobutyric acid hydrochloride (3.77 g) in water (24.6 ml). The mixture is dissolved at 70° C.-80° C., and allowed to cool. After cooling, the mixture is stirred under ice-cooling for one hour, and the precipitated crystals are collected by filtration, washed, and dried to give (3R)-4-amino-3-mercaptobutyric acid (-)-1-(2,3,4-trichlorophenyl)ethanesulfonate (3.81 g). |
Here is a chemical reaction formula: Reactants are m1_m2:C(C)(=O)N1C(C[C@H](C1)C(C)=O)=S, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:Cl.CO, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)(=O)[C@@H]1CC(NC1)=S, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (+)-(4R)-1-Acetyl-4-acetylthio-2-pyrrolidone (6 g) is dissolved in 5% hydrogen chloride-methanol solution, and the mixture is stirred at room temperature for 25 minutes. The mixture is evaporated to remove the solvent, and the residue is subjected to azeotropic distillation with toluene. To the residue is added acetyl chloride (6 ml), and the mixture is stirred for 4.5 hours. The precipitated crystals are collected by filtration, and dissolved in chloroform. The chloroform solution is washed with water, dried, and evaporated to remove the solvent to give (4R)-4-acetylthio-2-pyrrolidone (3.8 g). |
Here is a chemical reaction formula: Reactants are m2:[BH4-].[Na+], amount is: 0.0 ;m1:ClC1=C(C=CC(=C1Cl)Cl)C(C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC1=C(C=CC(=C1Cl)Cl)C(C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: In methanol (284 ml) is suspended 2',3',4'-trichloroacetophenone (94.7 g), and thereto is added sodium borohydride (7.6 g) at 15° C.-25° C. The mixture is stirred at 25° C. for two hours, and evaporated to remove the methanol. To the residue is added 2N hydrochloric acid (110 ml), and the mixture is extracted with ethyl acetate. The organic layer is washed with water, dried, and evaporated to remove the solvent to give crude 1-(2,3,4-trichlorophenyl)ethanol (95 g). |
Here is a chemical reaction formula: Reactants are m3:S1C(=CC=C1)CC(=O)O, amount is: 0.0 ;m1_m2_m4:C(C)(=O)N1C(C[C@H](C1)C(C)=O)=S, amount is: 0.0 ;m1_m2_m4:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)N1C(CC(C1)C(C)=O)=S, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (+)-(4R)-1-Acetyl-4-acetylthio-2-pyrrolidone (3 g) and triethylamine (2.1 ml) are dissolved in ethyl acetate (30 ml), and the mixture is refluxed for three hours, and then allowed to stand at room temperature for 8 hours. To the reaction solution is added thiolacetic acid (1.2 ml), and the mixture is stirred at room temperature for 5 hours. The reaction solution is washed with water, dried, and evaporated to remove the solvent to give (±)-1-acetyl-4-acetylthio-2-pyrrolidone (2.7 g). |
Here is a chemical reaction formula: Reactants are m1_m5:C(C)(=O)[C@@H]1CC(NC1)=S, amount is: 0.0 ;m2:P12(=S)SP3(=S)SP(=S)(S1)SP(=S)(S2)S3, amount is: 0.0 ;m3_m4:O, amount is: 0.0 MOLE;m3_m4:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5:C1(=CC=CC=C1)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)S[C@@H]1CC(NC1)=S, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (4R)-4-Acetylthio-2-pyrrolidone (10 g) is dissolved in toluene (100 ml), and thereto is added gradually phosphorus pentasulfide (9.5 g), and the mixture is stirred at room temperature for 20 minutes. To the reaction solution are added water and ethyl acetate, and the mixture is stirred at room temperature for 1.5 hour. The insoluble materials are removed by filtration, and the organic layer is washed with water, dried, and evaporated to remove the solvent. The residue is recrystallized from toluene to give (+)-(4R)-4-acetylthiopyrrolidine-2-thione (7.9 g). |
Here is a chemical reaction formula: Reactants are m1_m3_m2_m4:N1CCC(C2=CC=CC=C12)CCN1CCC(CC1)C1=CC(=C(C=C1)OC)OC, amount is: 0.0 ;m1_m3_m2_m4:C(C)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2_m4:C1CCOC1, amount is: 0.0 ;m1_m3_m2_m4:C1CCOC1, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)(=O)N1CCC(C2=CC=CC=C12)CCN1CCC(CC1)C1=CC(=C(C=C1)OC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2.5 g of 1-(2-(1,2,3,4-tetrahydroquinolin-4-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine (dihydrochloride, m.p 235°-236°) in 35 ml of THF is treated with a solution of 0.9 g of a acetyl chloride in ml of THF, stirred for 2 hours at-50°, evaporated and worked up in the customary manner. 1-(2-(1,2,3,4-Tetrahydro-1-acetylquinolin-4-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine is obtained. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C1(CCCC2=CC=CC=C12)CCN1CCC(CC1)C1=CC(=C(C=C1)OC)OC, amount is: 0.0 ;m1_m2_m3:Cl.N1=CC=CC=C1, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m3:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CCCC2=CC=CC=C12)CCN1CCC(CC1)C1=CC(=C(C=C1)O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4.1 g of 1-(2-(tetralin-1-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine (fumarate, m.p. 154°-156°) 3.2 g of pyridine hydrochloride and 80 ml of pyridine is boiled for 3 hours. It is cooled, evaporated and worked up in the customary manner and gives 1-(2-(tetralin-1-yl)ethyl)-4-(3,4-dihydroxyphenyl)piperidine. |
Here is a chemical reaction formula: Reactants are m1_m2:Cl.COC=1C=C(C=CC1OC)C1CCNCC1, amount is: 0.0 MOLE;m1_m2:[N+](=O)([O-])C=1C=C2CCCC(C2=CC1)CCBr, amount is: 0.0 MOLE,this reaction does not need reagents,this reaction does not need solvents,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C=1C=C2CCCC(C2=CC1)CCN1CCC(CC1)C1=CC(=C(C=C1)OC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Analogously to Example 5, reaction of 4-(3,4-dimethoxyphenyl)piperidine hydrochloride with 2-(6-nitrotetralin-1-yl)ethyl bromide gives 1-(2-(6-nitrotetralin-1-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine. |
Here is a chemical reaction formula: Reactants are m1_m2:[N+](=O)([O-])C=1C=C2CCCC(C2=CC1)CCN1CCC(CC1)C1=CC(=C(C=C1)OC)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:NC=1C=C2CCCC(C2=CC1)CCN1CCC(CC1)C1=CC(=C(C=C1)OC)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 3.2 g of 1-(2-(6-nitrotetralin-1-yl)ethyl)-4-(3,4-dimethoxyphenyl)piperidine in 50 ml of methanol is hydrogenated in the presence of 1.6 g of Pd/C (5%) until the absorption of hydrogen has come to a standstill. The catalyst is filtered off, and the filtrate is worked up in the customary manner and gives 1-(2-(6-aminotetralin-1-yl) ethyl)-4-(3,4-dimethoxyphenyl)piperidine. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:C(C1=CC=CC=C1)[C@@H]1NC(O[C@@H]1COS(=O)(=O)C1=CC=C(C=C1)[N+](=O)[O-])=O, amount is: 0.0 ;m1_m2_m3_m4:C(C)(C)(C)NC(=O)[C@H]1NC[C@H]2CCCC[C@H]2C1, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m5_m6:CC(CC(C)=O)C, amount is: 0.0 ;m5_m6:Cl, amount is: 0.0 ;m1_m2_m3_m4:CC(CC(C)=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)O.C(C1=CC=CC=C1)[C@@H]1NC(O[C@@H]1CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A suspension of 24.69 g of p-nitrobenzenesulphonic acid (4S, 5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester (Example 12), 15.0 g of N-tert.butyl-decahydro-(4aS,8aS)-isoquinoline-3(S)-carboxamide and 10.0 g of sodium carbonate in 76 ml of 4-methyl-2-pentanone is heated under reflux for 10 hours while stirring. The suspension is cooled to 80° C., diluted with 176 ml of 4-methyl-2-pentanone and 54 ml of 3N hydrochloric acid, cooled to 40° C. and filtered. The residue is washed with water and 4-methyl-2-pentanone and dried to give 35.1 g (88%) of (3S,4aS,8aS)-2-[(4S,5R)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl]-N-tert.butyl-decahydro-isoquinoline-3-carboxamide p-nitrobenzenesulphonate, [α]D20 =-31.2° (1% in DMF). |
Here is a chemical reaction formula: Reactants are m3:O, amount is: 0.0 ;m1:C(C1=CC=CC=C1)C1NC(OC1C(=O)OC)=O, amount is: 0.0 MOLE;m4:Cl, amount is: 0.0 ;m2_m5:[BH4-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)[C@@H]1NC(O[C@@H]1CO)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 150 g of the 98:2 mixture of (4S,5S) and (4S,5R) isomers of methyl 4-benzyl-2-oxo-oxazolidine-5-carboxylate from Example 7B) are added at 15°-20° C. over 1.5 hours to a stirred solution of 20.8 g of NaBH4 in 360 ml of ethanol and stirred for 2 hours. The suspension is treated with 540 ml of water at 20° C. and the pH is brought to 7 with 165 ml of 3N hydrochloric acid. The suspension is stirred at 22° C. for 2.5 hours, left to stand at 4° C. for 18 hours, then filtered and the residue is washed with water and dried to give 111.6 g (84%) of 99% (4S,5S)-4-benzyl-5-hydroxymethyl-oxazolidin-2-one, m.p. 167.3°-168.9° C., [α]D20 : -79.4° (1% in methanol). |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m6_m7:CS(=O)(=O)Cl, amount is: 0.0 ;m1_m5_m2_m6_m7:C(C1=CC=CC=C1)[C@@H]1NC(O[C@@H]1CO)=O, amount is: 0.0 ;m3_m4:C(=O)(O)[O-].[Na+], amount is: 0.0 ;m3_m4:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m8:CN1CCOCC1, amount is: 0.0 ;m1_m5_m2_m6_m7:CC(=O)C, amount is: 0.0 ;m1_m5_m2_m6_m7:CC(=O)C, amount is: 0.0 ;m1_m5_m2_m6_m7:CN1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)[C@@H]1NC(O[C@@H]1COS(=O)(=O)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4.7 ml of methanesulphonyl chloride in 10 ml of acetone is added at 25° C. to a suspension of 10.4 g of the alcohol from Example 8 in 20 ml of acetone and 6.1 ml of N-methylmorpholine and the suspension is stirred at 25° C. for 3 hours. A further 1.1 ml of N-methylmorpholine are added and the mixture is stirred for 1 hour. The suspension is shaken with 80 ml of semi-saturated NaHCO3 solution and ethyl acetate and the separated aqueous phase is extracted with ethyl acetate. The ethyl acetate extracts are washed with water, dried and filtered. The filtrate is concentrated to give 14.3 g (100%) of crude methanesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester, TLC (SiO2 ethyl acetate): Rf =0.4; MS (El): 286 (M+H+). |
Here is a chemical reaction formula: Reactants are m1_m2_m5_m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m5_m3:C(C1=CC=CC=C1)[C@@H]1NC(O[C@@H]1CO)=O, amount is: 0.0 ;m1_m2_m5_m3:C1(=CC=C(C=C1)S(=O)(=O)Cl)C, amount is: 0.0 ;m4:O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m5_m3:CC(=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)[C@@H]1NC(O[C@@H]1COS(=O)(=O)C1=CC=C(C=C1)C)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 5.6 ml of triethylamine are added at 22° C. to a stirred suspension of 5.55 g of the alcohol from Example 8 in 27 ml of acetone and 6.64 g of p-toluenesulphonyl chloride and stirred at 22° C. for 6.5 hours. The suspension is treated with water, stirred at 10° C., filtered, the residue is washed with a water/acetone solution (3:2) and dried to give 9.09 g (94.%) of 99% p-toluenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester, m.p. 148.7°-150.3° C., [α]D20 : +3.0° (1% acetone). |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m5:[N+](=O)([O-])C1=CC=C(C=C1)S(=O)(=O)Cl, amount is: 0.0 ;m1_m2_m4_m5:C(C1=CC=CC=C1)[C@@H]1NC(O[C@@H]1CO)=O, amount is: 0.0 ;m3:C([O-])(O)=O.[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m4_m5:C1CCOC1, amount is: 0.0 ;m1_m2_m4_m5:CN1CCOCC1, amount is: 0.0 ;m6:CN1CCOCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)[C@@H]1NC(O[C@@H]1COS(=O)(=O)C1=CC=C(C=C1)[N+](=O)[O-])=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 15.4 g of p-nitrobenzenesulphonyl chloride are added in portions at 20°-25° C. to a stirred suspension of 12.0 g of the alcohol from Example 8 in 35 ml of THF and 7.66 ml of N-methylmorpholine and stirred for 4.5 hours. The suspension is again treated with 0.77 ml of N-methylmorpholine and stirred at 22° C. for 4.5 hours. The mixture is treated with 70 ml of a 2% sodium bicarbonate solution, stirred for 1.5 hours, filtered, the residue is washed with water and ethanol and dried to give 21.4 g (94%) of 98.5 % p-nitrobenzenesulphonic acid (4S,5S)-4-benzyl-2-oxo-oxazolidin-5-ylmethyl ester, m.p. 148°-149.5° C., [α]D20 : +10.0° (1% in acetone). |
Here is a chemical reaction formula: Reactants are m1_m2_m4:C(C)/C(/C=C/CO)=C\C, amount is: 0.0 ;m1_m2_m4:C(C)N(CC)CC, amount is: 0.0 ;m3:Cl.C(C1=CN=CC=C1)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1=CC(=CC=C1)C(=O)OCC=CC(=CC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of (E,E)-4-ethyl-2,4-hexadien-1-ol (2.0 g), triethylamine (8 ml), and dichloromethane (15 ml) at 0° C. was added nicotinic acid chloride hydrochloride (4.23 g). The solution was stirred at 0° C. for 1.5 hours and at room temperature for 14 hours. The reaction mixture was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (chloroform) to give 4-ethyl-2,4-hexadien-1-yl 3-pyridinecarboxylate (3.3 g) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:C(C)/C(/C=C/CO)=C\C, amount is: 0.0 ;m1_m2_m4:[O-]C#N.[Na+], amount is: 0.0 ;m3:FC(C(=O)O)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:C1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(N)(OCC=CC(=CC)CC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of (E,E)-4-ethyl-2,4-hexadien-1-ol (3.0 g), sodium cyanate (3.1 g), and benzene (15 ml) at room temperature was added dropwise trifluoroacetic acid (5.42 g) during 1 hour. After being stirred for 2 hours at the same temperature, the reaction mixture was partitioned between water and ethyl acetate. The organic layer separated was washed with aqueous sodium bicarbonate, water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (1% methanol-dichloromethane) to give 2.0 g of 4-ethyl-2,4-hexadien-1-yl carbamate. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)/C(/C=C/CO)=C\C, amount is: 0.0 ;m1_m2_m3:C(C)N=C=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:ClCCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)NC(OC\C=C\C(=C\C)\CC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of (E,E)-4-ethyl-2,4-hexadien-1-ol (2.0 g) and ethyl isocyanate (1.13 g) in 1,2-dichloroethane (12 ml) was stirred at 0° C. for 3 hours and at room temperature for 12 hours. The reaction mixture was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (chloroform) to give (E,E)-4-ethyl-2,4-hexadien-1-yl ethylcarbamate (2.5 g) as an oil. |
Here is a chemical reaction formula: Reactants are m4_m5:N(=NC(=O)OCC)C(=O)OCC, amount is: 0.0 ;m1_m2_m3_m7:C(C)/C(/C=C/CO)=C\C, amount is: 0.0 ;m1_m2_m3_m7:C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3_m7:C1(C=2C(C(N1)=O)=CC=CC2)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m5:O1CCCC1, amount is: 0.0 ;m1_m2_m3_m7:O1CCCC1, amount is: 0.0 ;m6:ClCCl, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)C(C=CCN1C(C=2C(C1=O)=CC=CC2)=O)=CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of (E,E)-4-ethyl-2,4-hexadien-1-ol (1.0 g), triphenylphosphine (2.29 g), phthalimide (1.17 g), and tetrahydrofuran (30 ml) at room temperature was added a solution of diethyl azodicarboxylate (1.52 g) in tetrahydrofuran (5 ml). The mixture was stirred at room temperature for 2 days. The reaction mixture was diluted with dichloromethane, washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (hexane-dichloromethane, 2:3) to give 0.42 g of N-(4-ethyl-2,4-hexadien-1-yl)phthalimide as crystals. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)C(C=CCN1C(C=2C(C1=O)=CC=CC2)=O)=CC, amount is: 0.0 ;m1_m2_m3:O.NN, amount is: 0.0 ;m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)C(C=CCN)=CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-(4-ethyl-2,4-hexadien-1-yl)phthalimide (500 mg), hydrazine monohydrate (147 mg), and ethanol (5 ml) was refluxed for 40 minutes under nitrogen atmosphere. After cooling, the precipitate was filtered and washed with ethanol. Evaporation of the filtrate gave a crystalline residue which was dissolved in 1N sodium hydroxide solution and extracted with dichloromethane. The organic extract was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated to give 4-ethyl-2,4-hexadien-1-ylamine (205 mg) as an oil. This oil was used in the next reaction without further purification. To a solution of crude 4-ethyl-2,4-hexadien-1-ylamine (205 mg) in dichloromethane (2 ml) at 0° C. was added dropwise acetic anhydride (335 mg). After one hour, the reaction mixture was evaporated to dryness. The residue was chromatographed on silica gel (2% methanol in dichloromethane) to give 1-acetylamino-4-ethyl-2,4-hexadiene (122 mg) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C)C(C=CCN)=CC, amount is: 0.0 ;m1_m3_m2:C(C)(=O)OC(C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)NCC=CC(=CC)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-(4-ethyl-2,4-hexadien-1-yl)phthalimide (500 mg), hydrazine monohydrate (147 mg), and ethanol (5 ml) was refluxed for 40 minutes under nitrogen atmosphere. After cooling, the precipitate was filtered and washed with ethanol. Evaporation of the filtrate gave a crystalline residue which was dissolved in 1N sodium hydroxide solution and extracted with dichloromethane. The organic extract was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated to give 4-ethyl-2,4-hexadien-1-ylamine (205 mg) as an oil. This oil was used in the next reaction without further purification. To a solution of crude 4-ethyl-2,4-hexadien-1-ylamine (205 mg) in dichloromethane (2 ml) at 0° C. was added dropwise acetic anhydride (335 mg). After one hour, the reaction mixture was evaporated to dryness. The residue was chromatographed on silica gel (2% methanol in dichloromethane) to give 1-acetylamino-4-ethyl-2,4-hexadiene (122 mg) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)C(C=CCN1C(C=2C(C1=O)=CC=CC2)=O)=CC, amount is: 0.0 ;m1_m2_m3:O.NN, amount is: 0.0 ;m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)C(C=CCN)=CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-(4-ethyl-2,4-hexadien-1-yl)phthalimide (5.0 g), hydrazine monohydrate (2.45 g), and ethanol (150 ml) was refluxed for 1.5 hours under nitrogen atmosphere. After cooling, the precipitate was filtered and washed with ethanol. Evaporation of the filtrate gave a crystalline residue which was dissolved in 1N sodium hydroxide solution and extracted with dichloromethane. The organic extract was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated to give crude 4-ethyl-2,4-hexadien-1-ylamine (2.59 g) as an oil. The crude oil was dissolved in dichloromethane (30 ml) containing triethylamine (6.28 g). To this solution cooled to 0° C. was added nicotinic acid chloride hydrochloride (3.41 g) in small portions during 10 minutes. After 30 minutes, triethylamine (4.19 g) and nicotinic acid chloride hydrochloride (0.79 g) were added and the mixture was stirred for 30 minutes at 0° C. The reaction mixture was diluted with dichloromethane, washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (2% methanol-dichloromethane) to give a mixture of N-[(2E,4E) and (2Z,4E)-4-ethyl-2,4-hexadien-1-yl]-3-pyridinecarboxamide (4.6 g) which crystallized on standing. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)C(C=CCN1C(C=2C(C1=O)=CC=CC2)=O)=CC, amount is: 0.0 ;m1_m2_m3:O.NN, amount is: 0.0 ;m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(C)C(C=CCN)=CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-(4-ethyl-2,4-hexadien-1-yl)phthalimide (3.0 g), hydrazine monohydrate (0.88 g), and ethanol (30 ml) was refluxed for 40 minutes under nitrogen atmosphere. After cooling, the precipitate was filtered and washed with ethanol. Evaporation of the filtrate gave a crystalline residue which was dissolved in 1N sodium hydroxide solution and extracted with dichloromethane. The organic extract was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated to give 4-ethyl-2,4-hexadien-1-ylamine as an oil. To a mixture of crude 4-ethyl-2,4-hexadien-1-ylamine, triethylamine (1.79 g), and dichloromethane (30 ml) at 0° C. was added dropwise dimethylsulfamoyl chloride (2.03 g) during 10 minutes. After 30 minutes, triethylamine (0.6 g) and dimethylsulfamoyl chloride (0.85 g) were added to the reaction mixture. After 1 hour at 0° C., the reaction mixture was washed with water and aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (dichloromethane-hexane, 7:3) to give N,N-dimethyl-N'-(4-ethyl-2,4-hexadien-1-yl)sulfamide (924 mg) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m6_m2:C(C)C(C=CCN)=CC, amount is: 0.0 MOLE;m1_m6_m2:ClCCl, amount is: 0.0 ;m5_m4:CN(S(=O)(=O)Cl)C, amount is: 0.0 ;m3:CN(S(=O)(=O)Cl)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m6_m2:C(C)N(CC)CC, amount is: 0.0 ;m5_m4:C(C)N(CC)CC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:CN(S(=O)(=O)NCC=CC(=CC)CC)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-(4-ethyl-2,4-hexadien-1-yl)phthalimide (3.0 g), hydrazine monohydrate (0.88 g), and ethanol (30 ml) was refluxed for 40 minutes under nitrogen atmosphere. After cooling, the precipitate was filtered and washed with ethanol. Evaporation of the filtrate gave a crystalline residue which was dissolved in 1N sodium hydroxide solution and extracted with dichloromethane. The organic extract was washed with water and brine, dried over anhydrous sodium sulfate, and evaporated to give 4-ethyl-2,4-hexadien-1-ylamine as an oil. To a mixture of crude 4-ethyl-2,4-hexadien-1-ylamine, triethylamine (1.79 g), and dichloromethane (30 ml) at 0° C. was added dropwise dimethylsulfamoyl chloride (2.03 g) during 10 minutes. After 30 minutes, triethylamine (0.6 g) and dimethylsulfamoyl chloride (0.85 g) were added to the reaction mixture. After 1 hour at 0° C., the reaction mixture was washed with water and aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (dichloromethane-hexane, 7:3) to give N,N-dimethyl-N'-(4-ethyl-2,4-hexadien-1-yl)sulfamide (924 mg) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3_m5:C(C)C(C=CCN)=CC, amount is: 0.0 ;m1_m2_m4_m3_m5:C(#N)N=C(OC(C)C)C=1C=NC=CC1, amount is: 0.0 ;m1_m2_m4_m3_m5:C[O-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m2_m4_m3_m5:CO, amount is: 0.0 ;m1_m2_m4_m3_m5:CO, amount is: 0.0 ;m6:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:C(#N)NC(=NCC=CC(=CC)CC)C=1C=NC=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of crude 4-ethyl-2,4-hexadien-1-ylamine (1.38 g) and isopropyl N-cyano-3-pyridinecarboximidate (1.74 g) in methanol (35 ml) at room temperature was added 28% sodium methoxide in methanol (2.13 g). After 10 minutes, the mixture was diluted with water and extracted three times with dichloromethane. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (5% methanol in dichloromethane) to give N-cyano-N'-(4-ethyl-2,4-hexadien-1-yl)-3-pyridinecarboximidamide (1.89 g) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C)/C(/C=C/CO)=C\C(C)C, amount is: 0.0 ;m1_m3_m2:C(C)(=O)OC(C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4:ClCCl, amount is: 0.0 MOLE;m1_m3_m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)OC\C=C\C(=C\C(C)C)\CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of (E,E)-4-ethyl-6-methyl-2,4-heptadien-1-ol (23.8 g) in pyridine (61.4 g) at 0° C. was added dropwise acetic anhydride (50.9 g). After two hours, the reaction mixture was diluted with dichloromethane. The solution was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (3% ethyl acetate-hexane) to give (E,E)-1-acetoxy-4-ethyl-6-methyl-2,4-heptadiene (24.11 g) as an oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C)C(C=CCN1C(C=2C(C1=O)=CC=CC2)=O)=CC(C)C, amount is: 0.0 ;m1_m2_m3:O.NN, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)C(C=CCN)=CC(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of N-(4-ethyl-6-methyl-2,4-heptadiene-1-yl)phthalimide (17.62 g), hydrazine monohydrate (9.9 g), and ethanol (700 ml) was refluxed for 90 minutes under nitrogen atmosphere. The reaction mixture was evaporated in vacuo. The residue was dissolved in 10% aqueous potassium carbonate solution and extracted with ethyl acetate. The organic extract was washed with brine, dried over anhydrous magnesium sulfate, and evaporated to give 4-ethyl-6-methyl-2,4-heptadiene-1-ylamine as an oil. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m4_m3:C(C)C(C=CCN)=CC(C)C, amount is: 0.0 ;m1_m2_m4_m3:Cl.C(C1=CN=CC=C1)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)C(C=CCNC(=O)C=1C=NC=CC1)=CC(C)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of triethylamine (5.06 g) and 4-ethyl-6-methyl-2,4-heptadiene-1-ylamine (3.06 g) in dichloromethane (50 ml) at 0° C. was added nicotinic acid chloride hydrochloride (3.56 g) in small portions during 5 minutes. The mixture was stirred for 30 minutes at 0° C. The reaction mixture was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was dissolved in isopropyl ether (20 ml) and allowed to stand at 5° C. overnight to give 4.46 g of N-(4-ethyl-6-methyl-2,4-heptadiene-1-yl)-3-pyridinecarboxamide. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:C(C)N(CC)CC, amount is: 0.0 ;m1_m2_m4_m3:C(C)C(C=CCN)=CC(C)C, amount is: 0.0 ;m1_m2_m4_m3:C(C)(=O)OC(C)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:ClCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)(=O)NCC=CC(=CC(C)C)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of triethylamine (2.22 g) and 4-ethyl-6-methyl-2,4-heptadiene-1-ylamine (3.07 g) in dichloromethane (50 ml) at 0° C. was added dropwise acetic anhydride (4.08 g). After one hour, the reaction mixture was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (10% methanol-chloroform) to give 1-acetylamino-4-ethyl-6-methyl-2,4-heptadiene (3.86 g) as an oil. |