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Here is a chemical reaction formula: Reactants are m2:CS(=O)(=O)OCC1=C(C=CC=C1)OC, amount is: 0.0 MOLE;m1:N1C=CC=2C(=CC=CC12)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:COC1=C(CN2C=CC=3C(=CC=CC23)C=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 725 mg of indole-4-carbaldehyde and 2-methoxybenzyl methanesulfonate instead of the benzyl bromide used in Example 1 to give 906 mg of 1-(2-methoxybenzyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 68%. |
Here is a chemical reaction formula: Reactants are m2:CS(=O)(=O)OCC1=CC(=CC(=C1)OC)OC, amount is: 0.0 MOLE;m1:N1C=CC=2C(=CC=CC12)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:COC=1C=C(CN2C=CC=3C(=CC=CC23)C=O)C=C(C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 725 mg of indole-4-carbaldehyde and 3,5-dimethoxybenzyl methanesulfonate instead of the benzyl bromide used in Example 1 to give 1.29 g of 1-(3,5-dimethoxybenzyl)indole-4-carbaldehyde as a pale brown amorphous substance. The yield thereof was found to be 86%. |
Here is a chemical reaction formula: Reactants are m2:CS(=O)(=O)OCC1=C(C=CC(=C1)OC)OC, amount is: 0.0 MOLE;m1:N1C=CC=2C(=CC=CC12)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:COC1=C(CN2C=CC=3C(=CC=CC23)C=O)C=C(C=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 725 mg of indole-4-carbaldehyde and 2,5-dimethoxybenzyl methanesulfonate instead of the benzyl bromide used in Example 1 to give 940 mg of 1-(2,5-dimethoxybenzyl)indole-4-carbaldehyde as pale yellow crystals. The yield thereof was found to be 64%. |
Here is a chemical reaction formula: Reactants are m2:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1:ClC1=CC=C(CBr)C=C1, 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:ClC1=CC=C(CN2C=CC=3C(=CC=CC23)C=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 2.97 g of 4-chlorobenzyl bromide and 2.00 g of indole-4-carbaldehyde as a starting material to give 3.70 g of 1-(4-chlorobenzyl)indole-4-carbaldehyde as yellow crystals. The yield thereof was found to be 100%. |
Here is a chemical reaction formula: Reactants are m1:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m2:CS(=O)(=O)OCC=1SC=CC1, 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:S1C(=CC=C1)CN1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 725 mg of indole-4-carbaldehyde and 2-thienylmethyl methanesulfonate instead of the benzyl bromide used in Example 1 to give 392 mg of 1-(2-thienylmethyl)indole-4-carbaldehyde as pale yellow crystals. The yield thereof was found to be 33%. |
Here is a chemical reaction formula: Reactants are m2:CS(=O)(=O)OCCC=1SC=CC1, amount is: 0.0 ;m1:N1C=CC=2C(=CC=CC12)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:S1C(=CC=C1)CCN1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 435 mg of indole-4-carbaldehyde and 680 mg of 2-(thien-2-yl)ethyl methanesulfonate instead of the benzyl bromide used in Example 1 to give 299 mg of 1-[2-(thien-2-yl)ethyl]indole-4-carbaldehyde as an orange-colored oily substance. The yield thereof was found to be 39%. |
Here is a chemical reaction formula: Reactants are m2:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1:BrCC(CC)CC, 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)C(CN1C=CC=2C(=CC=CC12)C=O)CC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 4.55 g of 1-bromo-2-ethylbutane and 2.00 g of indole-4-carbaldehyde as a starting material to give 1.92 g of 1-(2-ethylbutyl) indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 61%. |
Here is a chemical reaction formula: Reactants are m2:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1:C1(CCCCC1)CBr, 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:C1(CCCCC1)CN1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 4.93 g of cyclohexylmethyl bromide and 2.00 g of indole-4-carbaldehyde as a starting material to give 2.82 g of 1-cyclohexylmethylindole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 85%. |
Here is a chemical reaction formula: Reactants are m1:BrCCC=C(C)C, amount is: 0.0 ;m2:N1C=CC=2C(=CC=CC12)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:CC(=CCCN1C=CC=2C(=CC=CC12)C=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 7 were repeated except for using 4.59 g of 5-bromo-2-methyl-2-pentene and 2.00 g of indole-4-carbaldehyde as a starting material to give 2.72 g of 1-(4-methyl-3-pentenyl)indole-4-carbaldehyde as a brown oily substance. The yield thereof was found to be 87%. |
Here is a chemical reaction formula: Reactants are m2:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1:CS(=O)(=O)OCCN1CCCC1, 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:N1(CCCC1)CCN1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 154 were repeated except for using 5.32 g of N-(2-methanesulfonyloxyethyl)pyrrolidine and 2.00 g of indole-4-carbaldehyde as a starting material to give 1.08 g of 1-[2-(pyrrolidin-1-yl)ethyl]indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 33%. |
Here is a chemical reaction formula: Reactants are m2:C1(=CC=CC=C1)C(C)Br, amount is: 0.0 ;m1:N1C=CC=2C(=CC=CC12)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:CC(C1=CC=CC=C1)N1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 4 were repeated except for using 703 mg of indole-4-carbaldehyde and 987 mg of α-phenylethyl bromide instead of the 4-picolyl chloride hydrochloride to give 845 mg of 1-(α-methylbenzyl)indole-4-carbaldehyde as an orange-colored oily substance. The yield thereof was found to be 70%. |
Here is a chemical reaction formula: Reactants are m2:C(C1=CC=CC=C1)(C1=CC=CC=C1)Cl, amount is: 0.0 MOLE;m1:N1C=CC=2C(=CC=CC12)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(C1=CC=CC=C1)(C1=CC=CC=C1)N1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 870 mg of indole-4-carbaldehyde and benzhydryl chloride instead of the benzyl bromide used in Example 1 to give 1.14 g of 1-benzhydrylindole-4-carbaldehyde as an orange-colored oily substance. The yield thereof was found to be 61%. |
Here is a chemical reaction formula: Reactants are m1:BrC1C=CCCC1, amount is: 0.0 ;m2:N1C=CC=2C(=CC=CC12)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:C1(C=CCCC1)N1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 2.44 g of 3-bromocyclohexene and 2.00 g of indole-4-carbaldehyde as a starting material to give 556 mg of 1-(2-cyclohexenyl)indole-4-carbaldehyde as a yellow-colored oily substance. The yield thereof was found to be 18%. |
Here is a chemical reaction formula: Reactants are m1:BrCC(=O)C1=CC=CC=C1, amount is: 0.0 ;m2:N1C=CC=2C(=CC=CC12)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)C1=CC=CC=C1)N1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 7 were repeated except for using 5.49 g of bromoacetophenone and 2.00 g of indole-4-carbaldehyde as a starting material to give 494 mg of 1-phenacylindole-4-carbaldehyde as yellow crystals. The yield thereof was found to be 14%. |
Here is a chemical reaction formula: Reactants are m2:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1:[N+](=O)([O-])C1=CC=C(CBr)C=C1, 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:[N+](=O)([O-])C1=CC=C(CN2C=CC=3C(=CC=CC23)C=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 7 were repeated except for using 4.46 g of 4-nitrobenzyl bromide and 2.00 g of indole-4-carbaldehyde as a starting material to give 2.14 g of 1-(4-nitrobenzyl) indole-4-carbaldehyde as an orange-colored oily substance. The yield thereof was found to be 59%. |
Here is a chemical reaction formula: Reactants are m1:CS(=O)(=O)OCC1=C(C=C(C=C1)OC)OC, amount is: 0.0 ;m2:N1C=CC=2C(=CC=CC12)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:COC1=C(CN2C=CC=3C(=CC=CC23)C=O)C=CC(=C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 2.03 g of 2,4-dimethoxybenzyl methanesulfonate and 2.00 g of indole-4-carbaldehyde as a starting material to give 602 mg of 1-(2,4-dimethoxybenzyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 15%. |
Here is a chemical reaction formula: Reactants are m1:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m2:CS(=O)(=O)OCC1COC2=C(O1)C=CC=C2, 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:O1C(COC2=C1C=CC=C2)CN2C=CC=1C(=CC=CC21)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 870 mg of indole-4-carbaldehyde and 2-benzodioxanylmethyl methanesulfonate instead of the benzyl bromide used in Example 1 to give 699 mg of 1-(2-benzodioxanylmethyl)indole-4-carbaldehyde as a pale yellow oily substance. The yield thereof was found to be 40%. |
Here is a chemical reaction formula: Reactants are m1:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m2:CS(=O)(=O)OC(CCC=C(C)C)C, 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:CC(C)=CCCC(C)N1C=CC=2C(=CC=CC12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 1.02 g of indole-4-carbaldehyde and (2-methyl-2-hepten-6-yl) methanesulfonate instead of the benzyl bromide used in Example 1 to give 1.36 g of 1-(2-methyl-2-hepten-6-yl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 76%. |
Here is a chemical reaction formula: Reactants are m2:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1:FC(C=1C=C(CCS(=O)(=O)[O-])C=C(C1)C(F)(F)F)(F)F, 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:FC(C=1C=C(CN2C=CC=3C(=CC=CC23)C=O)C=C(C1)C(F)(F)F)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 4.80 g of [3,5-bis(trifluoromethyl)benzyl]methanesulfonate and 2.00 g of indole-4-carbaldehyde as a starting material to give 4.24 g of 1-[3,5-bis(trifluoromethyl)benzyl]indole-4-carbaldehyde as pale yellow crystals. The yield thereof was found to be 83%. |
Here is a chemical reaction formula: Reactants are m2:ClCC=C(C)C, amount is: 0.0 MOLE;m1:N1C=CC=2C(=CC=CC12)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:CC(=CCN1C=CC=2C(=CC=CC12)C=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 725 mg of indole-4-carbaldehyde and 1-chloro-3-methyl-2-butene instead of the benzyl bromide used in Example 1 to give 554 mg of 1-(3-methyl-2-butenyl)indole-4-carbaldehyde as an orange-colored oily substance. The yield thereof was found to be 52%. |
Here is a chemical reaction formula: Reactants are m2:N1C=CC=2C(=CC=CC12)C=O, amount is: 0.0 ;m1:BrC1=C(CBr)C=CC=C1, 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:BrC1=C(CC=2NC=3C=CC=C(C3C2)C=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 3.78 g of o-bromobenzyl bromide and 2.00 g of indole-4-carbaldehyde as a starting material to give 4.18 g of (2-bromobenzyl) indole-4-carbaldehyde as pale yellow crystals. The yield thereof was found to be 97%. |
Here is a chemical reaction formula: Reactants are m2:C1(=CC=CC=C1)C(C)Br, amount is: 0.0 MOLE;m1:N1C=C(C2=CC=CC=C12)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:CC(C1=CC=CC=C1)N1C=C(C2=CC=CC=C12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 870 mg of indole-3-carbaldehyde and α-phenylethyl bromide in place of the benzyl bromide used in Example 1 to give 1.42 g of 1-(α-methylbenzyl)indole-3-carbaldehyde as an orange-colored oily substance. The yield thereof was found to be 95%. |
Here is a chemical reaction formula: Reactants are m2:FC=1C=C(CBr)C=CC1F, amount is: 0.0 MOLE;m1:N1C=C(C2=CC=CC=C12)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:FC=1C=C(CN2C=C(C3=CC=CC=C23)C=O)C=CC1F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 870 mg of indole-3-carbaldehyde and 3,4-difluorobenzyl bromide in place of the benzyl bromide used in Example 1 to give 1.59 g of 1-(3,4-difluorobenzyl)indole-3-carbaldehyde as pale brown crystals. The yield thereof was found to be 98%. |
Here is a chemical reaction formula: Reactants are m2:FC1=C(CBr)C=CC=C1, amount is: 0.0 MOLE;m1:N1C=C(C2=CC=CC=C12)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:FC1=C(CN2C=C(C3=CC=CC=C23)C=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 870 mg of indole-3-carbaldehyde and 2-fluorobenzyl bromide in place of the benzyl bromide used in Example 1 to give 1.46 g of 1-(2-fluorobenzyl)indole-3-carbaldehyde as yellowish brown crystals. The yield thereof was found to be 96%. |
Here is a chemical reaction formula: Reactants are m2:CS(=O)(=O)OCC1=C(C=CC=C1)OC, amount is: 0.0 MOLE;m1:N1C=C(C2=CC=CC=C12)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:COC1=C(CN2C=C(C3=CC=CC=C23)C=O)C=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 870 mg of indole-3-carbaldehyde and 2-methoxybenzyl methanesulfonate in place of the benzyl bromide used in Example 1 to give 926 mg of 1-(2-methoxybenzyl)indole-3-carbaldehyde as pale yellow crystals. The yield thereof was found to be 58%. |
Here is a chemical reaction formula: Reactants are m1:BrCCC=C(C)C, amount is: 0.0 ;m2:N1C=C(C2=CC=CC=C12)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:CC(=CCCN1C=C(C2=CC=CC=C12)C=O)C, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 2.52 g of 5-bromo-2-methyl-2-pentene and 2.00 g of indole-3-carbaldehyde as a starting material to give 3.06 g of 1-(4-methyl-3-pentenyl)indole-3-carbaldehyde as colorless crystals. The yield thereof was found to be 98%. |
Here is a chemical reaction formula: Reactants are m2:N1C=C(C2=CC=CC=C12)C=O, amount is: 0.0 ;m1:CS(=O)(=O)OCC1=CC(=CC=C1)C(F)(F)F, 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:FC(C=1C=C(CN2C=C(C3=CC=CC=C23)C=O)C=CC1)(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 3.68 g of (3-trifluoromethylbenzyl) methanesulfonate and 2.00 g of indole-3-carbaldehyde as a starting material to give 3.98 g of 1-(3-trifluoromethylbenzyl)indole-3-carbaldehyde as pale yellow crystals. The yield thereof was found to be 95%. |
Here is a chemical reaction formula: Reactants are m1:FC1=CC=C(CBr)C=C1, amount is: 0.0 ;m2:N1C=C(C2=CC=CC=C12)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:FC1=CC=C(CC=2NC3=CC=CC=C3C2C=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 2.74 g of 4-fluorobenzyl bromide and 2.00 g of indole-3-carbaldehyde as a starting material to give 3.18 g of (4-fluorobenzyl) indole-3-carbaldehyde as colorless crystals. The yield thereof was found to be 91%. |
Here is a chemical reaction formula: Reactants are m2:N1C=C(C2=CC=CC=C12)C=O, amount is: 0.0 ;m1:FC1=C(CBr)C=C(C=C1)F, 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:FC1=C(CN2C=C(C3=CC=CC=C23)C=O)C=C(C=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 3.06 g of 2,5-difluorobenzyl bromide and 2.00 g of indole-3-carbaldehyde as a starting material to give 3.46 g of 1-(2,5-difluorobenzyl)indole-3-carbaldehyde as pale yellow crystals. The yield thereof was found to be 93%. |
Here is a chemical reaction formula: Reactants are m2:N1C=C(C2=CC=CC=C12)C=O, amount is: 0.0 ;m1:ClC1=CC=C(CBr)C=C1, 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:ClC1=CC=C(CN2C=C(C3=CC=CC=C23)C=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 2.98 g of 4-chlorobenzyl bromide and 2.00 g of indole-3-carbaldehyde as a starting material to give 3.42 g of 1-(4-chlorobenzyl)indole-3-carbaldehyde as pale yellow crystals. The yield thereof was found to be 92%. |
Here is a chemical reaction formula: Reactants are m2:N1C=C(C2=CC=CC=C12)C=O, amount is: 0.0 ;m1:[N+](=O)([O-])C1=CC=C(CBr)C=C1, 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:[N+](=O)([O-])C1=CC=C(CN2C=C(C3=CC=CC=C23)C=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 7 were repeated except for using 5.96 g of 4-nitrobenzyl bromide and 2.00 g of indole-3-carbaldehyde as a starting material to give 2.38 g of 1-(4-nitrobenzyl) indole-3-carbaldehyde as pale brown crystals. The yield thereof was found to be 62%. |
Here is a chemical reaction formula: Reactants are m1:BrCC(=O)C1=CC=CC=C1, amount is: 0.0 ;m2:N1C=C(C2=CC=CC=C12)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)C1=CC=CC=C1)N1C=C(C2=CC=CC=C12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 2.88 g of bromoacetophenone and 2.00 g of indole-3-carbaldehyde as a starting material to give 2.06 g of 1-phenacylindole-3-carbaldehyde as pale yellow crystals. The yield thereof was found to be 57%. |
Here is a chemical reaction formula: Reactants are m1:N1C=C(C2=CC=CC=C12)C=O, amount is: 0.0 ;m2:C(C1=CC=CC=C1)(C1=CC=CC=C1)Cl, 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:C(C1=CC=CC=C1)(C1=CC=CC=C1)N1C=C(C2=CC=CC=C12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 870 mg of indole-3-carbaldehyde and benzhydryl chloride in place of the benzyl bromide used in Example 1 to give 852 mg of 1-benzhydrylindole-3-carbaldehyde as brown crystals. The yield thereof was found to be 46%. |
Here is a chemical reaction formula: Reactants are m1:N1C=C(C2=CC=CC=C12)C=O, amount is: 0.0 ;m2:CS(=O)(=O)OCC1=CC=C(C=C1)OCC1=CC=CC=C1, 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:C(C1=CC=CC=C1)OC1=CC=C(CN2C=C(C3=CC=CC=C23)C=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 435 mg of indole-3-carbaldehyde and 4-benzyloxybenzyl methanesulfonate in place of the benzyl bromide used in Example 1 to give 626 mg of 1-(4-benzyloxybenzyl)indole-3-carbaldehyde as colorless crystals. The yield thereof was found to be 61%. |
Here is a chemical reaction formula: Reactants are m2:C1=CC=C(C=C1)CCBr, amount is: 0.0 ;m1:N1C=C(C2=CC=CC=C12)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(CC1=CC=CC=C1)N1C=C(C2=CC=CC=C12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 7 were repeated except for using 2.00 g of indole-3-carbaldehyde instead of the indole-4-carbaldehyde used in Example 7 and 2.35 g of 2-phenethyl bromide to give 3.34 g of 1-phenethylindole-3-carbaldehyde as a brown oily substance. The yield thereof was found to be 97%. |
Here is a chemical reaction formula: Reactants are m2:FC1=CC=C(C=C1)S(=O)(=O)Cl, amount is: 0.0 MOLE;m1:N1C=C(C2=CC=CC=C12)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:FC1=CC=C(C=C1)S(=O)(=O)N1C=C(C2=CC=CC=C12)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 17 were repeated except for using 870 mg of indole-3-carbaldehyde and 4-fluorobenzenesulfonyl chloride instead of the benzenesulfonyl chloride used in Example 17 to give 1.73 g of 1-(4-fluorobenzenesulfonyl)indole-3-carbaldehyde as brown crystals. The yield thereof was found to be 95%. |
Here is a chemical reaction formula: Reactants are m2:[H-].[Na+], amount is: 0.0 ;m3:C(C1=CC=CC=C1)Br, amount is: 0.0 ;m1_m4:N1C=CC2=CC(=CC=C12)C(=O)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)N1C=CC2=CC(=CC=C12)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Methyl indole-5-carboxylate (1.40 g) was dissolved in 10 ml of dimethylformamide, followed by addition of 212 mg of sodium hydride (content: 95%) under ice-cooling and stirring for one hour. To the mixture, there was added 1.51 g of benzyl bromide, followed by stirring the mixture for 2 hours, pouring the reaction solution into 140 ml of a 5% ammonium chloride aqueous solution and extraction with ethyl acetate (50 ml×2). The resulting organic phase was washed with water (50 ml×2), dried over anhydrous sodium sulfate and the solvent was removed through evaporation under reduced pressure to give 2.09 g of methyl 1-benzylindole-5-carboxylate as orange-colored crystals. The yield thereof was found to be 99%. |
Here is a chemical reaction formula: Reactants are m2_m5:B(Br)(Br)Br, amount is: 0.0 MOLE;m3:C(O)([O-])=O.[Na+], amount is: 0.0 MOLE;m1:C(C1=CC=CC=C1)OC1=CC=C(CN2C=C(C3=CC=CC=C23)CC2C(NC(S2)=O)=O)C=C1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m5:C(Cl)Cl, amount is: 0.0 ;m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC1=CC=C(CN2C=C(C3=CC=CC=C23)CC2C(NC(S2)=O)=O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: There was dissolved, in 30 ml of methylene chloride, 259 mg of 5-[1-(4-benzyloxybenzyl)indol-3-yl]methyl-2,4-thiazolidinedione prepared in Example 265 and the resulting solution was cooled to -78° C. After dropwise addition of a solution of boron tribromide (1.0M) in methylene chloride (10.17 ml), the temperature of the mixture was slowly raised up to room temperature. After stirring the mixture for 2 hours, a saturated sodium hydrogen carbonate aqueous solution was added followed by extraction with ethyl acetate. The resulting organic phase was washed with a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure to give 105 mg of 5-[1-(4-hydroxybenzyl)indol-3-yl]methyl-2,4-thiazolidinedione as a yellow amorphous substance. The yield thereof was found to be 51%. |
Here is a chemical reaction formula: Reactants are m1:C1C(C2=CC=CC=C2)O1, amount is: 0.0 ;m2:N1C=CC=2C(=CC=CC12)C(=O)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:OC(CN1C=CC=2C(=CC=CC12)C(=O)O)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 4.53 g of styrene oxide and 6.00 g of methyl indole-4-carboxylate as a starting material to give 5.48 g of 1-(2-hydroxy-2-phenylethyl) indole-4-carboxylic acid as a yellow amorphous substance. The yield thereof was found to be 57%. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:OC(CN1C=CC=2C(=CC=CC12)C(=O)O)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:CI, amount is: 0.0 ;m1_m2_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m5:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OC(CN1C=CC=2C(=CC=CC12)C(=O)OC)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: There were dissolved, in 80 ml of dimethylformamide, 5.39 g of 1-(2-hydroxy-2-phenylethyl)indole-4-carboxylic acid prepared in Example 319 and 3.05 g of methyl iodide, followed by further addition of 2.91 g of potassium carbonate and stirring at room temperature for 30 minutes. The reaction system was poured into 300 ml of a 10% ammonium chloride aqueous solution and extracted with ethyl acetate (100 ml×3). The resulting organic phase was washed, in order, with a 10% citric acid aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to give 5.14 g of methyl 1-(2-hydroxy-2-phenylethyl)indole-4-carboxylate as a yellow oily substance. The yield thereof was found to be 91%. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:OC(CN1C=CC=2C(=CC=CC12)C(=O)[O-])C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:N1C=NC=C1, amount is: 0.0 ;m1_m2_m3:[Si](C)(C)(C(C)(C)C)Cl, amount is: 0.0 ;m5:[OH-].[Na+], amount is: 0.0 MOLE;m4_m9:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ;m6:[F-].C(CCC)[N+](CCCC)(CCCC)CCCC, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m14:O, amount is: 0.0 ;m8:O1CCCC1, amount is: 0.0 ;m13:O, amount is: 0.0 ;m16:O, amount is: 0.0 ;m10:C(Cl)Cl, amount is: 0.0 ;m11:O1CCCC1, amount is: 0.0 ;m7:CN(C=O)C, amount is: 0.0 ;m15:O, amount is: 0.0 ;m4_m9:O1CCCC1, amount is: 0.0 ,Catalysts are m12:[O-2].[O-2].[Mn+4], amount is: 0.0 .Products are 0:OC(CN1C=CC=2C(=CC=CC12)C=O)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: There were dissolved, in 40 ml of dimethylformamide, 5.14 g of 1-(2-hydroxy-2-phenylethyl)indole-4-carboxylate prepared in Example 320, 2.37 g of imidazole and 4.50 g of t-butyldimethylsilyl chloride and the resulting solution was stirred at room temperature for 21 hours. The solution was then poured into 100 ml of water and extracted with ethyl acetate (100 ml×2). The extract was washed in order with a 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, then dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 6.97 g of a pale yellow oily substance. The substance was dissolved in 20 ml of tetrahydrofuran and then dropwise added to a suspension of lithium aluminum hydride (516 mg) in tetrahydrofuran (40 ml) with ice-cooling. After stirring at room temperature for 1.5 hour, 0.52 ml of water, 0.52 ml of a 15% aqueous sodium hydroxide solution and 1.56 ml of water were, in order, added to the mixture, followed by drying over potassium carbonate, filtration and removal of the solvent through evaporation under reduced pressure to give 6.42 g of a colorless oily substance. This substance was dissolved in 70 ml of methylene chloride, followed by addition of 37.5 g of manganese dioxide, stirring at room temperature for 17 hours, filtration through a Celite layer, removal of the solvent through evaporation under reduced pressure to give 5.1 g of a pale yellow oily substance. The substance was dissolved in 40 ml of tetrahydrofuran, followed by addition of 25.8 ml of a 1.0M tetrabutylammonium fluoride solution and stirring at room temperature for 3.5 hours. water (50 ml) was added to the solution, extracted with ethyl acetate (100 ml×2), followed by washing of the extract with, in order, 5% hydrochloric acid, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, drying over anhydrous sodium sulfate and removal of the solvent through evaporation under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography to give 3.55 g of 1-(2-hydroxy-2-phenylethyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 75%. |
Here is a chemical reaction formula: Reactants are m2_m6:OC(CN1C=CC=2C(=CC=CC12)C=O)C1=CC=CC=C1, amount is: 0.0 ;m4:[Cl-].[NH4+], amount is: 0.0 MOLE;m1:[H-].[Na+], amount is: 0.0 ;m3_m7:C(C1=CC=CC=C1)Br, amount is: 0.0 ,this reaction does not need reagents,Solvents are m2_m6:CN(C=O)C, amount is: 0.0 ;m5:CN(C=O)C, amount is: 0.0 ;m3_m7:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C1=CC=CC=C1)OC(CN1C=CC=2C(=CC=CC12)C=O)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: There was suspended 26.4 mg of 60% sodium hydride in 5 ml of dimethylformamide, followed by addition of a solution of 1-(2-hydroxy-2-phenylethyl)indole-4-carbaldehyde (160 mg) in dimethylformamide (2 ml) with ice-cooling. After stirring at room temperature for 15 minutes, the mixture was ice-cooled, then a solution of benzyl bromide (115.2 mg) in dimethylformamide (2 ml) was added thereto and stirred at room temperature for 3 hours. The reaction system was poured into 50 ml of a 10% ammonium chloride aqueous solution and extracted with ethyl acetate (50 ml×2). The resulting organic phase was washed with, in order, a 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed through evaporation under reduced pressure to give a crude product. The crude product was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to give 170 mg of 1-(2-benzyloxy-2-phenylethyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 80%. |
Here is a chemical reaction formula: Reactants are m3:C(C)N(CC)S(F)(F)F, amount is: 0.0 ;m1_m2:C(Cl)Cl, amount is: 0.0 ;m1_m2:OC(CN1C=CC2=C(C=CC=C12)CC1C(NC(S1)=O)=O)C1=CC=CC=C1, amount is: 0.0 ;m4:CO, 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:FC(CN1C=CC2=C(C=CC=C12)CC1C(NC(S1)=O)=O)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 10 ml of methylene chloride, there was dissolved 134 mg of 5-[1-(2-hydroxy-2-phenylethyl)indol-4-yl]methyl-2,4-thiazolidinedione prepared in Example 323 under an argon gas atmosphere and the resulting solution was then cooled to -34° C. After addition of 88 mg of diethylaminosulfur trifluoride to the solution and stirring it for 5 minutes and the solution was then stirred at room temperature for additional 30 minutes. After addition of 10 ml of methanol, the solution was poured into 50 ml of water and extracted with ethyl acetate. The resulting extract was dried over anhydrous sodium sulfate and the solvent was removed through evaporation under reduced pressure to give a crude product. The product was purified by preparatory silica gel thin layer chromatography (hexane:ethyl acetate=10:1) to give 98 mg of 5-[1-(2-fluoro-2-phenylethyl)indol-4-yl]methyl-2,4-thiazolidinedione as a yellow amorphous substance. The yield thereof was found to be 73%. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(Cl)Cl, amount is: 0.0 ;m1_m2_m3:OC(CN1C=CC2=C(C=CC=C12)CC1C(NC(S1)=O)=O)C1=CC=CC=C1, amount is: 0.0 ;m1_m2_m3:C(C)N(CC)CC, amount is: 0.0 ;m4:CS(=O)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC(CN1C=CC2=C(C=CC=C12)CC1C(NC(S1)=O)=O)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 10 ml of methylene chloride, there were dissolved 150 mg of 5-[1-(2-hydroxy-2-phenylethyl)indol-4-yl]methyl-2,4-thiazolidinedione prepared in Example 323 and 45 mg of triethylamine under an argon gas atmosphere and then 51 mg of methanesulfonyl chloride was added to the solution under ice-cooling. After stirring at room temperature for 30 minutes, 30 ml of ethyl acetate was added to the solution, the mixture was in order washed with a 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate and then the solvent was removed by evaporation under reduced pressure. The resulting residue was dissolved in 10 ml of dimethylformamide, followed by addition of 21 mg of lithium chloride and heating to 70° C. with stirring for 20 hours. The solution was poured into a 10% ammonium chloride aqueous solution and extracted with ethyl acetate (20 ml×3). The resulting extract was in order washed with a 10% citric acid aqueous solution, a saturated sodium hydrogen carbonate aqueous solution and a saturated common salt solution, dried over anhydrous sodium sulfate and the solvent was removed through evaporation under reduced pressure to give a crude product. The product was purified by preparatory silica gel thin layer chromatography (hexane:ethyl acetate=10:1) to give 35 mg of 5-[1-(2-chloro-2-phenylethyl)indol-4-yl]methyl-2,4-thiazolidinedione as a yellow amorphous substance. The yield thereof was found to be 22%. |
Here is a chemical reaction formula: Reactants are m2:OC(CN1C=CC=2C(=CC=CC12)C=O)C1=CC=CC=C1, amount is: 0.0 ;m1:CI, 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(CN1C=CC=2C(=CC=CC12)C=O)C1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 324 were repeated except for using 113 mg of methyl iodide and 189 mg of 1-(2-hydroxy-2-phenylethyl)indole-4-carbaldehyde prepared in Example 321 as a starting material to give 185 mg of 1-(2-methoxy-2-phenylethyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 93%. |
Here is a chemical reaction formula: Reactants are m2:C(CC1=CC=CC=C1)Br, amount is: 0.0 ;m1:N1C=CC2=CC=C(C=C12)C(=O)OC, amount is: 0.0 ;m3:C(C1=CC=CC=C1)Br, 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:C(CC1=CC=CC=C1)N1C=CC2=CC=C(C=C12)C(=O)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The same procedures used in Example 1 were repeated except for using 2.00 g of methyl indole-6-carboxylate and 2.54 g of phenethyl bromide instead of the indole-4-carbaldehyde and benzyl bromide used in Example 1 to give 0.61 g of methyl 1-phenethylindole-6-carboxylate as a yellow oily substance. The yield thereof was found to be 19%. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OC)C1)OC, amount is: 0.0 MOLE;m0_m1_m2:C(C)NC(C(Cl)(Cl)Cl)=O, 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:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=O)NCC)OC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(5-Chloro-2-methoxybenzamidomethyl)-6-(ethylaminocarbonyl-aminosulfonyl)-7-methoxychroman ##STR32## 4-(5-Chloro-2-methoxybenzamidomethyl)-6-(ethylaminocarbonyl-aminosulfonyl)-7-methoxychroman is synthesized analogously to Example 1 from 4-(5-chloro-2-methoxybenzamidomethyl)-6-sulfamoyl-7-methoxychroman and N-ethyltrichloroacetamide. Melting point: 211°-213° C. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OC)C1)OC, amount is: 0.0 MOLE;m0_m1_m2:C(CC)NC(C(Cl)(Cl)Cl)=O, 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:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=O)NCCC)OC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(5-Chloro-2-methoxybenzamidomethyl)-6-(n-propylaminocarbonyl-aminosulfonyl)-7-methoxychroman ##STR33## 4-(5-Chloro-2-methoxybenzamidomethyl)-6-(n-propylaminocarbonylaminosulfonyl)-7methoxychroman is prepared analogously to Example 1 from 4-(5Chloro-2-methoxybenzamidomethyl)-6-sulfamoyl-7-methoxychroman and N-(n-propyl)trichloroacetamide. Melting point: 159°-160° C. |
Here is a chemical reaction formula: Reactants are m1:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OC)C1)OC, amount is: 0.0 MOLE;m2:C(C)N=C=S, 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:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=S)NCC)OC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(5-Chloro-2-methoxybenzamidomethyl)-6-(ethylaminothiocarbonylaminosulfonyl)-7-methoxychroman ##STR35## 4-(5-Chloro-2-methoxybenzamidomethyl)-6-(ethylaminothiocarbonylaminosulfonyl)-7-methoxychroman is synthesize as described in Example 4 from 4-(5-chloro-2-methoxybenzamidomethyl)-6-sulfamoyl-7-methoxychroman and ethyl isothiocyanate. Melting point: 196°-197° C. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OC)C1)OC, amount is: 0.0 MOLE;m0_m1_m2:C(CC)N=C=S, 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:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=S)NCCC)OC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(5-Chloro-2-methoxybenzamidomethyl)-6-(n-propylaminothiocarbonylaminosulfonyl)-7-methoxychroman ##STR36## 4-(5-Chloro-2-methoxybenzamidomethyl)-6-(n-propylaminothiocarbonylaminosulfonyl)-7-methoxychroman is prepare from 4-(5-chloro-2-methoxybenzamidomethyl)-6-sulfamoyl-7-methoxychroman and n-propyl isothiocyanate. Melting point: 183°-184° C. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OC)C1)OC, amount is: 0.0 MOLE;m0_m1_m2:C(CCC)N=C=S, 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:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=S)NCCCC)OC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(5-Chloro-2-methoxybenzamidomethyl)-6-(n-butylaminothiocarbonylaminosulfonyl)-7-methoxychroman is prepared analogously to Example 4 from 4-(5-chloro-2-methoxybenzamidomethyl)-6-sulfamoyl-7-methoxychroman and n-butyl isothiocyanate. Melting point: 167° C. |
Here is a chemical reaction formula: Reactants are m2:CNC(C(Cl)(Cl)Cl)=O, amount is: 0.0 MOLE;m1:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OCC)C1)OC, 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:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=O)NC)OCC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(5-Chloro-2-methoxybenzamidomethyl)-6-(methylaminocarbonylaminosulfonyl)-7-ethoxychroman ##STR39## 4-(5-Chloro-2-methoxy-benzamidomethyl)-6-(methylaminocarbonylaminosulfonyl)-7ethoxychroman is prepared as described in Example 1 from 4-(5-Chloro-2-methoxybenzamidomethyl)6-sulfamoyl-7-ethoxy-chroman and N-methyltrichloroacetamide. Melting point: 207°-208° C. |
Here is a chemical reaction formula: Reactants are m1:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OCC)C1)OC, amount is: 0.0 MOLE;m2:CN=C=S, 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:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=S)NC)OCC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(5-Chloro-2-methoxy-benzamidomethyl)-6-(methylaminothiocarbonylaminosulfonyl)-7-ethoxychroman ##STR41## 4-(5-Chloro-2-methoxy-benzamidomethyl)-6-(methylaminothiocarbonylaminosulfonyl)-7-ethoxychroman is prepared as described in Example 4 from 4-(5-chloro-2-methoxybenzamidomethyl)-6-sulfamoyl-7-ethoxychroman and methyl isothiocyanate. Melting point: 202° C. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:FC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OC)C1)OC, amount is: 0.0 MOLE;m0_m1_m2:CNC(C(Cl)(Cl)Cl)=O, 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:FC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=O)NC)OC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(5-Fluoro-2-methoxybenzamidomethyl)-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman ##STR42## 4-(5-Fluoro-2-methoxy-benzamidomethyl)-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman is synthesized analogously to Example 1 from 4-(5-fluoro-2-methoxybenzamidomethyl)-6-sulfamoyl-7-methoxychroman and N-methyltrichloroacetamide. Melting point: 193°-194° C. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(N)(=O)=O)OC)=O, amount is: 0.0 MOLE;m0_m1_m2:C(C)N=C=S, 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:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(=O)(=O)NC(=S)NCC)OC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)methyl)-6-(ethylaminothiocarbonylaminosulfonyl)-7-methoxychroman ##STR48## 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-(ethylaminothio-carbonylaminosulfonyl)-7-methoxychroman is prepared analogously to Example 14 from 4-((3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-sulfamoyl-7-methoxychroman and ethyl isothiocyanate. Melting point: 147° C. |
Here is a chemical reaction formula: Reactants are m2:C(CC)N=C=S, amount is: 0.0 MOLE;m1:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(N)(=O)=O)OC)=O, 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:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(=O)(=O)NC(=S)NCCC)OC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-(n-propylaminothiocarbonylaminosulfonyl)-7-methoxychroman ##STR49## 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-(n-propylaminothiocarbonylaminosulfonyl)-7-methoxychroman is prepared as described in Example 14 from 4-((3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-sulfamoyl-7-methoxychroman and n-propyl isothiocyanate. Melting point: 96°-98° C. |
Here is a chemical reaction formula: Reactants are m2:C(C)(C)N=C=S, amount is: 0.0 MOLE;m1:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(N)(=O)=O)OC)=O, 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:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(=O)(=O)NC(=S)NC(C)C)OC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-(isopropylaminothiocarbonylaminosulfonyl)-7-methoxychroman ##STR50## 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-(isopropylaminothiocarbonylaminosulfonyl)-7-methoxychroman is synthesized following Example 14 starting from 4-((3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)methyl)6-sulfamoyl-7-methoxychroman and isopropyl isothiocyanate. Melting point: 153° C. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(N)(=O)=O)OCC)=O, amount is: 0.0 MOLE;m0_m1_m2:CN=C=S, 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:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(=O)(=O)NC(=S)NC)OCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)methyl)-6-(methylaminothiocarbonyl aminosulfonyl)-7-ethoxychroman ##STR53## 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-(methylaminothiocarbonylaminosulfonyl)-7-ethoxychroman is synthesized analogously to Example 14 from 4-((3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-sulfamoyl-7-ethoxychroman and methyl isothiocyanate. Melting point: 178° C. |
Here is a chemical reaction formula: Reactants are m3_m4:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(N)(=O)=O)OC)=O, amount is: 0.02500000037252903 MOLE;m1_m2:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(N)(=O)=O)OCC)=O, amount is: 0.0 ;m1_m2:B(Br)(Br)Br, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(N)(=O)=O)O)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Preparation of the starting compound 4-((3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-sulfamoyl-7-ethoxychroman ##STR54## 9.5 ml (0.1 mol) of boron tribromide are added dropwise to a solution of 10.6 g (0.025 mol of 4-((3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-sulfamoyl-7-methoxychroman in 75 ml of methylene chloride cooled to -10° C. After standing overnight at 20° C., the excess boron tribromide is destroyed after cooling to -10° C. by cautious dropwise addition of methanol. The mixture is then introduced into ice/water and extracted several times with methylene chloride. The combined methylene chloride extracts are dried, evaporated and recrystallized from methanol. 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-sulfamoyl-7-hydroxychroman of melting point 175° C. is obtained. |
Here is a chemical reaction formula: Reactants are m1:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(N)(=O)=O)OCC)=O, amount is: 0.0 MOLE;m2:C(C)N=C=S, 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:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(=O)(=O)NC(=S)NCC)OCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-(ethylaminothiocarbonylaminosulfonyl)-7-ethoxychroman ##STR55## 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-(ethylaminothiocarbonylaminosulfonyl)-7-ethoxychroman is synthesized analogously to Example 14, starting from 4-((3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-sulfamoyl-7-ethoxychroman and ethyl isothiocyanate. Melting point: 178°-180° C. |
Here is a chemical reaction formula: Reactants are m2:OO, amount is: 0.0 MOLE;m0_m1:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(=O)(=O)NC(=S)NC)OCC)=O, 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:C(C)C=1C(N(CC1C)C(=O)NCC1CCOC2=CC(=C(C=C12)S(=O)(=O)NC(=O)NC)OCC)=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-(methylaminocarbonylaminosulfonyl)-7-ethoxychroman ##STR56## 4-((3-Ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-(methylaminocarbonylaminosulfonyl)-7-ethoxychroman is prepared analogously to Example 18 by oxidation of 4-((3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) methyl)-6-(methylaminothiocarbonylaminosulfonyl)-7-ethoxychroman using hydrogen peroxide solution. Melting point: 187°-188° C. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OC)C1)OC, amount is: 0.0 MOLE;m0_m1_m2:CNC(C(Cl)(Cl)Cl)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:CN(C)C=O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=O)NC)OC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (+)-4-(5-Chloro-2-methoxybenzamidomethyl)-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman ##STR58## (+)-4-(5-Chloro-2-methoxybenzamidomethyl)-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman is prepared analogously to Example 1 from optically active 4-(5-chloro-2-methoxybenzamidomethyl)-6-sulfamoyl-7-methoxychroman and N-methyltrichloroacetamide. Melting point: 242° C.; [α]D20 : +63.4° (c=1, DMF); HPLC: ee 100%. |
Here is a chemical reaction formula: Reactants are m1:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OC)C1)OC, amount is: 0.0 MOLE;m2:CN=C=S, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:CN(C)C=O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=S)NC)OC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (+)-4-(5-Chloro-2-methoxy-benzamidomethyl)-6-(methylaminothiocarbonyl-aminosulfonyl)-7-methoxychroman ##STR59## (+)-4-(5-Chloro-2-methoxy-benzamidomethyl)-6-(methylaminothiocarbonylaminosulfonyl)-7-methoxychroman is prepared as described in Example 4 from optically active 4-(5-chloro-2-methoxy-benzamidomethyl)-6-sulfamoyl-7-methoxychroman and methyl isothiocyanate. Melting point: 201° C.; [α]D20 : +47.2° (c=1, DMF); HPLC: ee 88.1%. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OC)C1)OC, amount is: 0.0 MOLE;m0_m1_m2:CNC(C(Cl)(Cl)Cl)=O, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:CN(C)C=O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=O)NC)OC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (-)-4-(5-Chloro-2-methoxybenzamidomethyl)-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman ##STR60## (-)-4-(5-Chloro-2-methoxy-benzamidomethyl)-6-(methylaminocarbonyl-aminosulfonyl)-7-methoxychroman is prepared analogously to Example 1 from optically active 4-(5-chloro-2-methoxybenzamido methyl)-6-sulfamoyl-7-methoxychroman and N-methyltrichloroacetamide. Melting point: 239° C.; [α]D20 : -59.8° (c=1, DMF); HPLC: ee 98.5%. |
Here is a chemical reaction formula: Reactants are m1:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(N)(=O)=O)OC)C1)OC, amount is: 0.0 MOLE;m2:CN=C=S, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3:CN(C)C=O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:ClC=1C=CC(=C(C(=O)NCC2CCOC3=CC(=C(C=C23)S(=O)(=O)NC(=S)NC)OC)C1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: (-)-4-(5-Chloro-2-methoxybenzamidomethyl)-6-(methylaminothiocarbonylaminosulfonyl)-7-methoxychroman ##STR61## (-)-4-(5-Chloro-2-methoxybenzamidomethyl)-6-(methylaminothiocarbonyl-aminosulfonyl)-7-methoxychroman is prepared as described in Example 4 from optically active 4-(5-chloro-2-methoxybenzamidomethyl)-6-sulfamoyl-7-methoxychroman and methyl isothiocyanate. Melting point: 202° C., [α]D20 : -64.5° (c=1, DMF); HPLC: ee 97.9%. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:Cl.N[C@@H](CCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C, amount is: 0.0 ;m1_m2_m3_m4:CCN(CC)CC, amount is: 0.0 ;m1_m2_m3_m4:FC=1C=C(C(=O)Cl)C=CC1[N+](=O)[O-], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC=1C=C(C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C=CC1[N+](=O)[O-], please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of di-tert butyl L-glutamate hydrochloride (20.0 g, 67.6 mol) in Et3N (19 ml, 136.0 mmol) was added dropwise a solution of 3-fluoro,4-nitro benzoyl chloride (13.8 g, 68.0 mmol) in CH2Cl2 (300 ml). Extractive workup gave an oil (13); yield (28.0 g, 97%); 1 H NMR (Me2SO-d6) δ1.40 (s, 9H, t-Bu), 1.42 (s, 9H, t-Bu), 1.99 (m, 2H, CH2CH2CO2 -t-Bu), 2.36 (t, 2H, J=7.45 Hz, CH2CH2CO2 -t-Bu), 4.35 (m, 1H, CH), 7.92 (dd, 1H, JH-6,H-5 =7.56 Hz, H-6), 8.01 (dd, 1H, JH-2,F =11.97 Hz, H-2), 8.29 (dd, 1H, JH-5,H-6 =7.83, JH-5,F =16.10 Hz, H-5), 8.97 (d, 1H, J=7.42 Hz, NH); 9F NMR (Me2SO-d6) δ-117.98 (dd, JF,H-2 =7.32, JF,H-5 =17.8 Hz); mass spectrum (CI) m/z 427 ([M+H+ ], 100); Anal: C20H27N2O7 F-0.25CH2Cl2 requires C-54.33, H-6.19, N-6.26, F-4.24, Cl-3.96, found C-54.22, H-6.38, N-6.05, F-4.34, Cl-4.15. (The presence of CH2 Cl2 noted in the elemental analysis was confirmed by NMR). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(C1=CC=CC=C1)OC=1C=C(CO)C=CC1, amount is: 0.0 ;m1_m3_m2:C[Si](C)(C)Br, 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:C(C1=CC=CC=C1)OC=1C=C(CBr)C=CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 3-benzyloxybenzyl alcohol (9.54 g) in methylene chloride (40 ml) with TMSBr (2.5 eq, 13 mL) was heated at reflux for 1 hr. After cooling, the reaction was concentrated and then reconcentrated 2 × with methylene chloride (40 ml). The residue was chromatographed on silica gel eluting first with hexane followed by 10% methylene chloride in hexane to afford 3-benzyloxybenzyl bromide which solidifies on cooling . 5.75 g m.p. 38°-40°. |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C1=CC=CC=C1)=O, amount is: 0.0 MOLE;m0_m1_m2:C(#N)CCNN, 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:C(#N)CCNN=CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Benzaldehyde (2-cyanoethyl)hydrazone is prepared by condensation of benzaldehyde with (2-cyanoethyl)hydrazine according to the following procedure: |
Here is a chemical reaction formula: Reactants are m0_m1_m2:C(C1=CC=CC=C1)OC1=CC=C(C=O)C=C1, amount is: 0.0 MOLE;m0_m1_m2:C(#N)CCNN, 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:C(#N)CCNN=CC1=CC=C(C=C1)OCC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(benzyloxy)benzaldehyde (2-cyanoethyl)hydrazone is prepared by condensation of 4-(benzyloxy)benzaldehyde with (2-cyanoethyl)hydrazine according to the following procedure: |
Here is a chemical reaction formula: Reactants are m4_m5:C(C1=CC=CC=C1)=O, amount is: 6.0 MOLE;m0_m1_m2:C(C1=CC=CC=C1)=O, amount is: 0.0 MOLE;m0_m1_m2:OCCNN, amount is: 0.0 MOLE;m3:OCCNN, amount is: 6.0 MOLE,this reaction does not need reagents,Solvents are m4_m5:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:OCCNN=CC1=CC=CC=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: Benzaldehyde (2-hydroxyethyl)hydrazone is prepared by condensation of benzaldehyde with (2-hydroxyethyl)hydrazine according to the following procedure: 10-2 moles of (2-hydroxyethyl)hydrazine are added to a solution containing 10-2 moles of benzaldehyde in 20 ml of ethanol. The reaction is left under reflux for 30 minutes. The mixture is then cooled. The solvents are removed by evaporation. The product obtained is an extremely unstable oil. The crude reaction yield is 97%. |
Here is a chemical reaction formula: Reactants are m1_m2:FC1=C(C(=O)N)C(=CC=C1)F, amount is: 0.0 ;m1_m2:C(C(=O)Cl)(=O)Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3:ClCCCl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:FC1=C(C(=O)N=C=O)C(=CC=C1)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 0.52 g of 2,6-difluorobenzamide and 0.33 ml of oxalyl chloride was stirred under reflux in 15 ml 1,2-dichloroethane overnight. Solvent was removed under vacuum and 10 ml 1,2-dichloroethane was added. Solvent was removed under vacuum to leave the title intermediate, which could be used directly or dissolved in 1,2- dichloroethane and stored for future use. |
Here is a chemical reaction formula: Reactants are m5:NC1=CC=CC=C1, amount is: 0.0 MOLE;m6_m2_m3_m4:ClC1=C(C(=CC(=C1)N)Cl)O, amount is: 0.0 MOLE;m6_m2_m3_m4:[OH-].[K+], amount is: 0.0 ;m6_m2_m3_m4:FC(C(=C(F)F)F)(F)F, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6_m2_m3_m4:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClC=1C=C(N)C=C(C1OC(C(C(F)(F)F)F)(F)F)Cl;0:ClC=1C=C(N)C=C(C1OC(=C(C(F)(F)F)F)F)Cl, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To 1.1 liters of tetrahydrofuran containing 44.5 g of 2,6-dichloro-4-aminophenol and 3.2 g potassium hydroxide, was added subsurface 38.7 g of hexafluoropropene. The addition was complete in 25 minutes at a temperature of 8°-11° C. Analysis by liquid chromatography indicates no starting aniline present. Most of the THF was removed under vacuum, 500 mL water was added and the resulting mixture was extracted 3×500 mL ethyl ether. The combined extracts were washed with 2×100 mL 1N NaOH, 2×200 mL brine, dried over anhydrous sodium sulfate, filtered and the solvent removed under vacuum to give a mixture. This mixture was separated by prep LC to give 46.8 g of 3,5-dichloro-4-(1,1,2,3,3,3-hexafluoropropoxy)aniline and ~4 g of 3,5-dichloro-4-(1 ,2,3,3,3-pentafluoropropenoxy) aniline . Proton and 19F nmr and mass spectra were consistent with the proposed structures. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:N(=[N+]=[N-])CC(CN(S(=O)(=O)C1=CC=C(C=C1)C)CC(C)C)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3:CCO, amount is: 0.0 ,Catalysts are m1_m2_m3:[OH-].[OH-].[Pd+2], amount is: 0.0 MOLE.Products are 0:NCC(CN(S(=O)(=O)C1=CC=C(C=C1)C)CC(C)C)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of Compound 24 (2.615 g, 8.011 mmol) in EtOH (20 mL) was added Pd(OH)2 /C (1.00 g). The mixture was stirred under hydrogen atmosphere for 1 day at ambient temperature. The mixture was filtered and the filtrate concentrated to yield 2.036 g (85% yield) of a colorless oil. 1H NMR (CDCl3) 0.91 (3H, d, J=6.6 Hz), 0.91 (3H, d, J=6.6 Hz), 1.91 (1H, m), 2.43 (3H, s), 2.81 (2H, m), 2.88 (1H, dd, J=13.6, 7.3 Hz), 2.95 (1H, dd, J=12.6, 7.3 Hz), 2.99 (1H, dd, J=14.5, 7.3 Hz), 3.14 (1H, dd, J=14.8, 5.3 Hz), 3.75 (1H, m), 7.31 (2H, d, J=8.4 Hz), 7.69 (2H, J=8.4 Hz). |
Here is a chemical reaction formula: Reactants are m4_m7_m5:BrCC1=CC(=C(C=C1)OC)OC1CCCC1, amount is: 0.0 MOLE;m4_m7_m5:[C-]#N.[Na+], amount is: 0.0 ;m1_m6_m2:C1(CCCC1)OC=1C=C(C=O)C=CC1OC, amount is: 0.0 ;m1_m6_m2:[Br-].[Li+], amount is: 0.0 ;m3:C[SiH](O[SiH](C)C)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m4_m7_m5:CN(C=O)C, amount is: 0.0 ;m1_m6_m2:C(C)#N, amount is: 0.0 ;m8:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC=1C=C(C=CC1OC)CC#N, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (20 g, 90.8 mmol) in acetonitrile (100 mL) was added lithium bromide (15 g, 173 mmol) followed by the dropwise addition of trimethylsilychloride (17.4 mL, 137 mmol). After 15 min, the reaction mixture was cooled to 0° C., 1,1,3,3-tetramethyldisiloxane (26.7 mL, 151 mmol) was added dropwise and the resulting mixture was allowed to warm to room temperature. After stirring for 3 h, the mixture was separated into two layers. The lower layer was removed, diluted with methylene chloride and filtered through Celite. The filtrate was concentrated under reduced pressure, dissolved in methylene chloride and refiltered. The solvent was removed in vacuo to provide a light tan oil. To a solution of this crude a-bromo-3-cyclopentyloxy-4-methoxytoluene in dimethylformamide (160 mL) under an argon atmosphere was added sodium cyanide (10.1 g, 206 mmol) and the resulting mixture was stirred at room temperature for 18 h, then poured into cold water (600 mL) and extracted three times with ether. The organic extract was washed three times with water, once with brine and was dried (potassium carbonate). The solvent was removed in vacuo and the residue was purified by flash chromatography, eluting with 10% ethyl acetate/hexanes, to provide an off-white solid (17.7 g, 84%): m.p. 32°-34° C.; an additional quantity (1.3 g) of slightly impure material also was isolated. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:OC=1C=C(C=O)C=CC1OC, amount is: 0.0 ;m1_m2_m3_m4:ClCC1CC1, amount is: 0.0 ;m1_m2_m3_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CC1)COC=1C=C(C=O)C=CC1OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A vigorously stirred mixture of 3-hydroxy-4-methoxybenzaldehyde (20 g, 131 mmol), chloromethylcyclopropane (18.2 mL, 197 mmol) and powdered potassium carbonate (27.3 g, 197 mol) in dimethylformamide (400 mL) was heated under an argon atmosphere at 80° C. for 9 h. The mixture was allowed to cool and was filtered through Celite. The filtrate was concentrated under reduced pressure, the residue was extracted twice with ethyl acetate, the organic extract was washed five times with saturated aqueous sodium carbonate and was dried (sodium sulfate). The solvent was removed in vacuo to provide an off-white solid (21.2 g, 78%): m.p. 67°-69° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:OC=1C=C(C=O)C=CC1OC(F)F, amount is: 0.0 ;m1_m2_m4:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m3:BrCC1CC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CC1)COC=1C=C(C=O)C=CC1OC(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a mixture of 3-hydroxy-4-difluoromethoxybenzaldehyde (19.55 g, 104 mmol) and potassium carbonate (21.56 g, 156 mmol) in dimethylformamide (150 mL) under an argon atmosphere at 60° C. was added bromomethylcyclopropane (15.13 mL, 156 mmol) and the mixture was stirred and heated at 65° C. After 1.5 h, the mixture was allowed to cool and was filtered. The filtrate was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water and was extracted four times with ethyl acetate. The organic extract was washed twice with water and was dried (sodium sulfate). The solvent was removed in vacuo to provide an oil (26.4 g). |
Here is a chemical reaction formula: Reactants are m3_m5:C(#N)C(CCC(=O)OC)(CCC(=O)OC)C1=CC(=C(C=C1)OC(F)F)OCC1CC1, amount is: 0.0 ;m1_m2_m4:C(=O)(OC)C1C(CCC(C1)(C1=CC(=C(C=C1)OC(F)F)OCC1CC1)C#N)=O, amount is: 0.0 MOLE;m1_m2_m4:[H-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:COCCOC, amount is: 0.0 ;m1_m2_m4:COCCOC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CC1)COC=1C=C(C=O)C=CC1OC(F)F, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 2-Carbomethoxy-4-cyano-4-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)cyclohexan-1-one To a suspension of sodium hydride (80% dispersion in mineral oil, 11.6 g, 388 mmol) in dry 1,2-dimethoxyethane (700 mL) under an argon atmosphere was added a solution of crude dimethyl 4-cyano-4-(3-cyclopropylmethoxy-4-difluoromethoxyphenyl)pimelate (41 g) in dry 1,2-dimethoxyethane (700 mL). The resulting mixture was heated at 60° C. for 1 h, cooled to room temperature, quenched with dilute aqueous hydrochloric acid and concentrated The residue was diluted with water, was acidified to pH 3 and was extracted twice with methylene chloride. The organic extract was washed with acidic water, was dried (sodium sulfate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with methylene chloride, followed by trituration with cold ether provided a solid (17.7 g, 43% from 3-cyclopropylmethoxy-4-difluoromethoxybenzaldehyde): m.p. 115°-116° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:C(=O)(OC)C1C(CCC(C1)(C1=CC(=C(C=C1)OC(F)F)OC1CCCC1)C#N)=O, amount is: 0.0 ;m1_m2_m4_m3:CS(=O)C, amount is: 0.0 ;m1_m2_m4_m3:[Cl-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1(CCC(CC1)=O)C1=CC(=C(C=C1)OC(F)F)OC1CCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-carbomethoxy-4-cyano-4-(3-cyclopentyloxy-4-difluoromethoxyphenyl)cyclohexan-1-one (0.98 g, 2.4 mmole), dimethyl sulfoxide (10 mL), water (0.62 mL) and sodium chloride (0.62 g) under an argon atmosphere was heated at 145° C. for 5 h. The reaction mixture was cooled to room temperature and concentrated. The residue was partitioned between ether and water, the organic layer washed with water, was dried (magnesium sulfate) and the solvent was removed in vacuo. The product was purified by flash chromatography, eluting with 20-30% ethyl acetate/hexanes. The isolated residue was dissolved in ethyl acetate, this was washed twice with dilute sodium hydroxide, once with water, once with brine and then was dried and evaporated to yield a solid (0.2 g, 23.6%): m.p. 76°-78.5° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m3:C(=O)(OC)C1C(CCC(C1)(C1=CC(=C(C=C1)OC(F)F)OC1CCCC1)C#N)=O, amount is: 0.0 ;m1_m2_m4_m3:CS(=O)C, amount is: 0.0 ;m1_m2_m4_m3:[Cl-].[Na+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1(CCC(CC1)=O)C1=CC(=C(C=C1)OC(F)F)OCC1CC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 2-carbomethoxy-4-cyano-4-(3-cyclopentyloxy-4-difluoromethoxyphenyl)cyclohexan-1-one (0.5 g, 1.27 mmole), dimethyl sulfoxide (10 mL), water (1 mL) and sodium chloride (0.5 g) under an argon atmosphere was heated at 145°-150° C. for 4.5 h. The reaction mixture was cooled to room temperature and concentrated. The residue was partitioned between ethyl acetate and water, extracted twice with ethyl acetate, the organic layer was washed twice with water and once with brine, was dried (sodium sulfate) and the solvent was removed in vacuo. The product was purified by flash chromatography, eluting with 20-25% ethyl acetate/hexanes, and the resultant solid was triturated with ether/hexane and then with cold ether to provide a solid (0.22 g, 51.6%): m.p. 85.5°-86.5° C. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C(#N)C1(CCC(CC1)=O)C1=CC(=C(C=C1)OC)OC1CCCC1, amount is: 0.0 ;m1_m3_m2:Cl.NO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:N1=CC=CC=C1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1(CCC(CC1)=NO)C1=CC(=C(C=C1)OC)OC1CCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.125 g, 0.4 mmol) in pyridine (2 mL) was added hydroxylamine hydrochloride (0.031 g, 0.44 mmol), the mixture was stirred at room temperature under an argon atmosphere for 4 h and the solvent was evaporated. The mixture was partitioned between water and ethyl acetate, was extracted twice with ethyl acetate, the organic extract was dried (potassium carbonate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 25% ethyl acetate/hexanes, followed by trituration of the product with ether/hexanes provided a white solid (0.125 g, 95%): m.p. 50°-53° C. |
Here is a chemical reaction formula: Reactants are m1_m2:C(#N)C1(CCC(CC1)=O)C1=CC(=C(C=C1)OC)OC1CCCC1, amount is: 0.0 ;m1_m2:C(OC)(OC)OC, amount is: 0.0 ;m3_m4:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m3_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1(CCC(CC1)(C1=CC(=C(C=C1)OC)OC1CCCC1)C#N)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.5 g, 1.6 mmol), trimethyl orthoformate (0.21 mL, 1.9 mmol) and a catalytic amount of p-toluenesulfonic acid in methanol (20 mL) was heated gently under an argon atmosphere for 2 h. The mixture was cooled, was partitioned between aqueous sodium carbonate and ethyl acetate, was extracted twice with ethyl acetate, the organic extract was dried (potassium carbonate) and the solvent was removed in vacuo to provide an oil (0.57 g, 99%). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:COC1(CCC(CC1)(C=O)C1=CC(=C(C=C1)OC)OC1CCCC1)OC.C1(CCCC1)OC=1C=C(C=CC1OC)C1(CCC(CC1)=O)C=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(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC=1C=C(C=CC1OC)C1(CCC(CC1)=O)C=O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-formylcyclohexan-1-one 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-formylcyclohexan-1-one dimethyl ketal (0.1 g, 0.28 mmol) in ethyl acetate (2 mL) was treated with 3N hydrochloric acid (5 mnL) and the mixture was stirred vigorously and gently heated for 10 min. The mixture was extracted twice with ethyl acetate, the combined organic extracts were washed with 5% aqueous sodium carbonate, dried (potassium carbonate) and the solvent was removed in vacuo. This material, combined with that obtained from an identical reaction, was purified by flash chromatography, eluting with 2% ethyl acetate/chloroform, to provide a white solid (0.1 g, 57%): m.p. 55°-57° C. |
Here is a chemical reaction formula: Reactants are m1_m4_m2:COC1(CCC(CC1)(CO)C1=CC(=C(C=C1)OC)OC1CCCC1)OC, amount is: 0.0 ;m1_m4_m2:C(C)N(CC)S(F)(F)F, amount is: 0.0 ;m3:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m4_m2:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1(CCC(CC1)(CF)C1=CC(=C(C=C1)OC)OC1CCCC1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(hydroxymethyl)cyclohexan-1-one dimethyl ketal (0.37 g, 1.02 mmol) in methylene chloride (5 mL) was added dropwise to a solution of diethylaminosulfur trifluoride (0.14 mL, 1.02 mmol) at -78° C. under an argon atmosphere. The mixture was allowed to warm to room temperature and after 0.75 h, 5% aqueous sodium carbonate was added. The mixture was extracted with chloroform, the organic extract was dried (magnesium sulfate) and the solvent was removed in vacuo to provide a yellow oil (0.3 g, 80%). |
Here is a chemical reaction formula: Reactants are m1_m3_m2:COC1(CCC(CC1)(CF)C1=CC(=C(C=C1)OC)OC1CCCC1)OC.C1(CCCC1)OC=1C=C(C=CC1OC)C1(CCC(CC1)=O)CF, amount is: 0.0 ;m1_m3_m2:Cl, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:C(C)(=O)OCC, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(CCCC1)OC=1C=C(C=CC1OC)C1(CCC(CC1)=O)CF, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(fluoromethyl)cyclohexan-1-one 4-(3-Cyclopentyloxy-4-methoxyphenyl)-4-(fluoromethyl)cyclohexan-1-one dimethyl ketal (0.35 g, 0.95 mmol) in ethyl acetate (2 mL) was treated with 1N hydrochloric acid (2 mL) and the mixture was stirred vigorously and gently heated for 10 min. The mixture was extracted with ethyl acetate, the organic extract was washed with 5% aqueous sodium carbonate, dried (magnesium sulfate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 25% ethyl acetate/hexanes, followed by trituration with ether/hexanes, provided a white solid (0.075 g, 24%): m.p. 72°-74° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m4_m5_m3:COC1(CCC(CC1)(C1=CC(=C(C=C1)OC)OC1CCCC1)C#N)OC, amount is: 0.0 ;m1_m2_m4_m5_m3:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ;m1_m2_m4_m5_m3:OO, amount is: 0.0 ,this reaction does not need reagents,Solvents are m6:[Cl-].[Na+].O, amount is: 0.0 MOLE;m1_m2_m4_m5_m3:CO, amount is: 0.0 ;m1_m2_m4_m5_m3:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1(CCC(CC1)(C1=CC(=C(C=C1)OC)OC1CCCC1)C(=O)N)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one dimethyl ketal (0.34 g, 0.95 mmol) and powdered potassium carbonate (0.7 g, 5.1 mmol) in methanol (20 mL) and water (4 mL) at 0° C. was treated with hydrogen peroxide (30% solution, 2.55 mL). The mixture was allowed to warm to room temperature and, after seven days, brine was added and the mixture was extracted with methylene chloride. The organic extract was washed twice with brine, dried (potassium carbonate) and the solvent was removed in vacuo. Purification by flash chromatography provided the amide (0.055 g, 15%) along with recovered starting material (0.25 g). |
Here is a chemical reaction formula: Reactants are m4:C(C)(=O)O, amount is: 0.0 MOLE;m3_m6:COC1(CCC(CC1)(C=O)C1=CC(=C(C=C1)OC)OC1CCCC1)OC, amount is: 0.0 ;m1_m5_m2:CC(C)([O-])C.[K+], amount is: 0.0 ;m1_m5_m2:[N+](=[N-])=CP(OC)(OC)=O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m6:O1CCCC1, amount is: 0.0 ;m1_m5_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1(CCC(CC1)(C#C)C1=CC(=C(C=C1)OC)OC1CCCC1)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a solution of potassium t-butoxide (0.155 g, 1.38 mmol) in dry tetrahydrofuran (5 mL) under an argon atmosphere at -78° C. was added a solution of dimethyl (diazomethyl)phosphonate (ca. 88% pure, 0.24 g, 1.38 mmol). After 0.25 h, a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-formylcyclohexan-1-one dimethyl ketal (0.42 g, 1.15 mmol) in dry tetrahydrofuran (5 mL) was added dropwise and the mixture was allowed to stir at -78° C. under an argon atmosphere for 5 h. Aqueous acetic acid was added, the mixture was concentrated, partitioned between methylene chloride and water and extracted twice. The organic extract was dried (magnesium sulfate) and evaporated. Purification by flash chromatography, eluting with 3:1 hexanes/ethyl acetate, provided an oil (0.13 g, 32%). |
Here is a chemical reaction formula: Reactants are m3_m4:C1(=CC=C(C=C1)S(=O)(=O)O)C, amount is: 0.0 MOLE;m1_m2:C(#N)C1(CCC(CC1)=O)C1=CC(=C(C=C1)OC(F)F)OC(F)F, amount is: 0.0 ;m1_m2:C(OC)(OC)OC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m4:CO, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:COC1(CCC(CC1)(C#N)C1=CC(=C(C=C1)OC(F)F)OC(F)F)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-cyano-4-(3,4-bisdifluoromethoxyphenyl)cyclohexan-1-one (1.34 g, 4.05 mmol), trimethyl orthoformate (0.53 mL, 4.85 mmol) and a catalytic amount of p-toluenesulfonic acid in methanol (40 mL) was heated gently under an argon atmosphere for 2 h. The mixture was cooled and then concentrated The residue was partitioned between 5% aqueous sodium carbonate and ethyl acetate, was extracted twice with ethyl acetate, the organic extract was dried (potassium carbonate) and the solvent was removed in vacuo to provide an oil (1.5 g, 98%). |
Here is a chemical reaction formula: Reactants are m1_m5_m2_m6:COC1(CCC(CC1)(C#N)C1=CC(=C(C=C1)OC(F)F)OC(F)F)OC, amount is: 0.0 ;m1_m5_m2_m6:[H-].[Al+3].[Li+].[H-].[H-].[H-], amount is: 0.0 ;m4:C([O-])([O-])=O.[Na+].[Na+], amount is: 0.0 MOLE;m7_m3:C(=O)([O-])C(O)C(O)C(=O)[O-].[K+].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m5_m2_m6:O1CCCC1, amount is: 0.0 ;m1_m5_m2_m6:O1CCCC1, amount is: 0.0 ;m7_m3:C(C)(=O)OCC, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:COC1(CCC(CC1)(C1=CC(=C(C=C1)OC(F)F)OC(F)F)CN)OC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4-(3,4-bisdifluoromethoxyphenyl)-4-cyanocyclohexan-1-one dimethyl ketal (0.5 g, 1.33 mmol) in tetrahydrofuran (3 mL) at room temperature under an argon atmosphere was added to a suspension of lithium aluminum hydride (0.1 g, 2.66 mmol) in tetrahydrofuran (4.5 mL). After 6 h, ethyl acetate and saturated aqueous sodium potassium tartrate were added, followed by saturated aqueous sodium carbonate, and the mixture was extracted four times with ethyl acetate. The organic extract was dried (potassium carbonate) and the solvent was removed in vacuo to provide an oil (0.43 g, 85%). |
Here is a chemical reaction formula: Reactants are m1_m2_m6:C(#N)C1(CCC(CC1)=O)C1=CC(=C(C=C1)OC)OC1CCCC1, amount is: 0.0 ;m1_m2_m6:Cl, amount is: 0.0 ;m3_m4_m5_m8:C1(=CC=CC=C1)O, amount is: 0.0 MOLE;m3_m4_m5_m8:FC1=CC=C(CBr)C=C1, amount is: 0.0 ;m3_m4_m5_m8:C([O-])([O-])=O.[K+].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m9:O, amount is: 0.0 MOLE;m7:O, amount is: 0.0 MOLE;m1_m2_m6:CO, amount is: 0.0 ;m3_m4_m5_m8:CN(C=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(#N)C1(CCC(CC1)=O)C1=CC(=C(C=C1)OCC1=CC=C(C=C1)F)OC1CCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4-cyano-4-[3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.75 g, 2.4 mmol) and concentrated hydrochloric acid (2 mL) in methanol (10 mL) was heated at reflux under an argon atmosphere for 2 h. The mixture was cooled, was diluted with water and was extracted three times with methylene chloride. The organic extract was dried (magnesium sulfate) and was evaporated to the phenol (0.54 g, 92%). A vigorously stirred mixture of this phenol, 4-fluorobenzyl bromide (0.83 mL, 6.6 mmol) and potassium carbonate (0.92 g, 6.6 mmol) in dimethylformamide (12 mL) was heated under an argon atmosphere at 90° C. for 2 h. The mixture was allowed to cool, was diluted with water and was extracted three times with ether. The organic extract was dried (magnesium sulfate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 30% ethyl acetate/hexanes, provided a white solid (0.6 g, 78%): m.p. 145°-146° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(#N)C1(CCC(CC1)=O)C1=CC(=C(C=C1)OCC1=CC=C(C=C1)F)OC1CCCC1, amount is: 0.0 ;m1_m2_m3:Cl.NO, amount is: 0.0 ,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:C(#N)C1(CCC(CC1)=NO)C1=CC(=C(C=C1)OCC1=CC=C(C=C1)F)OC1CCCC1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 4-cyano-4-[3-cyclopentyloxy-4-(4-fluorobenzyloxy)phenyl)cyclohexan-1-one (0.525 g, 1.49 mmol) and hydroxylamine hydrochloride (0.114 g, 1.63 mmol) in pyridine (5 mL) was was stirred at room temperature under an argon atmosphere for 18 h. The mixture was partitioned between 1N hydrochloric acid and methylene chloride, the organic extract was dried (magnesium sulfate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 35% ethyl acetate/hexanes, provided a white solid (0.45 g, 82%): m.p. 55°-57° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m4:C(=O)(OC)C1C(CCC(C1)(C1=CC(=C(C=C1)OC)OCC1CC1)C#N)=O, amount is: 0.0 ;m1_m2_m4:[H-].[Na+], amount is: 0.0 ;m3:ClCOC, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m4:CN(P(N(C)C)(N(C)C)=O)C, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(=O)(OC)C1=C(CCC(C1)(C1=CC(=C(C=C1)OC)OCC1CC1)C#N)OCOC, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A solution of 2-carbomethoxy-4-cyano-4-(3-cyclopropylmethoxy-4-methoxyphenyl)cyclohexan-1-one (1.0 g, 2.8 mmol) and sodium hydride (80% dispersion in mineral oil, 0.09 g, 3.1 mmol) in dry hexamethylphosphoric triamide (8 mL) was stirred under an argon atmosphere at room temperature for 0.5 h. Chloromethylmethyl ether (0.26 mL, 3.4 mmol) was added and stirring was continued for 4.5 h. The mixture was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, was extracted three times, the organic layer was dried (sodium sulfate) and the solvent was removed in vacuo. The product was purified by flash chromatography, eluting with 3:1 hexanes/ethyl acetate, to provide a white solid (0.5 g, 44%): m.p. 98°-99° C. |
Here is a chemical reaction formula: Reactants are m1_m2:OC1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1_m2:CO, amount is: 0.0 ;m4:C(C=C)Br, amount is: 0.0 ;m3_m5:[OH-].[K+], amount is: 0.0 ,this reaction does not need reagents,Solvents are m3_m5:O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(C=C)OC1=CC=C(C(=O)O)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: 4-(2-Propenyloxy)benzoic acid was synthesized by Apfel's method (Apfel et al, Anal. Chem., 1985, 57, 651-658). A 1 L three-neck round-bottom flask was equipped with a condenser, 150 mL additional funnel, heating bath, and magnetic stirrer. 90 g (0.65 mol) of 4-hydroxybenzoic acid and 400 mL of methanol were added at 25° C. and stirred. After the acid was dissolved, 105 g (1.9 mol) of potassium hydroxide in 125 mL of distilled water was added dropwise. The reaction mixture was heated to reflux, and 90 g (0.74 mol) of allyl bromide was then added over a 2 hour period. The reaction mixture was allowed to reflux for 8 hours. As the reaction proceeded, potassium bromide precipitated. From this mixture, 250 mL of methanol was removed by evaporation. The remainder of the reaction mixture was cooled to 25° C. and then added to 2.5 L of distilled water. Hexane (250 mL) was added to extract organic impurities. After discarding the organic phase, the aqueous phase was heated to 40° C. and neutralized with 300 mL of 20% HCl. The crude product precipitated during the neutralization, was subsequently collected by filtration and purified by recrystallization from ethanol. Yield: 46 g (40.2%), mp 165° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(C=C)OC1=CC=C(C(=O)O)C=C1, amount is: 0.0 MOLE;m1_m2_m3:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m2_m3:N1=CC=CC=C1, amount is: 0.0 MOLE.Products are 0:C(C=C)OC1=CC=C(C(=O)Cl)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The 4-(2-propenyloxy)benzoic acid, 5 g (0.028 mol), was refluxed with thionyl chloride (37 mL, 0.51 mol) and several drops of pyridine for 8 hours. The excess thionyl chloride was removed in vacuo leaving 4-(2-propenyloxy)benzoyl chloride as a yellow liquid at 25° C. This acid chloride was used without further purification. |
Here is a chemical reaction formula: Reactants are m1_m2_m3:C(CCCC=C)OC1=CC=C(C(=O)O)C=C1, amount is: 0.0 ;m1_m2_m3:S(=O)(Cl)Cl, amount is: 0.0 ,this reaction does not need reagents,this reaction does not need solvents,Catalysts are m1_m2_m3:N1=CC=CC=C1, amount is: 0.0 MOLE.Products are 0:C(CCCC=C)OC1=CC=C(C(=O)Cl)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: The 4-(5-hexenyloxy)benzoic acid 10 g (0.046 mol) was reflux with thionyl chloride (5.4 mL, 0.069 mol) and several drops of pyridine for 8 hours. The excess thionyl chloride was removed in vacuo leaving 4-(5-hexenyl-oxy)benzoyl chloride as a clear liquid at 25° C. This acid chloride was used without further purification. |
Here is a chemical reaction formula: Reactants are m1_m3_m2:C1(=CC=CC=C1)S(=O)(=O)NN=C(C1=C(C=CC=C1)Br)Cl, amount is: 0.0 ;m1_m3_m2:CN1CCNCC1, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m3_m2:O1CCCC1, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C1(=CC=CC=C1)S(=O)(=O)NN=C(N1CCN(CC1)C)C1=C(C=CC=C1)Br, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution, under nitrogen, of α-chloro-2-bromobenzaldehyde phenylsulfonylhydrazone (271.1 g; 720 mmol) in tetrahydrofuran (THF; 2 L), was added dropwise N-methylpiperazine (159.7 g; 1600 mmol). The reaction was stirred at ambient temperature for three hours, and then permitted to stand at ambient temperature for 16 hours. The reaction was chilled in an ice bath, and then filtered to remove the piperazine hydrochloride that was formed. The filtrate was concentrated to yield a brown gum. The gum was triturated with hot acetonitrile, the mixture was cooled in an ice bath, and when cold, was filtered to remove unwanted side product. The filtrate was then concentrated to afford 392.9 g of a brown gum of crude 1-[[(phenylsulfon-yl)hydrazono]-(2-bromophenyl)methyl]-4-methylpiperazine. |
Here is a chemical reaction formula: Reactants are m1_m3:N1N=C(C2=CC=CC=C12)N1CCN(CC1)C#N, amount is: 0.0 ;m2:[OH-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m3:OS(=O)(=O)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:N1(CCNCC1)C1=NNC2=CC=CC=C12, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A mixture of 4-(1H-indazol-3-yl)-1-piperazinecarbonitrile (8.0 g, 40 mmol) and 25% H2SO4 (100 ml) was stirred at reflux for 4.5 hours. The reaction was cooled in an ice bath and made basic by the dropwise addition of 50% NaOH. The basic solution was extracted with ethyl acetate. The ethyl acetate was washed with H2O, dried with MgSO4, and concentrated to afford 5.2 g (73% of the desired compound, as a solid. The solid was recrystallized twice from toluene to afford 3.0 g of 3-(1-piperazinyl)-1H-indazole, m.p.=153°-155° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:Cl.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:ClCCCOC1=C(C=C(C=C1)C(C)=O)OC, amount is: 0.0 ;m1_m2_m3_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=C(C=C2)C(C)=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2 benzisoxazole hydrochloride (5.1 g, 20 mmol), K2CO3 (5.2 g, 40 mmol), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]-ethanone (5.3 g, 22 mmol), and dimethylformamide (60 ml) was heated at 90° C. for 16 hours. The reaction was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate was washed (water), dried (MgSO4) and concentrated to afford a moist solid. Recrystallization (twice) from ethyl alcohol afforded 5.0 g (58%) of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperdinyl]propoxy]-3-methoxyphenyl]-ethanone as a beige solid, m.p.=118°-120° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m4:Cl.FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m4:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m4:BrCCCCOC1=C(C=C(C=C1)C(C)=O)OC, amount is: 0.0 ;m1_m2_m3_m4:CN(C=O)C, amount is: 0.0 ,this reaction does not need reagents,Solvents are m5:O, amount is: 0.0 MOLE,this reaction does not need catalysts,Products are 0:FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCCOC2=C(C=C(C=C2)C(C)=O)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (5.1 g, 0.02 mol), K2CO3 (5.2 g, 0.04 mol), 1-[4-(4-bromobutoxy)-3-methoxyphenyl]ethanone (6.6 g, 22 mmol), and dimethylformamide (60 ml) was heated at 75° C. for 5 hours. The reaction was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate was washed (water), dried (MgSO4), and the solvent was concentrated to yield initially an oil, which solidified upon standing. The solid was triturated with hexane and collected to afford 7.7 g of the product as a waxy solid. The compound was chromatographed on a Waters Prep 500 utilizing silica gel columns and eluting with dichloromethane/methanol (5%). Concentration of the appropriate fractions yielded 5.1 g of off-white solid 1-[4-[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-butoxy]-3-methoxyphenyl]ethanone, which when recrystallized from ethyl alcohol yielded 3.2 g (36%) of feathery-white needles, m.p.=88°-90° C. |
Here is a chemical reaction formula: Reactants are m6:C(=O)(O)[O-].[Na+], amount is: 0.0 MOLE;m4:B(Br)(Br)Br, amount is: 0.0 MOLE;m1_m7_m2:ClCCCOC1=C(C=C(C=C1)C(C)=O)OC, amount is: 0.0 ;m1_m7_m2:C(=O)=O.CO, amount is: 0.0 MOLE;m3:B(Br)(Br)Br, amount is: 0.0 MOLE;m5:C(=O)(O)[O-].[Na+], amount is: 0.0 MOLE,this reaction does not need reagents,Solvents are m1_m7_m2:C(Cl)Cl, amount is: 0.0 ;m8:C(Cl)Cl, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:ClCCCOC1=C(C=C(C=C1)C(C)=O)O, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: To a stirred solution of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (10.0 g, 41 mmol) in methylene chloride (120 ml) cooled to -50° C. (dry ice-methanol) was added, dropwise, 1M boron tribromide in methylene chloride (123 ml, 120 mmol). The temperature was kept between -40° C. and -50° C. After complete addition, the reaction was permitted to reach -30° C., and the TLC checked (ca. 15 min. after final boron tribromide was added). Saturated NaHCO3 was added, dropwise, never to allowing the temperature to go above 0° C. during most of the addition. When sufficient NaHCO3 had been added to make the solution basic, the organic layer was collected. The layer was washed with brine, dried (MgSO4), and concentrated to yield 8.1 g of dark brown oil, which solidified on standing. This was chromatographed on a Waters Prep 500 LC (2 silica columns, 2% methanol-methylene chloride as eluent). Upon concentration of the appropriate fractions, 5.8 g of a brown tacky solid were obtained. This was recrystallized from isopropyl ether (with decanting of the yellow isopropyl ether supernatant from the dark brown oily residue) to give initially 2.5 g of a yellow solid. Concentration of the mother liquor gave an additional 0.5 g, m.p.=110°-113° C. |
Here is a chemical reaction formula: Reactants are m1_m2_m3_m5:FC1=CC2=C(C(=NO2)C2CCNCC2)C=C1, amount is: 0.0 ;m1_m2_m3_m5:C(=O)([O-])[O-].[K+].[K+], amount is: 0.0 ;m1_m2_m3_m5:COC1=C(OCCCCl)C=CC=C1, amount is: 0.0 ;m4_m6:C(\C=C\C(=O)O)(=O)O, amount is: 0.0 ,this reaction does not need reagents,Solvents are m1_m2_m3_m5:C(C)#N, amount is: 0.0 ;m4_m6:C(C)O, amount is: 0.0 ,this reaction does not need catalysts,Products are 0:C(\C=C\C(=O)O)(=O)O.FC1=CC2=C(C(=NO2)C2CCN(CC2)CCCOC2=C(C=CC=C2)OC)C=C1, please give me the reaction condition of this chemical formula. | The condition of this chemical reaction is: A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (2.45 g; 11.1 mmol), K2CO3 (2.0 g), and 3-(2-methoxyphenoxy)propyl chloride (3.5 g, 17.4 mmol) in acetonitrile (40 ml) was heated at 90° C. for 4 hours. At the end of the reaction, the solvent was removed, and the solids were dissolved into dichloromethane (100 ml). The solution was washed with water and brine, then dried over MgSo4. The crude material from the solution was combined with 1.2 g of crude material prepared in the same fashion (using 0.5 g of starting material). The combined material was purified by flash chromatography on a silica gel column (49 g, eluted with 0.5% diethylamine:1% methanol:98.5% dichloromethane, 1 L). The fractions containing the pure product were pooled and concentrated down to a light oil (3.68 g). This oil was treated with fumaric acid (1.14 g, 9.8 mmol) in ethanol (13 ml). The 6-fluoro-3-[1-[3-(2-methoxyphenoxy)-propyl]-4-piperidinyl]-1,2-benzisoxazole fumarate crystals obtained weighed 4.01 g (60%), m.p.=169°-170° C. |