p-Toluenesulfonic acid → HCID 4457426、化合物

反応式

[C:1]([NH2:7])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Cl:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O.N1CCCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[C:3]([C:2](=[CH:12][C:11]1[CH:14]=[CH:15][CH:16]=[C:9]([Cl:8])[CH:10]=1)[C:1]([NH2:7])=[O:6])(=[O:4])[CH3:5]

参加物

実験手順

208 mg (2.06 mmol) of acetoacetamide, 0.23 ml (2.00 mmol) of 3-chlorobenzaldehyde and 0.02 ml (0.20 mmol) of piperidine were heated under reflux in the presence of a catalytic amount of p-toluenesulfonic acid in 30 ml of benzene overnight while removing water. Ethyl acetate was added to the reaction mixture and they were washed with 1 N hydrochloric acid and then with saturated aqueous sodium hydrogencarbonate solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 2-acetyl-3-(3-chlorophenyl)acrylamide. 10 ml of 2-propanol and 486 mg (1.65 mmol) of (3,3-diphenylpropane-1-yl)3-aminocrotonate were added to the obtained product, and they were stirred under heating at 80° C. overnight. 2-Propanol was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (hexane/ethyl acetate=1/2) to obtain the title compound.