p-Toluenesulfonic acid → 2-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide

Participants

Reaction Steps

540 mg (2.49 mmol) of 3-oxo-N-(3-phenyl-2-propene-1-yl)butyramide, 0.28 ml (2.47 mmol) of 3-chlorobenzaldehyde and 0.05 ml (0.51 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 water was removed. Ethyl acetate was added to the reaction mixture. After washing with 2 N hydrochloric acid and then with a saturated aqueous sodium hydrogencarbonate solution, the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 2-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide. The title compound was obtained from this compound and 212 mg (2.58 mmol) of 3-aminocrotonitrile in the same manner as that of Example 1-3).

Provenance & Evidence