Sodium Bicarbonate → (E)-N-[2-(3,4-dimethoxyphenyl)-2-(methylthio)ethyl]-3-(3-pyridyl)-2-propenamide

Participants

Reaction Steps

To a solution of the crude oily 2-(3,4-dimethoxy-phenyl) -2-(methylthio)ethylamine (0.96 g) and trans-3-(3-pyridyl) acrylic acid (0.63 g, 4.2 mmol) in dimethylformamide (10 ml), diethylphosphoric cyanide (0.69 ml) and triethylamine (1.17 ml) were sequentially added under ice-cooling and stirred for 10 minutes under ice-cooling. Aqueous sodium bicarbonate solution was added to the reaction mixture and extracted with ethyl acetate. The organic layers were combined, washed with water and aqueous saturated sodium chloride solution and dried over magnesium sulfate. The solvent was distilled out under reduced pressure and the residue was purified by silica gel column chromatography (hexane: chloroform:ethanol=8:2:1) to yield the titled compound (788 mg, 47%).

Provenance & Evidence