Toluene → HCID 68488483, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(ethylthio)acrylic acid (5.67 g) in toluene (50 mL) were added thionyl chloride (3.48 mL) and DMF (catalytic amount) at room temperature, and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added acetonitrile (50 mL), and then was added dropwise a solution of aniline (8.78 g) in acetonitrile (10 mL) under ice-cooling. The mixture was stirred at the same temperature for 1 hour and then at room temperature for 3 hours, and then concentrated under reduced pressure. To the residue was added 1N hydrochloric acid (50 mL), and the mixture was stirred at room temperature for 0.5 hour. The formed crystals were collected by filtration, washed with water, filtered, and then dried to obtain 3-(ethylthio)-N-(phenyl)acrylamide (8.03 g) as a white crystal.

Provenance & Evidence