Benzene → N-(1-Methylethyl)-3-Chlorocinnamoylcarboxamide

Participants

Reaction Steps

A mixture of 3-chlorocinnamic acid (25 g.), thionyl chloride (19.4 g.) and benzene (300 ml.) was heated under reflux for 2 hours, then evaporated under reduced pressure on a rotary evaporator to give an oil. The oil was dissolved in benzene (50 ml.), and the benzene solution was added slowly to a mixture of isopropylamine (25 g.) and benzene (300 ml.). The resulting mixture was allowed to stir at room temperature for 2 hours, and heated under mild reflux for 1 hour. It was then allowed to set at room temperature overnight. The precipitate thus separated was collected on a filter, and washed with benzene. The combined filtrate and washings were washed with water, then dried over potassium carbonate. Removal of benzene under reduced pressure on a rotary evaporator gave an oil which solidified on standing. The product melted at 92°-94°, and weighed 28 g.

Provenance & Evidence