Ethylamine → (2E)-3-(3-Bromophenyl)-N-ethyl-2-propenamide

Participants

Reaction Steps

A solution of trans 3-bromocinnamoyl chloride (12.3 g) in anhydrous toulene (150 ml) was added slowly with stirring to a solution of ethylamine (10 g) in dry ether (100 ml) at room temperature. The reaction mixture was heated at reflux for one hour, and the solvent and excess amine were then removed under reduced pressure. The residue was triturated with water, filtered, and recrystallized from ethanol-water to give trans 3-bromo-N-ethylcinnamamide, m.p. 89°-90° C., as a white crystalline material. NMR and IR spectra as well as elemental analysis were consistent with the assigned structure.

Provenance & Evidence