Benzocaine → 4-{[1-(3-Bromo-5-chloro-phenyl)-methylidene]-amino}-benzoic acid ethyl ester

Participants

Reaction Steps

A mixture of 4-amino-benzoic acid ethyl ester (8.3 g, 50.3 mmol) and 3-bromo-5-chloro-benzaldehyde (11.0 g, 50.3 mmol) in ethanol (100 mL) was heated to reflux for 2 hours. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 4-{[1-(3-bromo-5-chloro-phenyl)-methylidene]-amino}-benzoic acid ethyl ester (6.4 g, 35%) as a white solid: LC/MS m/e calcd for C16H13BrClNO2 M+: 366.6, observed: 366.6.

Provenance & Evidence