Syntheses of N-Vinylphthalimide Derivatives

Halogenation and its Reaction

Abstract

Reaction of chlorine and N-vinylphthalimide (1) at low temperature gives N-(1, 2-dichloroethyl)-phthalimide (2) and N-(2-chloroviny1)-phthalimide (3), with melting point 94.5-95.5° and 101.5-402.5°C, respectively.(2) and alcohol give an ether and the methyl ether gives off alcohol by sodium hydrogen sulfate and yields (3).
N-(1, 2-Dibromoethyl)-phthalimide and alcohol give an ether. Also, N-(1-methoxy-2-iodoethyl)-phthalimde can be synthesized with good yield from mercuric acetate addition product of (1)
N-(1-Chloroethyl)-phthalimide and ethanolamine caused imide-exchange reaction and gave N-(2-hydroxyethyl)-phthalimide.