ANTINEOPLASTIC AGENTS: XV. INTRAMOLECULAR REACTIONS OF N-PHENYL-N′-BIS(2-CHLOROETHYL)UREA

Abstract

Reaction between phenyl isocyanate and N-bis(2-chloroethyl)amine in cold diethyl ether solution yields N-phenyl-N′-bis(2-chloroethyl)urea. The urea was found to rearrange in ethanol solution or upon warming to, respectively, 2-(N-phenylimino)-3-(2′-chloroethyl)oxazolidine hydrochloride and 1-phenyl-2-oxo-3-(2′-chloroethyl)imidazolidine. Infrared spectral studies, augmented by mass and proton magnetic resonance determinations provided compelling support for the structural formulations. The oxazolidine reaction sequence was also examined employing 4-nitrophenyl isocyanate, 1-naphthyl isocyanate, and N-bis(2-bromoethyl)amine.