Reaction of Phenyl Isocyanate with 2,3-Epoxy Propyl Phenyl Ether (Phenyl Glycidyl Ether)

Abstract

REACTION of phenyl isocyanate and 2,3-epoxy propyl phenyl ether gives a one-to-one addition compound, and there is evidence to suggest this is 3 phenyl 5 phenoxy methyl 2 oxazolidono. The reaction is believed to be: This is similar to a reaction reported by A. Thompson¹ between acidulated potassium cyanate and epichlorhydrin. Evidence for the foregoing scheme is: (1) Reaction with alcoholic potash yielded a compound in agreement with the reaction: The product of this reaction gave a yellow oil on reaction with nitrous acid, suggesting a secondary amine. (2) There was no reaction of the reaction product with nitrous acid. The nitrogen of this compound is thus not present in the form of a primary or secondary amine. (3) The product of the reaction was broken down by heating with concentrated hydrochloric acid in a sealed tube at 200° C to give an oil, which was shown to be a chlorine containing compound. This is in agreement with the concept of acid hydrolysis of the oxazolidone ring.