Studies of N-Sulfinyl Compounds. VI. The Preparation of N-Sulfinylbenzamide and Its Reaction with Styrene Oxide

Abstract

Abstract The reaction of benzamide with thionyl chloride in the presence of pyridine gave N-sulfinylbenzamide and N,N′-dibenzoylsulfurdiimide. It has been found that N-sulfinylbenzamide reacted with styrene oxide in the presence of tetraethylammonium bromide to give 4-oxo-5-benzoyl-2,6-diphenyl-1,4,3,5-oxathiadiazepine as the main product, accompanied by lesser quantities of two N-benzoyl-phenylaminoethanols, 2,5-diphenyloxazoline, benzonitrile, and benzamide. The pathways for the formation of the products are suggested.