Improved Oxidation of the Sulfenamide Functionality: Efficient Synthesis of 6-Ethoxy-2-Benzothiazolesulfonamide

Abstract

The sulfonamide group is an important functionality found in many medicinals: antibiotics, diuretics, and antiglaucoma agents to name a few.¹ Generally, the sulfonamide group is attached to an aryl or heterocyclic ring, and is prepared by amidation of the corresponding sulfonyl chloride² or oxidation of a sulfenamide precursor.³ In developing an efficient synthesis of 6-ethoxy-2-benzothiazolesulfonamide 1 we have broadened the use of the peracids, m-chloroperoxybenzoic acid (MCPBA) and peracetic acid, to the sulfenamide-sulfonamide oxidation.