Efficient Large-Scale Synthesis of 2-Amino-5-methanesulfonylaminobenzenesulfonamide

Abstract

A novel synthesis of 2-amino-5-methanesulfonylaminobenzenesulfonamide is described. This preparation begins with readily available 4-nitroaniline and proceeds through five steps (isolations) in 41% overall yield. The described chemistry is conducted on a 50- to 100-g scale and does not require extractive workup procedures or chromatographic purifications.

Keywords:

• 2-Amino-5-methanesulfonylaminobenzenesulfonamide
• Friedel–Crafts acylation
• Sulfonamide

ACKNOWLEDGMENT

The authors thank Drs. David Kucera, Jerry (Lijian) Chen, and David Ellis for many helpful discussions during the course of this work.