Novel Synthesis of Mafenide and Other Amino Sulfonamides by Electrochemical Reduction of Cyano Sulfonamides

✍ Scribed by Shaik Lateef; Srinivasulu Reddy Krishna Mohan; Rudraraju Rameshraju; Srinivasulu Reddy Jayarama Reddy

• Book ID: 102253406
• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: German
• Weight: 59 KB
• Volume: 89
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200690123

✦ Synopsis

Abstract

Both aliphatic and aromatic amino sulfonamides such as mafenide (1a) were synthesized in good yields (80–86%) by direct electrochemical hydrogenation of the corresponding nitriles in an undivided cell containing a Ni cathode, a Pt anode, and Raney Ni as catalyst (Table 1). The reaction can be performed without external supply of pressurized gas by in situ generation of H~2~. Slightly elevated temperatures (45°) and low current densities (10 mA/cm^2^) are favorable conditions for this type of electrochemical nitrile hydrogenation. Our synthetic protocol does not require high‐pressure equipment or chemical hazards, is environmentally very friendly, and more economical than traditional methods. The concentration of adsorbed H^.^ radicals on the catalyst surface can be easily controlled by adjusting the electric potential, which may lead to improved product selectivity and, at the same time, reduces the risk of explosion and fire.