Ionic liquid enabled sulfamoylation of arenes: an ambient, expeditious and regioselective protocol for aryl sulfonamides

The ionic liquid, 1-butyl-3-methylimidazolium chloroaluminate, [bmim]Cl.AlCl3, N=0.67 mediated syntheses of aromatic sulfonamides via electrophilic substitution of arenes is reported. The protocol serves as a distinctly expeditious and ambient route towards the syntheses of these pharmaceutically useful compounds, yielding quantitative conversions at room temperature within 5-30 min in most of the cases. The Lewis acidity and molar stoichiometry of the ionic liquid influences the extent of conversion. The method has been used for the syntheses of a diverse range of sulfonamides by variation of arenes and sulfamoyl chlorides. With monosubstituted benzenes, the protocol offers an added advantage of exclusive selectivity towards the formation of para substituted sulfonamides over the ortho products. (C) 2004 Elsevier Ltd. All rights reserved.