Organic Chemistry Portal



Carbamoylimidazolium and thiocarbamoylimidazolium salts: novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides

Justyna A. Grzyb, Ming Shen, Chiaki Yoshina-Ishii, W. Chi, R. Stanley Brown and Robert A. Batey*

*Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ont., Canada M5S 3H6, Email:

J. A. Grzyb, M. Shen, C. Yoshina-Ishii, W. Chi, R. S. Brown, R. A. Batey, Tetrahedron, 2005, 61, 7153-7175.

DOI: 10.1016/j.tet.2005.05.056

see article for more examples


Readily prepared carbamoylimidazolium salts act as efficient N,N-disubstituted carbamoylating reagents, as a result of the ‘imidazolium' effect. The salts react with amines, thiols, phenols/alcohols, and carboxylic acids in high yields, without the need for subsequent chromatographic purification of the products, producing ureas, thiocarbamates, carbamates, and amides, respectively.

see article for more reactions

see article for more examples

Key Words

carbamoylimidazolium salts, thiocarbamoylimidazolium salts, ureas, thioureas, carbamates, thiocarbamates, amides

ID: J72-Y2005-2990