Synthesis 2002(1): 0029-0030
DOI: 10.1055/s-2002-19312
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

Can N-Alkyl- and N-Arylimidazoles be Prepared Directly from Alcohols and Phenols with N,N’-Carbonyldiimidazole?

Walter Fischer*
Ciba Specialty Chemicals, R&D Segment Coating Effects, WRO 1059.505, P.O.Box, CH-4002 Basel, Switzerland
Fax: +41(61)6362115; e-Mail: walter.fischer@cibasc.com;
Further Information

Publication History

Received 27 August 2001
Publication Date:
04 August 2004 (online)

Abstract

The report that N-alkyl- and N-arylimidazoles can be prepared directly by reactions of N,N’-carbonyldiimidazole (CDI) with alcohols or phenols was shown to be erroneous. Under the described conditions only (N-alkoxy-carbonyl)- and (N-aryloxy-carbonyl)-imidazoles (carbamates) were obtained.

    References

  • 1 Njar VCO. Synthesis  2000,  2019 
  • 2 Johnson AL. inventors; US Patent, 3 637  731.  (filed 1968)
  • 3 Ethyl imidazole-1-carboxylate, e.g., exhibits a C=O stretch band at 1750 cm-1: Pouchert CJ. In The Aldrich Library of Infrared Spectra   Aldrich; USA: 1981.  Ed. III. p.1223F 
  • 4a Pouchert CJ. Behnke J. In The Aldrich Library of 13 C and 1 H FT NMR Spectra   Ed. I, Vol. 3:  Aldrich; USA: 1993.  p.81C 
  • 4b Pouchert CJ. Behnke J. In The Aldrich Library of 13 C and 1 H FT NMR Spectra   Ed. I, Vol. 3:  Aldrich; USA: 1993.  p.76A 
  • 4c Pouchert CJ. Behnke J. In The Aldrich Library of 13 C and 1 H FT NMR Spectra   Ed. I, Vol. 3:  Aldrich; USA: 1993.  p.77C 
  • 4d Pouchert CJ. Behnke J. In The Aldrich Library of 13 C and 1 H FT NMR Spectra   Ed. I, Vol. 3:  Aldrich; USA: 1993.  p.79B 
  • 4e Pouchert CJ. Behnke J. In The Aldrich Library of 13 C and 1 H FT NMR Spectra   Ed.I, Vol. 3:  Aldrich; USA: 1993.  p.86B