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Simple and convenient synthesis of tertiary benzanilides using dichlorotriphenylphosphorane

Isao Azumaya*, Takako Okamoto, Fumiaki Imabeppu and Hiroaki Takayanagi

*School of Pharmaceutical Sciences, Kitasato University, Tokyo 108-8641, Japan, Email:

I. Azumaya, T. Okamoto, F. Imabeppu, H. Takayanagi, Tetrahedron, 2003, 59, 2325-2331.

DOI: 10.1016/S0040-4020(03)00235-7


Various tertiary benzanilide derivatives were effectively synthesized in high yields from a broad range substituted benzoic acid and N-monoalkylated anilines using dichlorotriphenylphosphorane in chloroform. Allyl, Boc, MPM and the Z group were unaffected under these conditions.

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proposed mechanism

Key Words

amides, coupling reagent, cyclic amides

ID: J72-Y2003-480