THE REACTION OF SOME AROMATIC ACIDS WITH SODIUM AZIDE IN A TRIFLUOROACETIC ACID – TRIFLUOROACETIC ANHYDRIDE MEDIUM

Some commercially available aromatic acids have been treated with sodium azide using a mixture of trifluoroacetic acid and trifluoroacetic anhydride as the reaction medium. Benzoic, ortho-, meta-, and para-toluic, ortho-bromo-, and ortho-nitro-benzoic acids were converted to corresponding N-substituted trifluoroacetamides in good yields. 1-Naphthoic acid was converted to N-(1-naphthyl)-trifluoroacetamide in near quantitative yield. Meta- and para-bromobenzoic and meta- and para-nitrobenzoic acids did not undergo this modified Schmidt reaction under these conditions. The conversion of aromatic acids to N-substituted trifluoroacetamides is discussed and evidence is presented for the mechanism.