
%0 Journal Article
%A Rosevear, J 
%A Wilshire, JFK 
%T A Comparison of the Reactions of Some Ethyl N-Arylcarbamates With Those of the Corresponding Acetanilides. II. Amidomethylation With N-Hydroxy-methylphthalimide
%J Australian Journal of Chemistry
%D 1990/02/01
%V 43
%N 2
%P 339-353
%K 
%R https://doi.org/10.1071/CH9900339
%U https://www.publish.csiro.au/paper/CH9900339 
%X The reactions of some ethyl N- arylcarbamates and of the corresponding acetanilides towards 1 equiv. of N-hydroxymethylphthalimide in concentrated sulfuric acid at 50&#176; have been compared with one another. In the case of certain para-substituted compounds, amidomethylation occurs more readily ortho to the carbamate group than to the N-acetyl group. The diagnostic use of (D6)benzene as a 1H n.m.r. solvent, particularly for the structural elucidation of the ortho-( phthalimidomethyl )- phenylcarbamates and -acetanilides, is reported. Acidic treatment of the ortho -( phthalimidomethyl ) phenylcarbamates, but not of the corresponding acetanilides, gave 8-substituted isoindolo [1,2-b]quinazolin-12(10H)-ones. Amidomethylation of the parent anilines is also described. 
