
TY  - JOUR
A1  - Rosevear, J 
A1  - Wilshire, JFK 
T1  - A Comparison of the Reactions of Some Ethyl N-Arylcarbamates With Those of the Corresponding Acetanilides. II. Amidomethylation With N-Hydroxy-methylphthalimide
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1990
VL  - 43
IS  - 2
SP  - 339
EP  - 353
KW  - 
UR  - https://doi.org/10.1071/CH9900339 
N2  - 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. 
ER  -

