
TY  - JOUR
A1  - O'Conner, CJ 
A1  - Ramage, RE 
T1  - Reactions of N-Aryl-4-chlorobenzamides in sulphuric acid
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1977
VL  - 30
IS  - 3
SP  - 527
EP  - 534
KW  - 
UR  - https://doi.org/10.1071/CH9770527 
N2  - Rate constants of reaction of 4-chloro-N-phenylbenzamide at 353 and 373 K, and of N-benzyl-4-chlorobenzamide at 373 K have been studied in aqueous sulphuric acid. The rate acidity profiles in <40% w/w H2SO4 show the typical bell shape normally observed for the A2 hydrolysis of amides. However, with increasing acidity there is competition from sulphonation on the N-aryl substituent and subsequent A 2 hydrolysis of the sulphonated intermediates. At >75% w/w H2SO4, sulphonated 4-chloro- N-phenylbenzamide is charred. At >52% w/w H2SO4, sulphonation of N- benzyl-4-chlorobenzamide ceases and is replaced by A 1 hydrolysis of the substrate. 
ER  -

