125709-81-1Relevant articles and documents
ACID CATALYZED HETEROLYSIS OF A PYRAZOL α-CHLOROACETANILIDE DERIVATIVE WITH ALKYL-AMIDONITROGEN FISSION
Rouchaud, Jean,Metsue, Marc,Gustin, Fabrice,Moulart, Claude,Herin, Marc
, p. 319 - 326 (2007/10/02)
The base-catalyzed hydrolysis of 2-chloro-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1-ylmethyl)-acetamide (1) generated 2-hydroxy-N-(2,6-dimethylphenyl)-N-(1H-pyrazol-1ylmethyl)-acetamide (2).The acid-catalyzed hydrolysis of compound 1 generated after a short time 2-chloro-N-(2,6-dimethyl)-acetamide (3) and pyrazol (5); after a longer period of time, 4,4'-methylenebis-(2,6-dimethylbenzenamine) (4) and pyrazol (5) were formed; compound 4 was formed by condensation of the non isolated intermediates 2,6-dimethylaniline and formaldehyde.Thus the base-catalyzed hydrolysis of compound 1 did not cleave the amide; the acid-catalyzed one first cleaved the N-amido-alkyl bond; then, the Namido-acyl bond, the hydrolysis products condensing simultaneously together to give the unexpected compound 4.