par Rouchaud, Jean;Metsue, Marc;Gustin, Fabrice;Moulart, Claude;Hérin, Marc 
Référence Bulletin des Sociétés chimiques belges, 98, 5, page (319-325)
Publication Publié, 1989
Référence Bulletin des Sociétés chimiques belges, 98, 5, page (319-325)
Publication Publié, 1989
Article révisé par les pairs
| Résumé : | 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‐1‐ylmethyl)‐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 N‐amido‐acyl bond, the hydrolysis products condensing simultaneously together to give the unexpected compound 4. Copyright © 1989 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim |
