| Popis: |
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. |
