Some sulfonyl derivatives of phenoxyacetamide

Abstract

Phenoxyacetamide (2) by treatment with chlorosulfonic acid gave the 4- sulfonyl chloride (3); this was characterized by preparation of the sulfonamide (4) and the sulfonohydrazide (5). The latter compound has been converted into five hydrazones (6) by condensation with the appropriate carbonyl compounds; with acetylacetone cyclization occurred to form the 3,5-dimethylpyrazole (7). 2,4-Dichloro- and 4-chloro-2- methyl-phenoxyacetamides were chlorosulfonated to the corresponding 6- sulfonyl chlorides (8) and (10), and these were characterized as the sulfonohydrazides (9) and (11). In contrast, attempts to chlorosulfonate 2,4-dichloro- and 4-chloro-2-methyl-phenoxyacetic acids were unsuccessful, and the reasons for this failure are briefly discussed.