Sulphonohydrazides and related compounds. Part XI. Some substituted aryl ether sulphonhydrazides

Abstract

In a search for new pest control agents, the following benzenesulphonohydrazides have been prepared : 5-chloro-2-methoxy-, 3-chloro-4-methoxy-, 2-chloro-4-methoxy, 3-bromo-4-methoxy-, 5-bromo-Z-methoxy-, 2-bromo-4-methoxy-, 4-methoxy-3-nitro-, 3,4-dimethoxy-, 2,5-dimethoxy-, 2,4-dimethoxy-, 3-acetamido-4-methoxy-, and 5-acetamido-2-methoxy-. In addition, 4-N-sulhonylhdydrazinophenylacetic acid, and 4-N-sulphonyl hydrazino-2-methoxyphenoxyacetic acid have been prepared. The hydrazides have been converted into a number of derivatives (e.g. hydrazones, azides).THE chlorosulphonation of orthoand para-substituted anisoles, (I) and (11), went in high yield; the former reaction generally required only mild conditions (e.g. a few minutes at 0'). The ease of reaction is probably due to the lack of steric hindrance in the position para t Part X, R.

Repaglinide and Related Hypoglycemic Benzoic Acid Derivatives

“…4-[2-[[1-[2-(1-Piperidinyl)phenyl]ethyl]amino]-2-oxoethyl]-benzene-sulfonamide (49) , 15%, was obtained from 12d with 4-(carboxy-methyl)-benzene-sulfonamide (mp 176−180 °C; lit . mp 176−178 °C) and purification by column chromatography with toluene/acetone (2:1).…”

“…(d) Replacement of the amido spacer -NH-COin 6e (Table 9) by the inversed amido spacer -CO-NH-(51) led to diminished activity; for the -NH-SO 2spacer (52), no activity was detected at 25 mg/kg.…”

“…15%, was obtained from 12d with 4-(carboxy-methyl)-benzene-sulfonamide (mp 176-180 °C; lit 52. mp 176-178 °C) and purification by column chromatography with toluene/acetone (2:1).…”