Some substituted ureidobenzenesulphonohydrazides

Abstract

Chlorosulphonation of o-chlorophenyl and o-tolylurea afforded the corresponding 3-substituted 4-ureidobenzenesulphonyl chlorides (2). With m- and p-tolylurea low yields of sulphonyl chlorides were obtained. The m-isomer gave 2-methyl-4-ureidobenzenesulphonyl chloride, but n.m.r, studies indicated that the p-isomer afforded a mixture of mainly 2-methyl-5-ureido- and some 5-methyl-2-ureido-benzenesulphonyl chloride. The various sulphonyl chlorides have been converted intohydrazides, hydrazones and azides. 3-Methyl-4-ureidobenzenesulphonyl azide (11) undergoes pseudohalogen replacement of the azido group, on treatment with butylamine, to give the corresponding N-utylsulphonamide (12). Attempts to obtain nitrene-insertion reactions by heating the azide (11) with naphthalene andanisole were unsuccessful.