Some reactions of Quinoline-8- and Ureidobenzene-sulphonyl chlorides

Quinoline-8-sulphonyl chloride (1) with hydrazine, phenylhydrazine and sodium azide gave the corresponding hydrazide (3); phenylhydrazide (4); and azide (12). The hydrazide (3) undergoes facile hydrolysis, in contrast to the rather inert sulphonyl azide (12). Chlorosulphonation of m- and p-chlorophenylureas was unsuccessful. However, the N,N-di-methylurea (18) reacted with chlorosulphonic acid to give p-(N,N-dimethy1ureido)benzenesulphonyl chloride (19), which has been converted into the hydrazide (21) and the azide (20). Both 3- methyl-4-ureidobenzenesulphonyl azide (25) and the azide (20) failed to add to norbornene, although they did react with triphenylphosphine.