
%0 Journal Article
%A Badami, NV 
%A Cremlyn, RJW 
%A Swinbourne, FJ 
%T Chlorosulphonation of Some N-Phenyl-N'-pyridylureas
%J Australian Journal of Chemistry
%D 1977/08/01
%V 30
%N 8
%P 1793-1797
%K 
%R https://doi.org/10.1071/CH9771793
%U https://www.publish.csiro.au/paper/CH9771793 
%X Chlorosulphonation of N-phenyl-N?-2-pyridylurea (1; X = O) and the corresponding thiourea (1 ; X = S) gave the 2?,4?-disulphonyl chloride (2; X = O, Y = Z = SO2Cl) and the 4?-sulphonyl chloride (2; X = S, Z = H, Y = SO2Cl) respectively. The sulphonyl chlorides were converted into the corresponding hydrazides, hydrazones and azides. The additional ortho-sulphonation occurring with the urea (1; X = O) is explained in terms of neighbouring group participation, and dichlorosulphonation was confirmed by the N.M.R. spectrum of the acetone disulphonohydrazone (3). In agreement with this theory, chlorosulphonation of N-phenyl-N?- 4-pyridylurea (6) gave the 4?-sulphonyl chloride (7). 
