
TY  - JOUR
A1  - Badami, NV 
A1  - Cremlyn, RJW 
A1  - Swinbourne, FJ 
T1  - Chlorosulphonation of Some N-Phenyl-N'-pyridylureas
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1977
VL  - 30
IS  - 8
SP  - 1793
EP  - 1797
KW  - 
UR  - https://doi.org/10.1071/CH9771793 
N2  - 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). 
ER  -

