Chlorosulphonation of Some N-Phenyl-N'-pyridylureas
- 1 January 1977
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 30 (8) , 1793-1797
- https://doi.org/10.1071/ch9771793
Abstract
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).Keywords
This publication has 1 reference indexed in Scilit:
- Cytokinin activity of some substituted ureas and thioureasProceedings of the Royal Society of London. B. Biological Sciences, 1966