N-Halogen Compounds of Cyanamide Derivatives. VI. The Preparation and Reaction of 2-Carbonimidoyl-3-imino-Δ4-1,2,4-thiadiazolines
- 1 November 1976
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 49 (11) , 3165-3169
- https://doi.org/10.1246/bcsj.49.3165
Abstract
The reactions of potassium methyl cyanoiminodithiocarbonate (I), potassium methoxy and ethoxythiocarbonylcyanamide (IIa and IIb) with N-chloroamidines in various solvents were investigated. Δ4,2,4-Thiadiazolines (TDZ), IIIa–d, were obtained from I in good yields, whereas the 1,3,5-triazines obtained as by-products in addition to TDZ were formed from II and N-chlorobenzamidine (NCB) in chloroform and dichloromethane. In the latter reaction, desulfrization occurred completely to give 1,3,5-triazine and/or a chain intermediate to 1,3,5-triazine in dipolar solvents. The TDZ were readily cleft at the N–S link by hydrogen sulfide and recyclized to 1,3,5-triazines. By alkaline hydrolysis, the TDZ were transformed to 2-amino-1,3,5-triazin-4-ols.This publication has 5 references indexed in Scilit:
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