15249-51-1Relevant academic research and scientific papers
Preparation of N,N-Dimethyl-N′-arylureas using S,S-dimethyl dithio-carbonate as a carbonylating reagent
Degani, Iacopo,Fochi, Rita,Magistris, Claudio,Migliaccio, Mara
experimental part, p. 801 - 808 (2009/08/07)
A new, general method for the preparation of N,N-di-methyl-N′- arylureas using S,S-dimethyl dithiocarbonate as a phosgene substitute is reported. The method has been set up according to four procedures, all including three steps: (1) reaction of S,S-di- methyl dithiocarbonate with dimethylamine to give S-methyl N,N-dimethylthiocarbamate; (2) halogenation with various halogenating reagents (chlorine, methanesulfenyl chloride, bromine, and meth-anesulfenyl bromide) to give N,N-dimethylcarbamoyl chloride or bromide; (3) in situ reaction with primary arylamines. All the target products were obtained in high yields (85-98%; 16 reactions, average yield 93%) and with high purity. Also noteworthy is the recovery of byproducts of industrial interest, namely methanethiol and dimethyl disulfide, with complete exploitation of the reagent S,S- dimethyl dithiocarbonate. Georg Thieme Verlag Stuttgart.
