Preparation of N,N-Dimethyl-N′-Arylureas
Using S,S-Dimethyl
Dithio­carbonate as a Carbonylating Reagent

Iacopo Degani; Rita Fochi; Claudio Magistris; Mara Migliaccio

doi:10.1055/s-0028-1083340

PAPER

Preparation of N,N-Dimethyl-N′-Arylureas Using S,S-Dimethyl Dithiocarbonate as a Carbonylating Reagent

Iacopo Degani, Rita Fochi*, Claudio Magistris, Mara Migliaccio
Dipartimento di Chimica Generale e Chimica Organica, Università degli Studi di Torino, C.so M. D’Azeglio 48, 10125 Torino, Italy
e-Mail: rita.fochi@unito.it;

Abstract

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Abstract

A new, general method for the preparation of N,N-dimethyl-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-dimethyl dithiocarbonate with dimethylamine to give S-methyl N,N-dimethylthiocarbamate; (2) halogenation with various halogenating reagents (chlorine, methanesulfenyl chloride, bromine, and methanesulfenyl 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.

Key words

ureas - S,S-dimethyl dithiocarbonate - halodemethylthiolations - halogenations - carbonylations

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References

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Preparation of N,N-Dimethyl-N′-Arylureas Using S,S-Dimethyl Dithio­carbonate as a Carbonylating Reagent

Preparation of N,N-Dimethyl-N′-Arylureas Using S,S-Dimethyl Dithiocarbonate as a Carbonylating Reagent