A new, general method for the preparation of N,N-dimethyl-N'-arylureas using S,S-dimethyl dithiocarbonate as a phosgene substitute is reporetd. 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.

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

FOCHI, Rita;MAGISTRIS, CLAUDIO;
2009-01-01

Abstract

A new, general method for the preparation of N,N-dimethyl-N'-arylureas using S,S-dimethyl dithiocarbonate as a phosgene substitute is reporetd. 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.
2009
-
801
808
ureas; S; S-dimethyl dithiocarbonate; halodemethylthiolations; halogenations; carbonylations
Iacopo Degani; Rita Fochi; Claudio Magistris; Mara Migliaccio
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/85799
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? 6
social impact