3-(2-aminophenyl)-4-methyl-1,3-thiazole-2(3H)-thione as an ecofriendly sulphur transfer agent to prepare alkanethiols in high yield and high purity.
A new process is described for preparing very pure linear alkanethiols and linear alpha,omega-alkanedithiols using a sequential alkylation of the title compound, followed by a ring closure to quantitatively give the corresponding 3-methyl[1,3]thiazolo[3,2-a]-[3,1]benzimidazol-9-ium salt and the alkanethiol derivative under mild conditions. The alkanethiol and the heteroaromatic salt are easily separated by a simple extraction process. The intermediate thiazolium quaternary salts resulting from the first reaction step can be isolated in quantitative yields, affording an odourless protected form of the thiols.
Mehdid
Mohammed Amine
MA
Département de Chimie, Faculté de Sciences, Université d'Oran-es-Senia, Algeria. mmehdid@yahoo.fr
Djafri
Ayada
A
Roussel
Christian
C
Andreoli
Federico
F
D015394:Molecular Structure; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry*; D053778:Thiazolidines / Q000138:chemical synthesis / Q000737:chemistry; D014050:Toluene / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry
D013438:Sulfhydryl Compounds; D053778:Thiazolidines; D014050:Toluene; C033089:thiazoline-2-thione; D013455:Sulfur; C004848:dithiol