Dimethyl Sulfate → 2-Methylthio-1,3-dithiolium perchlorate

Reaction equation

[S:1]1[CH:5]=[CH:4][S:3][C:2]1=[S:6].[CH3:7]OS(=O)(=O)OC.[Cl:14]([O-:18])(=[O:17])(=[O:16])=[O:15].[Na+]>>[Cl:14]([O-:18])(=[O:17])(=[O:16])=[O:15].[CH3:7][S:6][C:2]1[S:3][CH:4]=[CH:5][S+:1]=1

Participants

Reactant 3

HCID 6497Dimethyl Sulfate

HCID 702541,3-Dithiole-2-Thione

HCID 522606Sodium Perchlorate

Product 1

HCID 230390092-Methylthio-1,3-dithiolium perchlorateYield 85.8%

Procedure

A mixture comprising 26.8g (0.2 mole) of 1,3-dithiol-2-thion and 25.2g (0.2 mole) of dimethylsulfuric acid was reacted at 60° C for 30 minutes and then at 90° C for 30 minutes. After cooling, the reaction product was poured into 150 ml of a saturated aqueous sodium perchlorate solution to deposit crystals. The crystals were recovered by filtration, washed with ether, dried and then recrystallized from methanol to obtain 42.5g of yellow crystals, m.p. 42°-46° C, yield 85.8%.