Methyl iodide → Methyl 2-acetamidoethyldithiocarbamate

Participants

Reaction Steps

To a solution of 20.4 g (0.20 mol) of N-(2-aminoethyl)acetamide in 200 ml of 95% ethanol was added 27.9 ml (0.20 mol) of triethylamine and 12.0 ml (0.20 mol) of carbon disulfide. The exothermic reaction reached reflux and then cooled to ambient temperature over a 1.5 hour period. Methyl iodide (28.4 g, 0.20 mol) was then added which again produced an exothermic reaction. After an additional 1.75 hours the reaction mixture was evaporated to dryness and the solid residue was dissolved in 200 ml of water. The aqueous solution was extracted twice with 250 ml portions of ethyl acetate. The extracts were combined, shaken with solid sodium thiosulfate, dried (MgSO4) and evaporated to dryness to give methyl 2-acetamidoethyldithiocarbamate.

Provenance & Evidence