Carbon Disulfide → Cyclohexyl isothiocyanate

Participants

Reaction Steps

Cyclohexylamine (99 mg, 0.001 mol) and 101 mg (0.001 mol) of triethylamine together with 76 mg (0.001 mol) of carbon disulfide were dissolved in 10 ml of acetonitrile to prepare a solution of cyclohexyldithiocarbamic acid triethylamine salt in acetonitrile. To this solution was added 256 mg (0.001 mol) of DSC and the admixture was stirred for 24 hours at room temperature. The reaction mixture is distilled to remove the acetonitrile and the residue was admixed with ethyl acetate, washed with 1 N-HCl, with aqueous 4% NaHCO3, with water and finally with saturated aqueous NaCl, followed by drying over anhydrous sodium sulfate. The resulting solution was distilled to remove the ethyl acetate and the residue was purified by column-chromatography on silica gel developed with hexane-benzene to give cyclohexylisothiocyanate in a yield of 85%.

Provenance & Evidence