Carbon Disulfide → (S)-4-Phenylthiazolidine-2-thione

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-(+)-2-Phenylglycinol(1.40 g, 10 mmol) in 1N KOH/H2O (10 ml) at room temperature, was added carbon disulfide (3 ml, 50 mmol). The resulting solution was heated by a pre-heated oil-bath (110° C.) to reflux for 20 h after which the reaction mixture was cooled to room temperature and extracted with CH2Cl2 (3×30 ml), dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by column chromatography over silica gel with 1:1 hexane/CH2Cl2 followed by CH2Cl2 as the eluting system (Rf=0.09, CH2Cl2:hexane=7:3) to obtain 4(S)-phenyl-thiazolidine-2-thione (170 mg, 9%).

Provenance & Evidence