Cyclohexanecarboxamide → Cyclohexanecarbothioamide

Participants

Reaction Conditions

Reaction Steps

25.0 g Cyclohexanecarboxamide were dissolved in 200 ml toluene. 8.74 g phosphorus pentasulfide were added, followed by the addition of 33.0 g sodium bicarbonate. The reaction mixture was warmed to 115° C. and stirred overnight. The reaction mixture was filtered over a celite pad, washed with dichloromethane. The filtrate evaporated under reduced pressure. The residue was dissolved in 250 ml dichloromethane and the organic layer was washed three times with 100 ml water and twice with 100 ml brine. The aqueous layer was extracted five times with 100 ml dichloromethane. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure. The resulting residue was purified by chromatography with the eluent dichloromethane:ethyl acetate=1:1 to obtain 7.92 g Cyclohexanecarbothioic acid amide as a yellow solid.

Provenance & Evidence