Sodium Carbonate → 6-chloro-N-cyclohexyl-2-(cyclopentylthio)nicotinamide

Participants

Reaction Conditions

Reaction Steps

Cyclopentanethiol (7.84 mL, 73.22 mmol) was added in one portion to 2,6-dichloro-N-cyclohexylnicotinamide (20 g, 73.22 mmol) and sodium carbonate (23.28 g, 219.65 mmol) in DMF (150 mL). The resulting suspension was stirred at 60° C. for 3 hours. The mixture was cooled, evaporated, DCM (250 mL) was added and the mixture was washed with water (3×100 mL) and brine (50 mL), dried (MgSO4), filtered and evaporated to a sticky pale yellow solid. This was triturated with 4:1 hexane:ethyl acetate, filtered and dried to give 6-chloro-N-cyclohexyl-2-(cyclopentylthio)nicotinamide (13.8 g, 55.6%) as a white solid.

Provenance & Evidence