Triethylamine → 6-chloro-1H-imidazo[4,5-c]pyridine-2(3H)-thione

Participants

Reaction Steps

A stirred mixture of 6-chloropyridine-3,4-diamine (500 mg, 3.48 mmol), 1,1′-thiocarbonyldiimidazole (1.24 g, 6.97 mmol), and triethylamine (0.49 mL, 3.48 mmol) in anhydrous DMF (15.0 mL) was microwaved in a Biotage Initiator at 100° C. at normal power for 1 h. Then the reaction mixture was evaporated at reduced pressure, and the resulting residue extracted with DCM (200 mL) and allowed to stand at 10° C. overnight. The mixture filtered and the solids washed with cold DCM (2×20 mL), and air dried to afford the title compound as a solid. LC-MS: calculated for C6H4ClN3S 184.98 observed m/e: 186.07 (M+H)+ (Rt 0.62/2.0 min)

Provenance & Evidence