Water → 5-Isothiocyanato-3-methylpicolinonitrile

Participants

Reaction Steps

Thiophosgene (0.24 mL, 3.1 mmol) was added to a stirred biphasic solution of 5-amino-3-methylpicolinonitrile (Intermediate 2, 275 mg, 2.07 mmol) in CHCl3 (6 mL)/water (10 mL) and the resulting orange mixture was stirred at room temperature overnight. The two layers were separated and the aqueous layer was extracted with DCM (3×). The organics were combined, washed with a saturated solution of sodium bicarbonate (2×), dried over sodium sulfate, and evaporated to dryness to afford 300 mg of 5-isothiocyanato-3-methylpicolinonitrile as an orange solid. 1H NMR (300 MHz, DMSO-d6) δ 8.66 (s, 1H), 8.06 (s, 1H), 2.5 (s, 3H).

Provenance & Evidence