Thiophosgene → 6-Isothiocyanato-2-(trifluoromethyl)nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-amino-2-(trifluoromethyl)nicotinonitrile (648 mg, 3.5 mmol) and thiophosgene (0.4 mL, 5.2 mmol) in DCE (8 mL) was heated to 80° C. overnight. The mixture was cooled to room temperature and diluted with DCM/water. 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 521 mg of 6-isothiocyanato-2-(trifluoromethyl)nicotinonitrile (70% pure) as a brown oil. 1H NMR (300 MHz, DMSO-d6) δ 8.73 (d, 1H), 7.93 (d, 1H).

Provenance & Evidence