Methyl iodide → 6-Iodo-2-(methylthio)benzo[d]thiazole

Participants

Reaction Steps

To a stirred mixture of 6-iodobenzo[d]thiazole-2-thiol (0.5 g, 1.7 mmol) and potassium carbonate (0.23 g, 1.7 mmol) in THF (10 mL) was added methyl iodide (0.12 mL, 1.1 mmol). After stirring at rt overnight, the mixture was concentrated under reduced pressure to give a solid. The solid was partitioned between saturated aq sodium carbonate and DCM. The organic layer was dried over Na2SO4 and filtered, and concentrated under reduced pressure to give 6-iodo-2-(methylthio)benzo[d]thiazole as a off-white solid (0.4 g, 76%). 1H NMR (300 MHz, CDCl3) δ 8.07 (d, J=1.2 Hz, 1H), 7.69 (dd, J=1.8, 8.4 Hz, 1H), 7.58 (d, J=8.4 Hz, 1H), 2.78 (s, 3H). LCMS (ESI) m/z 308 (M+H)+.

Provenance & Evidence