Sodium Sulfite → 6-Benzothiazolecarboxaldehyde, 2-(methylthio)-

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of (2-(methylthio)benzo[d]thiazol-6-yl)methanol (958 mg, 4.5 mmol) from Step 3 of Example 36 in CH2Cl2 (20 mL) at 0° C. under argon was added Dess-Martin periodinane (2.1 g, 5.0 mmol) in small portions. After the mixture was stirred for 1 hr at 0° C., it was diluted with CH2Cl2 (100 mL) followed by the addition of a 1:1 mixture of saturated aq Na2SO3 and saturated aq NaHCO3 (40 mL). The mixture was stirred for 10 min. The layers were separated and the CH2Cl2 layer was sequentially washed with saturated aq NaHCO3 (50 mL) and brine (50 mL). The organic layer was separated and dried over Na2SO4, filtered, and concentrated under reduced pressure to yield 2-(methylthio)benzo[d]thiazole-6-carbaldehyde (937 mg, 99%) as an off white solid which did not require further purification. 1H NMR (300 MHz, DMSO-d6) δ 10.06 (s, 1H), 8.62 (s, 1H), 7.99 (s, 2H), 2.84 (s, 3H); LCMS (ESI) m/z 210 (M+H)+.

Provenance & Evidence