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

Participants

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 (2.0 g, 5.0 mmol) portionwise. The mixture was stirred for 1 h and then diluted with CH2Cl2 (100 mL). To this mixture was added a 50/50 mixture of saturated aq sodium sulfite and saturated aq sodium bicarbonate (40 mL). This mixture was stirred for 10 min and then the CH2Cl2 layer was separated, washed with a saturated aq sodium bicarbonate (50 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford 2-(methylthio)benzo[d]thiazole-6-carbaldehyde (937 mg, 99%) as a white solid. LCMS (ESI) m/z 210 (M+H)+.

Provenance & Evidence