Saccharin → 2-(1,3-Benzodioxol-5-ylmethyl)-1,1-dioxo-1,2-benzothiazol-3-one

Participants

Reaction Steps

To saccharin (5.0 g, 0.0273 mol) in DMF (10 mL) was added Nail (1.15 g, 60% in oil, 0.0288 mol) with ice bath cooling. After stirring for 10 minutes. a solution of 3,4-methylenedioxybenzyl chloride in methylene chloride, 50% by weight, (10 g, 0.0293 mol) was added and the mixture stirred for 16 hours. The mixture was diluted with ethyl acetate (200 mL) containing 10% methylene chloride and washed with IN HCl (2×100 mL). The organic phase was washed with brine and dried over MgSO4. The mixture was concentrated until crystals were apparent. After standing for 16 hours the product was collected by filtration (4.2 g, 49%);

Provenance & Evidence