Sodium hydride → 2-Benzo[1,3]dioxol-5-ylmethyl-4-hydroxy-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester

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Reaction Steps

To 4-hydroxy-1,1-dioxo-1,2-dihydro-1λ6 -benzo[e][1,2]thiazine-3-carboxylic acid methyl ester (1.48 g, 5.84 mmol) in DMF (10 mL) was added sodium hydride (0.257 g, 60%, 6.4 mmol) and the mixture stirred for 5 minutes. 3,4-methylenedioxybenzyl chloride (2.2 g, 50 wt. % in dichloromethane, 6.4 mmol) was added and the mixture stirred at room temperature for 18 hours. Diluted with ethyl acetate (100 mL), washed with water (2×80 mL), brine (80 mL), dried over magnesium sulfate, removed solvent in vacuo, and crystallized from ethyl acetate/heptane to give the title compound (1.63 g, 72%);

Provenance & Evidence