Benzo-1,3-dioxole-5-acetic acid → [2-[(E)-[[2-(1,3-benzodioxol-5-yl)acetyl]hydrazono]methyl]phenyl] 4-(trifluoromethyl)benzenesulfonate

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Reaction Steps

A solution of 2-[hydrazonomethyl]phenyl 4-(trifluoromethyl)benzenesulfonate (150 mg, 0.44 mmol) and 1,3-benzodioxol-5-ylacetic acid (1.2 equiv) in DMF (1 mL) is treated with a solution of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) (167 mg, 0.87 mmol) and 4-dimethylaminopyridine (DMAP) (106 mg, 0.87 mmol) in CH2Cl2 (10 mL). The solution is shaken overnight on an orbital shaker. The solution is evaporated to dryness using a speed. Water is added to the mixture, which is then sonicated to give a solid. The solid is filtered and washed with a large amount of water. A small amount of methanol is added and the mixture sonicated. The resulting solid is filtered and washed with more methanol to yield pure 2-((E)-{2-[2-(1,3-benzodioxol-5-yl)acetyl]hydrazono}methyl)phenyl 4-(trifluoromethyl)benzenesulfonate. The yield is 169 mg, 77%. 1H NMR (400 MHz, DMSO) □ 11.48 (2s, 1H), 8.01 (m, 6H), 7.12 (m, 6H), 5.99 (2s, 2H), 3.62 (2s, 2H). ESI− for C23H17F3N2O6S, m/z 505, (M−H)−.

Provenance & Evidence