1,1'-Carbonyldiimidazole → 2-Phenyl-ethenesulfonic acid 4-chloro-2-methoxy-benzoylamide

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Reaction Steps

A mixture of 4-chloro-2-methoxybenzoic acid (509 mg, 2.7 mmol) and CDI (443 mg, 2.7 mmol) in dichloromethane (25 ml) was heated to reflux for 30 minutes. After cooling down to room temperature 2-phenyl-ethenesulfonic acid amide (for preparation see example 1-1, steps i) and ii)) (500 mg, 2.7 mmol) and DBU (416 mg, 2.7 mmol) were added and the mixture was stirred at room temperature overnight. After washing twice with 1N HCl (50 ml each) and water (50 ml) the mixture was dried over Na2SO4 and concentrated in vacuo. Preparative HPLC (RP18, methanol-water-gradient) returned the title compound (570 mg, 60% yield) as a white solid.

Provenance & Evidence