Triethylamine → 4-Cyano-N-(2-furan-2-ylphenyl)-3-methylbenzamide

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Reaction Steps

To a solution of 4-cyano-3-methylbenzoic acid from Example C (187 mg, 1.16 mmol) in toluene (10 ml) was added thionyl chloride (425 μl, 5.8 mmol). The mixture was heated at reflux for 2 h, cooled, evaporated in vacuo and azeotroped with toluene. The residue was taken up in CH2Cl2 (5.0 ml) and added to a solution of 2-furan-2-yl-phenylamine from Example 21A (185 mg, 1.16 mmol) and triethylamine (324 μl, 2.32 mmol) in CH2Cl2 (5.0 ml). The mixture was stirred for 18 h, partitioned between water and chloroform and separated. The organic layers were dried and evaporated in vacuo. The residue was purified by flash chromatography on silica (eluant pet. ether:EtOAc 80:20) to give a yellow solid; yellow solid 233 mg, 66%.

Provenance & Evidence