Diisopropylethylamine → 5-(4-Cyano-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester

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Reaction Steps

A solution of 5-fluoro-2-nitro-4-trifluoromethyl-benzoic acid methyl ester (3.2 g, 11.98 mmol), 1H-imidazole-4-carbonitrile (2.017 g, 14.37 mmol) and ethyl-diisopropyl-amine (8.4 ml, 47.9 mmol) in 10 ml of dioxane is heated to reflux for 24 hours. The solution is allowed to cool to room temperature and evaporated. The residue is chromatographed on silica gel using gradients of dichloromethane and methanol to give 0.36 g (1.05 mmol, 8.8%) of amorphous 5-(4-cyano-imidazol-1-yl)-2-nitro-4-trifluoromethyl-benzoic acid methyl ester, ES-MS: m/z 341 [M+H]+.

Provenance & Evidence