Diisopropylethylamine → 4-cyano-benzoic acid N'-[2-(3-iodo-phenyl)-acetyl]-hydrazide

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Reaction Steps

Add 1,1-carbonyldimidazole (0.72 g, 4.40 mmol) to a solution of 3-iodo-phenylacetic acid (1.20 g, 4.6 mmol) in 40 mL of N,N-dimethylacetamide, followed by N,N-diisopropylethylamine (0.79 mL, 4.40 mmol). Stir the mixture at room temperature for 2 h, add 4-cyano-benzoic acid hydrazide (0.64 g (4.0 mmol) and heat the mixture to 60° C. for 2 h. Cool the mixture to room temperature and dilute with H2O causing a solid to precipitate from solution. Collect the precipitate by filtration, wash with H2O and diethyl ether dry. Collect any further material that may crystallize from the filtrate. Extract the filtrate with CH2Cl2 and concentrate the combined organic phase provide a clear liquid. Dilute this mixture with H2O resulting in a third crop of material to precipitate from solution. Collect and combine all solid material to give 1.31 g, 71% yield of 4-cyano-benzoic acid N′-[2-(3-iodo-phenyl)-acetyl]-hydrazide as a powder.

Provenance & Evidence