Benzoyl chloride → Benzoylamidoacetonitrile

Participants

Reaction Steps

Benzoylaminoacetonitrile was synthesized in a conventional manner from benzoyl chloride and aminoacetonitrile. Bromine (40 g) was added at a time to a solution of 4.0 g of the benzoylaminoacetonitrile in 200 ml of ethyl acetate at room temperature. When the color of bromine in the reaction solution disappeared, the reaction solution was cooled to 0° to 5° C. 2-Butyn-1-ol (2.1 g) and 5.6 g of triethylamine were dissolved in 10 ml of ethyl acetate, and the solution was added dropwise to the ethyl acetate solution previously cooled. After the addition, the reaction was continued for 30 minutes at room temperature. Triethylamine hydrobromide was separated by filtration, and the filtrate was distilled under reduced pressure to evaporate the solvent. The residue was purified by silica gel column chromatography. By elution with hexane-ethyl acetate, 3.8 g of alpha-benzoylamino-(2-butynyloxy)acetonitrile was obtained as a solid. The yield was 65.5%, and the melting point of the product was 84° to 85.5° C.

Provenance & Evidence