Sodium hydride → HCID 69690118, compound

Participants

Reaction Steps

One-hundred milligrams of sodium hydride (60% water-in-oil suspension) were added to a solution of 247 mg of ethyl 3-butyrylamino-4-nitrobenzoate in 10 ml of N,N-dimethylformamide in a nitrogen atmosphere at room temperature in some divided portions. The reaction suspension was stirred at the same temperature for 1 hour, and a solution of 244 mg of 2-bromobenzyl bromide in 2 ml of N,N-dimethylformamide was gradually added dropwise thereto over a period of 10 minutes. The reaction mixture was stirred at room temperature for 1 hour, and was poured in ice water. The oily substance precipitated was extracted with methylene chloride. The organic solvent layer was washed with water, dried, and then concentrated under reduced pressure. The residue was developed through silica-gel flash column chromatography, and was eluted with a mixture of 25% ethyl acetate and n-hexane to give 540 mg of yellow oil of ethyl 3-[N-(2-bromobenzyl)butyrylamino-4-nitrobenzoate.

Provenance & Evidence