Sodium hydride → HCID 19087704, compound

Participants

Reaction Steps

To a stirred solution of methyl 2-ethoxycarbonylamino-4-nitrobenzoate (4.00 g) in dry dimethylformamide (40 ml) was added sodium hydride (715 mg, 60% oil suspension) in several portions on an ice-bath. After stirring for 1 hour, 1-bromo-4-chlorobutane (2.81 g) was added thereto, and the resulted mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into ice-water, and extracted with ethyl acetate. The extract was washed in turn with water and brine, dried over magnesium sulfate, and evaporated. The residue was chromatographed on silica gel (180 g). Elution with a mixed solvent of hexane and ethyl acetate (3:1 V/V) gave methyl 2-[N-(4-chlorobutyl)-N-ethoxycarbonylamino]-4-nitrobenzoate (2.30 g) as an oil.

Provenance & Evidence