N-bromobutanimide → HCID 15703643, compound

Participants

Reaction Steps

A solution of ethyl 2-ethoxycarbonylamino-6-methylbenzoate (10 mmol, 2.513 g.), N-bromosuccinimide (11 mmol, 1.957 g.), and catalytic amount (100 mg) of AIBN (2,2'-azobisisobutyronitrile) in 50 ml carbon tetrachloride was refluxed for 2 hours. The insoluble succinimide was removed by filtration. The filtrate was washed with saturated NaHCO3 solution (25 ml), water (30 ml), dried over MgSO4, and filtered. The filtrate was evaporated to dryness and trituated with petroleum ether to afford 2.44 g (74%) of ethyl 2-ethoxycarbonylamino-6-bromomethylbenzoate (6) as a pale yellow powder; mp 70°-72° C. IR (KBr) νmax 1740, 1685 cm-1.

Provenance & Evidence