Ammonia → HCID 58513608, compound

Participants

Reaction Steps

To a solution of 4-bromo-N1-(cyclopropylmethyl)benzene-1,2-diamine (Step B, 1.48 g, 6.15 mmol) in ethyl acetate (30 mL) was added tert-butylacetyl chloride (940 μL, 6.77 mmol) at room temperature. After stirring for 1 h, p-toluenesulfonic acid monohydrate (1.29 g, 6.77 mmol) was added and the mixture was stirred under reflux for 9 h. Water (20 mL) and aqueous ammonia (10 mL) were added and the mixture was extracted with ethyl acetate (30 mL×2) and washed with brine (10 mL). The organic extracts were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1 as eluent) to give 5-bromo-1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazole (965 mg, 49%) as a brown oil and N-{5-Bromo-2-[(cyclopropylmethyl)amino]phenyl}-3,3-dimethylbutanamide (761 mg, 36%) as a white solid.

Provenance & Evidence