Urea → HCID 53861673, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (0.29 g of a 60% suspension in mineral oil, 7.28 mmol) in dimethylformamide (45 ml) at ambient temperature was added a dimethylformamide solution (5 ml) of N-(3-cyanophenyl)-N′-((4-cyanophenyl)methyl)urea (0.67 g, 2.43 mmol). This mixture was stirred for 30 min before 1,4-dibromobutane (1.05 g, 4.85 mmol) in dimethylformamide (10 ml) was added over 20 min. The reaction was then heated at 70° C. for 1 h, after which analysis by thin layer chromatography (1:2 hexane:ethyl acetate) demonstrated that all of the starting urea had been consumed. The cooled reaction mixture was poured into ice water and extracted with ethyl acetate (3×). The extract was washed with 1N HCl and brine, then dried (Na2SO4) and evaporated. The crude product was purified by flash chromatography on a column of silica gel with 1:1 hexane:ethyl acetate as the eluent. There was obtained 0.47 g of pure N-(3-cyanophenyl)-N′-((4-cyanophenyl)methyl)cycloheptyl-urea; LRMS: (M+H)+ m/z 331.

Provenance & Evidence