Sodium hydride → HCID 22419172, compound

Participants

Reaction Conditions

Reaction Steps

340 mg (1.5 mmol) Of the benzimidazol-4,7-dione was dissolved in 15 ml of dimehtylformarnide, and this was cooled to 0° C. After 65 mg (1.6 mmol) of 60% sodium hydride was added and the mixture was stirred for 30 min. A solution of 503 mg (1.5 mmol) of (2'-t-butoxycarbonylbiphenyl-4-yl)methyl bromide in 2 ml of dimethylformamide was added dropwise and the mixture was stirred for 1 hour. To the reaction mixture was added an aqueous saturated solution of ammonium chloride, and this was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution, and this was dried over anhydrous sodium sulphate, and the solvent was distilled off under the reduced pressure. The resultant crude product was purified by silica gel chromatography (ethyl acetate: n-hexane=5:1) to obtain 421 mg of 1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-n-butyl-5,6-dimethyl-1H-benzimidazol-4,7-dione as yellow oily material (Yield 58%). This has the following NMR spectrum. δ ppm (CDCl3): 0.91 (3H, t, J=7 Hz), 1.21 (9H, s), 1.35-1.43 (H, s), 1.76-1.82 (2H, m), 2.04 (3H, s), 2.10 (3H, s), 5.62 (2H, s), 7.10 (2H, d, J=8 Hz), 7.27-7.30 (3H, m), 7.39-7.42 (1H, m), 7.45-7.48 (1H, m), 7.78 (1H, dd, J=6, 1 Hz)

Provenance & Evidence