Acetic Anhydride → 4-[3-Acetyl-1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile

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Reaction Steps

4-[1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (150 mg) (0.38 mmol) in acetic anhydride (5 ml) was refluxed 3 days. After cooling, the reaction mixture was poured on water and extracted with tBuOMe. The organic layer was washed with water, dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (DCM/acetone, 97.5/2.5), then HPLC to give 4-[3-Acetyl-1-(3,5-Dichlorophenyl)-2-oxo-1,2,3,4,5,6-hexahydro-benzimidazol-3a-ylmethyl]benzonitrile (13.5 mg) as a white solid. 1H NMR (CDCl3): 7.55 (2H, d), 7.3-7.2 (3H, m), 6.70 (2H, m), 4.95 (1H, m), 3.70 (1H, d), 3.05 (1H, m), 2.50 (3H, s), 2.45-2.1 (2H, m), 2.1-1.6 (3H, m).

Provenance & Evidence