Sodium Hydroxide → 3-[(4-chlorophenyl)methyl]-2-(1,1-dimethylethyl)-3,5,6,7-tetrahydro-4H-benzimidazol-4-one

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Reaction Steps

To a stirred suspension of Intermediate 52 (325 mg), 1-(bromomethyl)-4-chlorobenzene (417 mg) and tetrabutylammonium bromide (272 mg) in toluene (8 mL) at ambient temperature was added aqueous sodium hydroxide 20% wt (3.25 mL). The reaction was stirred at ambient temperature for 2.5 hr. The reaction was quenched with water (20 mL) and extracted with ethyl acetate (2×20 mL). The combined organics were dried (hydrophobic frit) and concentrated in vacuo. The sample was loaded in dichloromethane and purified on silica using a 0-100% ethyl acetate-cyclohexane gradient. The appropriate fractions were combined and evaporated in vacuo to give the title compound. (126 mg). LC/MS MH+ 317, Rt 2.10 mins (5 min run).

Provenance & Evidence