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

Participants

Reaction Steps

To a stirred suspension of Intermediate 56 (867 mg), 1-(bromomethyl)-4-chlorobenzene (1100 mg) and tetrabutylammonium bromide (784 mg) in toluene (20 mL) at ambient temperature was added aqueous sodium hydroxide 20% wt (9 mL). The reaction was stirred at ambient temperature for 2 hr. The reaction was quenched with saturated aqueous ammonium chloride (50 mL) and extracted with ethyl acetate (2×50 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 required product (0.89 g). LC/MS MH+ 303, Rt 2.02 min (5 min run).

Provenance & Evidence