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

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Reaction Steps

To Intermediate 56 (2nd alternative preparation) (5.4 g) in Toluene (120 mL) was added 1-(bromomethyl)-4-iodobenzene (9.00 g) and tetrabutylammonium bromide (4.88 g) then sodium hydroxide, 5M aq (66.7 mL). The mixture was then stirred at room temperature, stirring vigorously to mix the phases for 1.5 h. The mixture was partitioned between ethyl acetate and water. The brown solid was filtered. The 2 phases were separated and the aqueous layer extracted well with ethyl acetate. The combined organics were dried (hydrophobic frit) and evaporated. The sample was loaded in dichloromethane and purified by column chromatography (silica) using 0-100% ethyl acetate-cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the required product 6.65 g as a brown oil. LC/MS MH+ 395, Rt 2.88 min (5 min run).

Provenance & Evidence