Sodium hydride → HCID 86758357, compound

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Reaction Steps

Sodium hydride (14.1 mmol, 0.56 g, 60% mineral oil) is dissolved in dimethylacetamide (10 ml). 1-(3,4,5-trimethoxybenzyl)-3-hydrobenzimidazol-2-one (9.1 mmol, 2.86 g) (example 10) in dimethylacetamide (10 ml) is added dropwise to the ice cooled solution which is stirred for 1 hour. Ethyl 3-bromopropionate (14.1 mmol, 1.79 ml, 2.53 g) in dimethyl-acetamide (5 ml) is added, and the mixture is stirred 24 hours at room temperature. The solution is added dropwise into ice (300 g), and the precipitate is filtered off, added to a 1:1 dichloromethane/water mixture and is extracted with dichloromethane (3×20 ml). The combined organic layers are dried with MgSO4, filtered and evaporated. Recrystallisation from ethyl acetate (5 ml) yields the title compound (R1=(CH2)2—C(O)—OEt, R2=3,4,5-trimethoxybenzyl, x=2, n=0).

Provenance & Evidence