Sodium hydride → 1-[6-(2,6-Dichloro-4-methylphenoxy)hexyl]-3-(3-pyridyl)-2-imidazolidinone

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Reaction Steps

To a solution of 1-(3-pyridyl)-2-imidazolidinone (0.10 g, 0.63 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 38.2 mg, 0.96 mmol). The mixture was stirred at room temperature for 30 minutes and then cooled in ice bath. 2-[(6-Bromohexyl)oxy]-1,3-dichloro-5-methylbenzene (0.22 g, 0.64 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with MeOH, and the solvents were pumped off. 5 mL of a saturated aqueous NH4Cl solution and 10 mL of dichloromethane were successively added to the residue. The dichloromethane layer was separated and dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 5) as a white solid (0.36 g, 90%).

Provenance & Evidence