Water → Methyl 8-chloro-1-(2,4-dichloro-6-methylphenyl)-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-chloro-2-[(2,4-dichloro-6-methylphenyl)amino]-1-(2-hydroxyethyl)-1H-benzimidazole-7-carboxylate (156 mg, 0.364 mmol) and triethylamine (0.203 mL, 1.46 mmol) in tetrahydrofuran (7.2 mL) was added methanesulfonyl chloride (0.056 mL, 0.72 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 0.5 hr and at room temperature for 14 hr. Then the mixture was warmed to 45° C. and stirred at 45° C. for 10 hr. Water was added to the mixture and the mixture was extracted with ethyl acetate. Organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with a 25-70% ethyl acetate/n-hexane gradient mixture to give the title compound (99 mg, 0.24 mmol, 66%) as colorless crystals.

Provenance & Evidence