Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 57639715, compound

Participants

Reaction Conditions

Reaction Steps

1-(3-Hydroxyphenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide (5.0 g, 14.5 mmol), tetrabutylammonium iodide (536 mg, 1.5 mmol) and sodium hydroxide (9.8 g, 41.7 mmol) were dissolved in anhydrous ethanol and heated to reflux for 15 min. 2-Chloroethyl tosylate (581 mg, 41.67 mmol, 7.6 mL) was then added and the mixture allowed to stir at 80° C. for 18 h. After this time, the reaction mixture was concentrated in vacuo and the crude product purified by chromatography over silica gel eluting with 50% ethyl acetate/hexanes to 10% methanol in ethyl acetate to give 1-[3-(2-chloroethoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide.

Provenance & Evidence