5,6-Dimethylbenzimidazole → HCID 929363, compound

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Reaction Steps

In an oven dried nitrogen purged 3 neck 50 mL round bottom flask, 5.00 g (34.20 mmol) of 5,6-dimethylbenzimidazole in 20 mL of dry dimethylformamide is reacted with 1.51 g (37.62 mmol) of sodium hydride at room temperature for 4 h. 2.34 mL (37.62 mmol) of iodomethane is added and reaction is allowed to stir at room temperature overnight. Reaction is quenched with water, layers are separated, extract aqueous 3×50 mL ethyl acetate, dry (MgSO4), and concentrate. The crude mixture is purified by chromatography using dichloromethane: methanol as a solvent system. Product containing fractions are combined to obtain 3.75 g of the title compound, 68% yield. MS, ES+=161.1. H1NMR (CDCl3) δ 7.98 (s, 1H); 7.37 (s, 1H); 7.29 (s, 1H); 3.74 (s, 3H); 2.31 (s, 3H); 2.28 (s, 3H) ppm

Provenance & Evidence