Sodium Iodide → HCID 66987547, compound

Participants

Reaction Steps

A solution of 1-(2-hydroxyethyl)-1H-benzimidazole-5-carboxylic acid methyl ester (0.5 g. 2.27 mmol) in a mixture of dry THF:DME (25 mL:15 mL) was cooled to 5° C. NaH (0.081 g, 3.4 mmol) was added and stirred for 30 min at the same temperature. A mixture of chloromethyl methyl sulphide (0.285 g, 2.95 mmol) and NaI (0.408 g, 2.95 mmol) was then added slowly followed by TBAI (0.087 g, 0.22 mmol). The reaction was allowed to stir for overnight at ambient temperature. It was then quenched with saturated ammonium chloride solution and extracted with EtOAc. The organic layer was evaporated to give 0.53 g (83%) of 1-(2-methylsulfanylmethoxyethyl)-1H-benzimidazole-5-carboxylic acid methyl ester. 1H NMR (300 MHz, CDCl3) δ 1.9 (s, 3H), 3.9 (t, 2H), 3.95 (s, 3H), 4.4 (t, 2H), 4.6 (s, 2H), 7.45 (d, 1H), 8.05 (m, 2H), 8.5 (d, 1H)

Provenance & Evidence