Sodium Iodide → HCID 19025822, compound

Participants

Reaction Conditions

Reaction Steps

Part A. Sodium hydride (0.11 g of 50% mineral oil suspension, 4.64 mmol) was washed with hexane, and dried under vacuum, then suspended in dimethylsulfoxide and cooled to 0° C. A solution of 2-methyl-1H-benzimidazole (0.61 g, 4.64 mmol) in dimethylsulfoxide (5 mL) was added dropwise. The ice bath was removed, and the mixture was allowed to stir for 5 hours. A solution of bis(3-bromopropyl)sulfide (Example 366, Part A; 2.56 g, 9.27 mmol) in dimethylsulfoxide (5 mL), along with sodium iodide (0.35 g, 2.32 mmol), were added, and the resulting mixture was heated to 80° C. for 20 hours. It was then cooled to ambient temperature, and poured into 100 mL ethyl acetate. This was washed with water (4×100 mL), and the aqueous phases were back-extracted in sequence with ethyl acetate (100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was separated by flash chromatography (1:1 ethyl acetatehexane, then ethyl acetate, then acetone) to afford 1-[3-(3-bromopropyl)thiopropyl]-2-methyl-1H-benzimidazole as an oil (0.21 g, 0.64 mmol). 1NMR (CDCl3): 7.74-7.23 (4H, m); 4.28 (2H, t, J=6 Hz); 3.52 (2H, t, J=6 Hz); 2.70 (2H, t, J=7 Hz); 2.66 (3H, s); 2.55 (2H, t, J=7 Hz); 2.19-2.02 (4H, m).

Provenance & Evidence