Sodium Iodide → HCID 19025817, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (2.24 g of 50% w/w slurry in mineral oil, 46.7 mmol) was washed in hexane and dried under vacuum. Dimethylsulfoxide (30 mL) was added, followed by a solution of 2-(2-hydroxyethyl)pyridine (5.00 mL, 44.4 mmol) in dimethylsulfoxide (20 mL) dropwise. After stirring for 2 hours, the mixture was treated with 1H-bromo-5-chloropentane (6.00 mL, 45.5 mmol), and was heated to 80° C. for 18 hours. The resulting mixture was cooled, treated with 4,5-diphenyl-2-mercapto-1H-imidazole (7.00 g, 27.7 mmol), potassium carbonate (7.00 g, 50.6 mmol) and sodium iodide (1 g), and heated again to 80° C. for an additional 24 hours. The mixture was cooled, poured into 400 mL ethyl acetate, and washed with water (4×400 mL). The ethyl acetate layer was washed with saturated aqueous sodium chloride (200 mL), dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was separated by flash chromatography, and the product was further purified by preparative thin-layer chromatography to afford the title compound as an oil (940 mg, 2.12 mmol, 8%). 1H NMR (CDCl3): 11.53 (1H, br s); 8.48 (1H, dt, J=5.1, 0.9 Hz); 7.61-7.06 (13H, m); 3.70 (2H, t, J=6.6 Hz); 3.37 (2H, t, J=6.0 Hz); 2.97 (2H, t, J=7.3 Hz); 2.94 (2H, t, J=6.6 Hz); 1.68-1.30 (6H, m). High-resolution mass spectrum: calculated for C27H30N3OS 444.2110, observed 444.2101, difference 1.9 ppm.

Provenance & Evidence