Sodium Iodide → HCID 68881545, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (71 mg, 1.77 mg), was added to a solution of N-t-butyl-4-iodobenzenesulphonamide (Method 5; 500 mg, 1.47 mmol), in anhydrous DMF (15 ml), under nitrogen at 0° C. The resulting suspension was stirred at 0° C. for 30 minutes. A solution of 1-bromo-2-methoxyethane (167 μl, 1.77 mmol), and sodium iodide (265 mg, 1.77 mmol), in DMF (15 ml), (pre-stirred at ambient temperature for 1 hr), was then added dropwise to the mixture while the, reaction temperature was maintained at 0° C. and the mixture stirred for 10 minutes. The mixture was allowed to warm to ambient temperature, and then heated at 60° C. for 20 hours. A further solution of 1-bromo-2-methoxyethane (167 μl, 1.77 mmol), and sodium iodide (265 mg, 1.77 mmol), in DMF (15 ml), (pre-stirred at ambient temperature for 1 hr), was then added dropwise to the mixture at ambient temperature and the reaction mixture was heated at 60° C. for 20 hours. The mixture was cooled and solvent removed by evaporation. The residue was dissolved in ether (25 ml), washed with 10% aqueous sodium hydroxide solution (20 ml), water (3×25 ml), and dried. The volatiles were removed by evaporation and the residue purified by flash chromatography on silica gel eluting with DCM to yield the title product as a clear oil that crystallised on standing (147 mg, 25%), NMR: 1.23 (s, 9H), 3.24 (s, 3H), 3.48 (s, 4H), 7.57 (d, 2H), 7.94 (d, 2H).

Provenance & Evidence