Reaction #1810845

Reaction equation

Sodium hydride

N-t-butyl-4-iodobenzenesulphonamide

1-bromo-2-methoxyethane

sodium iodide

1-bromo-2-methoxyethane

sodium iodide

→

title compound

Yield 25.2%

N-(2-Methoxyethyl)-N-(t-butyl)-4-iodobenzenesulphonamide

Yield 25.2%

Solvents

DMF

DMF

DMF

Conditions

Workup

1. 1
   Temperaturewas maintained at 0° C.
2. 2
   workup.STIRRINGthe mixture then stirred for 10 minutes
3. 3
   Temperatureto warm to ambient temperature
4. 4
   Temperatureheated at 60° C. for 20 hours
5. 5
   Temperatureto cool to ambient temperature
6. 6
   Temperaturethe reaction mixture was heated at 60° C. for a further 20 hours
7. 7
   TemperatureThe mixture was then cooled
8. 8
   Othersolvent removed by evaporation
9. 9
   workup.DISSOLUTIONThe residue was dissolved in ether (25 ml)
10. 10
    Washwashed with 10% aqueous sodium hydroxide solution (20 ml), water (3×25 ml)
11. 11
    Otherdried
12. 12
    OtherThe volatiles were removed by evaporation
13. 13
    Otherthe residue purified by flash chromatography on silica gel eluting with DCM

Procedure

Sodium hydride (71 mg, 1.77 mg) was added to a solution of N-t-butyl-4-iodobenzenesulphonamide (Method 73; 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) (which had been pre-stirred at ambient temperature for 1 hour), was then added dropwise to the mixture so that the reaction temperature was maintained at 0° C. and the mixture then stirred for 10 minutes. The mixture was allowed to warm to ambient temperature, and then heated at 60° C. for 20 hours and then allowed to cool to ambient temperature. 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 hour), was then added dropwise and the reaction mixture was heated at 60° C. for a further 20 hours. The mixture was then 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 compound (147 mg, 25%), as a clear oil that crystallised on standing. NMR: 1.23 (s, 9H), 3.24 (s, 3H), 3.48 (s, 4H), 7.57 (d, 2H), 7.94 (d, 2H).

Source