反应 #1810845

反应方程式

Sodium hydride

N-t-butyl-4-iodobenzenesulphonamide

1-bromo-2-methoxyethane

sodium iodide

1-bromo-2-methoxyethane

sodium iodide

→

title compound

收率 25.2%

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

收率 25.2%

溶剂

DMF

DMF

DMF

反应条件

后处理

1. 1
   温度was maintained at 0° C.
2. 2
   workup.STIRRINGthe mixture then stirred for 10 minutes
3. 3
   温度to warm to ambient temperature
4. 4
   温度heated at 60° C. for 20 hours
5. 5
   温度to cool to ambient temperature
6. 6
   温度the reaction mixture was heated at 60° C. for a further 20 hours
7. 7
   温度The mixture was then cooled
8. 8
   其他solvent removed by evaporation
9. 9
   workup.DISSOLUTIONThe residue was dissolved in ether (25 ml)
10. 10
    洗涤washed with 10% aqueous sodium hydroxide solution (20 ml), water (3×25 ml)
11. 11
    其他dried
12. 12
    其他The volatiles were removed by evaporation
13. 13
    其他the residue purified by flash chromatography on silica gel eluting with DCM

实验过程

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).

来源