反応 #2543

反応方程式

triethylamine

ethyl chloroformate

4-[(2-methoxyanilino)sulfonyl]benzoic acid

sodium borohydride

hydrochloric acid

→

title compound

収率 69.6%

4-Hydroxymethyl-N-(2-methoxyphenyl)benzenesulfonamide

収率 69.6%

溶媒

THF

water

反応条件

後処理

1. 1
   温度In an atmosphere of argon and with cooling in an ice bath
2. 2
   その他the thus formed precipitate was removed by filtration
3. 3
   濃縮the resulting filtrate was concentrated
4. 4
   workup.DISSOLUTIONThe thus obtained residue was dissolved in 5 ml of THF
5. 5
   温度with cooling in an ice bath
6. 6
   workup.STIRRINGAfter 40 minutes of stirring at the same temperature
7. 7
   抽出extracted with ether
8. 8
   洗浄The organic layer was washed with saturated brine
9. 9
   乾燥dried on anhydrous magnesium sulfate
10. 10
    その他After removing the solvent
11. 11
    その他by evaporation
12. 12
    その他the resulting colorless oily material was purified by silica gel column chromatography (ether)

実験手順

In an atmosphere of argon and with cooling in an ice bath, 4-[(2-methoxyanilino)sulfonyl]benzoic acid (150 mg, 0.488 mmol) was dissolved in THF (5 ml), to which were subsequently added dropwise triethylamine (0.14 ml, 1.0 mmol) and ethyl chloroformate (50 μl, 0.509 mmol). After 30 minutes of stirring at the same temperature, the thus formed precipitate was removed by filtration, and the resulting filtrate was concentrated. The thus obtained residue was dissolved in 5 ml of THF, and, with cooling in an ice bath, sodium borohydride (46.5 mg, 1.22 mmol) and water (1 ml) were added to the resulting solution. After 40 minutes of stirring at the same temperature, the reaction mixture was adjusted to pH 4 to 5 with 2N hydrochloric acid and extracted with ether. The organic layer was washed with saturated brine and dried on anhydrous magnesium sulfate. After removing the solvent by evaporation, the resulting colorless oily material was purified by silica gel column chromatography (ether) to obtain 99.6 mg (69.6%) of the title compound in the form of colorless solid.

出典