Reaktion #2543

Reaktionsgleichung

triethylamine

ethyl chloroformate

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

sodium borohydride

hydrochloric acid

→

title compound

Ausbeute 69.6%

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

Ausbeute 69.6%

Lösungsmittel

THF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturIn an atmosphere of argon and with cooling in an ice bath
2. 2
   Sonstigethe thus formed precipitate was removed by filtration
3. 3
   Einengenthe resulting filtrate was concentrated
4. 4
   workup.DISSOLUTIONThe thus obtained residue was dissolved in 5 ml of THF
5. 5
   Temperaturwith cooling in an ice bath
6. 6
   workup.STIRRINGAfter 40 minutes of stirring at the same temperature
7. 7
   Extraktionextracted with ether
8. 8
   WaschenThe organic layer was washed with saturated brine
9. 9
   Trocknendried on anhydrous magnesium sulfate
10. 10
    SonstigeAfter removing the solvent
11. 11
    Sonstigeby evaporation
12. 12
    Sonstigethe resulting colorless oily material was purified by silica gel column chromatography (ether)

Vorschrift

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.

Quelle