Reacción #2543

Ecuación de reacción

triethylamine

ethyl chloroformate

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

sodium borohydride

hydrochloric acid

→

title compound

Rendimiento 69.6%

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

Rendimiento 69.6%

Disolventes

THF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaIn an atmosphere of argon and with cooling in an ice bath
2. 2
   Otrothe thus formed precipitate was removed by filtration
3. 3
   Concentraciónthe resulting filtrate was concentrated
4. 4
   workup.DISSOLUTIONThe thus obtained residue was dissolved in 5 ml of THF
5. 5
   Temperaturawith cooling in an ice bath
6. 6
   workup.STIRRINGAfter 40 minutes of stirring at the same temperature
7. 7
   Extracciónextracted with ether
8. 8
   LavadoThe organic layer was washed with saturated brine
9. 9
   Secadodried on anhydrous magnesium sulfate
10. 10
    OtroAfter removing the solvent
11. 11
    Otroby evaporation
12. 12
    Otrothe resulting colorless oily material was purified by silica gel column chromatography (ether)

Procedimiento

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.

Fuente