Reaction #2543

Reaction equation

triethylamine

ethyl chloroformate

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

sodium borohydride

hydrochloric acid

→

title compound

Yield 69.6%

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

Yield 69.6%

Solvents

THF

water

Conditions

Workup

1. 1
   TemperatureIn an atmosphere of argon and with cooling in an ice bath
2. 2
   Otherthe thus formed precipitate was removed by filtration
3. 3
   Concentrationthe resulting filtrate was concentrated
4. 4
   workup.DISSOLUTIONThe thus obtained residue was dissolved in 5 ml of THF
5. 5
   Temperaturewith cooling in an ice bath
6. 6
   workup.STIRRINGAfter 40 minutes of stirring at the same temperature
7. 7
   Extractionextracted with ether
8. 8
   WashThe organic layer was washed with saturated brine
9. 9
   Dryingdried on anhydrous magnesium sulfate
10. 10
    OtherAfter removing the solvent
11. 11
    Otherby evaporation
12. 12
    Otherthe resulting colorless oily material was purified by silica gel column chromatography (ether)

Procedure

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.

Source