반응 #2543

반응 방정식

triethylamine

ethyl chloroformate

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

sodium borohydride

hydrochloric acid

→

title compound

수율 69.6%

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

수율 69.6%

용매

THF

water

반응 조건

후처리

1. 1
   온도In an atmosphere of argon and with cooling in an ice bath
2. 2
   기타the thus formed precipitate was removed by filtration
3. 3
   농축the resulting filtrate was concentrated
4. 4
   workup.DISSOLUTIONThe thus obtained residue was dissolved in 5 ml of THF
5. 5
   온도with cooling in an ice bath
6. 6
   workup.STIRRINGAfter 40 minutes of stirring at the same temperature
7. 7
   추출extracted with ether
8. 8
   세척The organic layer was washed with saturated brine
9. 9
   건조dried on anhydrous magnesium sulfate
10. 10
    기타After removing the solvent
11. 11
    기타by evaporation
12. 12
    기타the resulting colorless oily material was purified by silica gel column chromatography (ether)

실험 절차

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.

출처