반응 #2503

반응 방정식

water

pyridine

o-Anisidine

p-toluenesulfonyl chloride

→

title compound

수율 62.0%

N-(2-Methoxyphenyl)-p-toluenesulfonamide

수율 62.0%

용매

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONwere subsequently added
2. 2
   온도with cooling in an ice bath
3. 3
   기타the resulting reaction solution
4. 4
   추출extracted with ethyl acetate
5. 5
   세척washed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order
6. 6
   건조After drying on anhydrous magnesium sulfate
7. 7
   기타removing the solvent
8. 8
   기타by evaporation
9. 9
   workup.DISSOLUTIONthe resulting orange solid was dissolved in ethyl acetate (50 ml)
10. 10
    세척eluted with ether
11. 11
    기타subjected to evaporation
12. 12
    기타to remove the solvent
13. 13
    세척The resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution

실험 절차

o-Anisidine (2.34 ml, 20 mmol) was dissolved in toluene (60 ml) to which were subsequently added, with cooling in an ice bath, pyridine (4.58 ml, 60 mmol), p-toluenesulfonyl chloride (3.89 g, 20 mmol) and a catalytically effective amount of 4-dimethylaminopyridine. After 2.5 hours of stirring at room temperature, the resulting reaction solution was mixed-with water (50 ml), extracted with ethyl acetate and then washed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order. After drying on anhydrous magnesium sulfate and removing the solvent by evaporation, the resulting orange solid was dissolved in ethyl acetate (50 ml), adsorbed to anhydrous magnesium sulfate (20 g), eluted with ether and then subjected to evaporation to remove the solvent. The resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution to obtain 3.44 g (62.0%) of the title compound in the form of colorless prism crystals.

출처