Reaktion #2503

Reaktionsgleichung

water

pyridine

o-Anisidine

p-toluenesulfonyl chloride

→

title compound

Ausbeute 62.0%

N-(2-Methoxyphenyl)-p-toluenesulfonamide

Ausbeute 62.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere subsequently added
2. 2
   Temperaturwith cooling in an ice bath
3. 3
   Sonstigethe resulting reaction solution
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   Waschenwashed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order
6. 6
   TrocknenAfter drying on anhydrous magnesium sulfate
7. 7
   Sonstigeremoving the solvent
8. 8
   Sonstigeby evaporation
9. 9
   workup.DISSOLUTIONthe resulting orange solid was dissolved in ethyl acetate (50 ml)
10. 10
    Wascheneluted with ether
11. 11
    Sonstigesubjected to evaporation
12. 12
    Sonstigeto remove the solvent
13. 13
    WaschenThe resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution

Vorschrift

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.

Quelle