Réaction #2503

Équation de réaction

water

pyridine

o-Anisidine

p-toluenesulfonyl chloride

→

title compound

Rendement 62.0%

N-(2-Methoxyphenyl)-p-toluenesulfonamide

Rendement 62.0%

Solvants

toluene

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwere subsequently added
2. 2
   Températurewith cooling in an ice bath
3. 3
   Autrethe resulting reaction solution
4. 4
   Extractionextracted with ethyl acetate
5. 5
   Lavagewashed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order
6. 6
   SéchageAfter drying on anhydrous magnesium sulfate
7. 7
   Autreremoving the solvent
8. 8
   Autreby evaporation
9. 9
   workup.DISSOLUTIONthe resulting orange solid was dissolved in ethyl acetate (50 ml)
10. 10
    Lavageeluted with ether
11. 11
    Autresubjected to evaporation
12. 12
    Autreto remove the solvent
13. 13
    LavageThe resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution

Mode opératoire

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.

Source