Reacción #2503

Ecuación de reacción

water

pyridine

o-Anisidine

p-toluenesulfonyl chloride

→

title compound

Rendimiento 62.0%

N-(2-Methoxyphenyl)-p-toluenesulfonamide

Rendimiento 62.0%

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere subsequently added
2. 2
   Temperaturawith cooling in an ice bath
3. 3
   Otrothe resulting reaction solution
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   Lavadowashed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order
6. 6
   SecadoAfter drying on anhydrous magnesium sulfate
7. 7
   Otroremoving the solvent
8. 8
   Otroby evaporation
9. 9
   workup.DISSOLUTIONthe resulting orange solid was dissolved in ethyl acetate (50 ml)
10. 10
    Lavadoeluted with ether
11. 11
    Otrosubjected to evaporation
12. 12
    Otroto remove the solvent
13. 13
    LavadoThe resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution

Procedimiento

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.

Fuente