Reaction #2503

Reaction equation

water

pyridine

o-Anisidine

p-toluenesulfonyl chloride

→

title compound

Yield 62.0%

N-(2-Methoxyphenyl)-p-toluenesulfonamide

Yield 62.0%

Solvents

toluene

Conditions

Workup

1. 1
   workup.ADDITIONwere subsequently added
2. 2
   Temperaturewith cooling in an ice bath
3. 3
   Otherthe resulting reaction solution
4. 4
   Extractionextracted with ethyl acetate
5. 5
   Washwashed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order
6. 6
   DryingAfter drying on anhydrous magnesium sulfate
7. 7
   Otherremoving the solvent
8. 8
   Otherby evaporation
9. 9
   workup.DISSOLUTIONthe resulting orange solid was dissolved in ethyl acetate (50 ml)
10. 10
    Washeluted with ether
11. 11
    Othersubjected to evaporation
12. 12
    Otherto remove the solvent
13. 13
    WashThe resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution

Procedure

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