Реакция #2503

Уравнение реакции

water

pyridine

o-Anisidine

p-toluenesulfonyl chloride

→

title compound

Выход 62.0%

N-(2-Methoxyphenyl)-p-toluenesulfonamide

Выход 62.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere subsequently added
2. 2
   Температураwith cooling in an ice bath
3. 3
   Другоеthe resulting reaction solution
4. 4
   Экстракцияextracted with ethyl acetate
5. 5
   Промывкаwashed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order
6. 6
   СушкаAfter drying on anhydrous magnesium sulfate
7. 7
   Другоеremoving the solvent
8. 8
   Другоеby evaporation
9. 9
   workup.DISSOLUTIONthe resulting orange solid was dissolved in ethyl acetate (50 ml)
10. 10
    Промывкаeluted with ether
11. 11
    Другоеsubjected to evaporation
12. 12
    Другоеto remove the solvent
13. 13
    ПромывкаThe resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution

Методика

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.

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