反応 #2503

反応方程式

water

pyridine

o-Anisidine

p-toluenesulfonyl chloride

→

title compound

収率 62.0%

N-(2-Methoxyphenyl)-p-toluenesulfonamide

収率 62.0%

溶媒

toluene

反応条件

後処理

1. 1
   workup.ADDITIONwere subsequently added
2. 2
   温度with cooling in an ice bath
3. 3
   その他the resulting reaction solution
4. 4
   抽出extracted with ethyl acetate
5. 5
   洗浄washed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order
6. 6
   乾燥After drying on anhydrous magnesium sulfate
7. 7
   その他removing the solvent
8. 8
   その他by evaporation
9. 9
   workup.DISSOLUTIONthe resulting orange solid was dissolved in ethyl acetate (50 ml)
10. 10
    洗浄eluted with ether
11. 11
    その他subjected to evaporation
12. 12
    その他to remove the solvent
13. 13
    洗浄The resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution

実験手順

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.

出典