تفاعل #2503

معادلة التفاعل

water

pyridine

o-Anisidine

p-toluenesulfonyl chloride

→

title compound

المردود 62.0%

N-(2-Methoxyphenyl)-p-toluenesulfonamide

المردود 62.0%

المذيبات

toluene

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere subsequently added
2. 2
   درجة الحرارةwith cooling in an ice bath
3. 3
   أخرىthe resulting reaction solution
4. 4
   استخلاصextracted with ethyl acetate
5. 5
   غسيلwashed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order
6. 6
   تجفيفAfter drying on anhydrous magnesium sulfate
7. 7
   أخرىremoving the solvent
8. 8
   أخرىby evaporation
9. 9
   workup.DISSOLUTIONthe resulting orange solid was dissolved in ethyl acetate (50 ml)
10. 10
    غسيلeluted with ether
11. 11
    أخرىsubjected to evaporation
12. 12
    أخرىto remove the solvent
13. 13
    غسيلThe resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution

الإجراء التجريبي

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.

المصدر