Water → N-(2-Methoxyphenyl)-4-methylbenzenesulfonamide

HRID 2407

Reaktionsgleichung

Reaktionsgleichung von HRID 2407
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.N1C=CC=CC=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.O>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][S:22]([C:19]1[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=1)(=[O:24])=[O:23]

Komponenten

7

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 70002-MethoxyanilineHCID 73974-Toluenesulfonyl chloride

Produkt 1

HCID 241731N-(2-Methoxyphenyl)-4-methylbenzenesulfonamideAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. additionwere subsequently added
  2. temperaturewith cooling in an ice bath
  3. customthe resulting reaction solution
  4. extractionextracted with ethyl acetate
  5. washwashed with water, 10% sodium hydroxide aqueous solution, 1N hydrochloric acid, water and saturated brine in that order
  6. dry with materialAfter drying on anhydrous magnesium sulfate
  7. customremoving the solvent
  8. customby evaporation
  9. dissolutionthe resulting orange solid was dissolved in ethyl acetate (50 ml)
  10. washeluted with ether
  11. customsubjected to evaporation
  12. customto remove the solvent
  13. washThe resulting colorless solid which was then washed with an ether-hexane (1:1) mixture solution

Quellen und Nachweise

ORD-Eintrag
ord-04e2e891f8e24233803e97b3a1a02cf4
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728835

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