Reaktion #2502

Reaktionsgleichung

sodium carbonate

pyridine

o-Anisidine

3-pyridinesulfonylchloride hydrochloride

→

title compound

Ausbeute 83.5%

N-(2-Methoxyphenyl)-3-pyridinesulfonamide

Ausbeute 83.5%

Lösungsmittel

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat room temperature
2. 2
   Sonstigethe resulting reaction solution
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   Waschenwashed with water and saturated brine
5. 5
   TrocknenAfter drying on anhydrous sodium carbonate
6. 6
   Sonstigeremoving the solvent
7. 7
   Sonstigeby evaporation
8. 8
   Sonstigethe resulting orange solid was purified by a silica gel column chromatography (ether:hexane=3:1)
9. 9
   Sonstigeto obtain a light orange solid which
10. 10
    Waschenwas subsequently washed with an ether-hexane (1:3) mixture solution

Vorschrift

o-Anisidine (377 mg, 3.0 mmol) was dissolved in toluene (10 ml) to which were subsequently added pyridine (0.48 ml, 6.0 mmol) and 3-pyridinesulfonylchloride hydrochloride (642 mg, 3.0 mmol) at room temperature. After 1.5 hours of stirring at 100° C., the resulting reaction solution was mixed with water (20 ml), adjusted to pH 7 to 8 with anhydrous sodium carbonate, extracted with ethyl acetate and then washed with water and saturated brine. After drying on anhydrous sodium carbonate and removing the solvent by evaporation, the resulting orange solid was purified by a silica gel column chromatography (ether:hexane=3:1) to obtain a light orange solid which was subsequently washed with an ether-hexane (1:3) mixture solution to obtain 662 mg (83.5%) of the title compound in the form of colorless prism crystals.

Quelle