Reacción #2502

Ecuación de reacción

sodium carbonate

pyridine

o-Anisidine

3-pyridinesulfonylchloride hydrochloride

→

title compound

Rendimiento 83.5%

N-(2-Methoxyphenyl)-3-pyridinesulfonamide

Rendimiento 83.5%

Disolventes

water

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroat room temperature
2. 2
   Otrothe resulting reaction solution
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   Lavadowashed with water and saturated brine
5. 5
   SecadoAfter drying on anhydrous sodium carbonate
6. 6
   Otroremoving the solvent
7. 7
   Otroby evaporation
8. 8
   Otrothe resulting orange solid was purified by a silica gel column chromatography (ether:hexane=3:1)
9. 9
   Otroto obtain a light orange solid which
10. 10
    Lavadowas subsequently washed with an ether-hexane (1:3) mixture solution

Procedimiento

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.

Fuente