Reaction #2502

Reaction equation

sodium carbonate

pyridine

o-Anisidine

3-pyridinesulfonylchloride hydrochloride

→

title compound

Yield 83.5%

N-(2-Methoxyphenyl)-3-pyridinesulfonamide

Yield 83.5%

Solvents

water

toluene

Conditions

Workup

1. 1
   Otherat room temperature
2. 2
   Otherthe resulting reaction solution
3. 3
   Extractionextracted with ethyl acetate
4. 4
   Washwashed with water and saturated brine
5. 5
   DryingAfter drying on anhydrous sodium carbonate
6. 6
   Otherremoving the solvent
7. 7
   Otherby evaporation
8. 8
   Otherthe resulting orange solid was purified by a silica gel column chromatography (ether:hexane=3:1)
9. 9
   Otherto obtain a light orange solid which
10. 10
    Washwas subsequently washed with an ether-hexane (1:3) mixture solution

Procedure

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.

Source