Hydrochloric Acid → N-(5-Bromo-2-methoxypyridin-3-yl)-4-hydroxybenzenesulfonamide

HRID 1052475Notes

Reaction equation

HRID 1052475 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:5](Cl)=[N:6][CH:7]=1.C[O-].[Na+].[C:23](=O)(O)[O-:24].[Na+].Cl>>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:5]([O:24][CH3:23])=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 90102863N-(5-Bromo-2-chloropyridin-3-yl)-4-hydroxybenzenesulfonamide

Product 1

HCID 90102089N-(5-Bromo-2-methoxypyridin-3-yl)-4-hydroxybenzenesulfonamideYield 82%

Procedure

N-(5-Bromo-2-chloropyridin-3-yl)-4-hydroxybenzenesulfonamide (587 mg, 1.61 mmol) and sodium methoxide (25% in methanol, 10 ml, 43.73 mmol) were stirred at 120° C. for 20 min under microwave conditions. The reaction mixture was poured into sodium bicarbonate saturated solution, neutralized with concentrated chlorohydric acid and extracted with ethyl acetate (×3). The organic phase was dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure to obtain 475 mg (82% yield, 100% purity) of the title compound, which was used in the next synthetic step without further purification.

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-0d77775763a84a04a3f86fb4c6d697a0
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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