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

HRID 1052490Notes

Reaction equation

HRID 1052490 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.[O-:20][CH2:21][CH3:22].[Na+].C(=O)(O)[O-].[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:20][CH2:21][CH3:22])=[N:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 90102863N-(5-Bromo-2-chloropyridin-3-yl)-4-hydroxybenzenesulfonamide

Product 1

HCID 90102657N-(5-Bromo-2-ethoxypyridin-3-yl)-4-hydroxybenzenesulfonamideYield 94%

Procedure

N-(5-Bromo-2-chloropyridin-3-yl)-4-hydroxybenzenesulfonamide (264 mg, 0.55 mmol) and sodium ethoxide (21% in ethanol, 10 ml, 27 mmol) were stirred at 120° C. for 90 min under microwave conditions. The reaction mixture was poured into sodium bicarbonate saturated solution, neutralized with concentrated chlorhydric 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 211 mg (94% yield, 91% 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-9a04d210610642acb311622cd4d5b97f
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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