Sulfuric Acid → Pyridine-2-sulfonyl Chloride

HRID 1782225Notes

Reaction equation

HRID 1782225 reaction equation
S[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[S:8](=[O:12])(=O)(O)[OH:9].[Cl:13][O-].[Na+]>O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[S:8]([Cl:13])(=[O:12])=[O:9]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 23665760Sodium HypochloriteHCID 178418616HCID 178418616, compound

Product 1

HCID 3787675Pyridine-2-sulfonyl ChlorideYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, 2-mercaptopyridine (2.0 g) was added to sulfuric acid (50 mL) and the mixture was stirred. Sodium hypochlorite solution (chlorine content 5%, 126 mL) was added dropwise over 1.5 hr, and the mixture was further stirred at the same temperature for 30 min. The reaction mixture was diluted with water (100 mL), and extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound as a colorless oil (yield 2.45 g, 77%).

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe mixture was further stirred at the same temperature for 30 min
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef15361f7a62441d899e6da0afee91eb
Source dataset
uspto-grants-2009_03
Patent number
US07498337B2

Reaction notes

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