Sulfuric Acid → Pyridine-2-sulfonyl Chloride

HRID 1962500Notes

Reaction equation

HRID 1962500 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-d0cbbaa2ada64719a884c66069f9607a
Source dataset
uspto-grants-2013_04
Patent number
US08415368B2

Reaction notes

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