Sodium Chloride → 6-Chloro-3-pyridinesulfinic acid

HRID 567645Notes

Reaction equation

HRID 567645 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.S([O-])([O-])=O.[Na+].[Na+].S(Cl)(Cl)(=O)=O.[OH-].[Na+].[Cl-].[Na+]>O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([OH:10])=[O:9])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 24437Sodium SulfiteHCID 24648Sulfuryl chloride2×HCID 27927922-Chloro-5-pyridinesulfonyl chloride

Product 1

HCID 212621546-Chloro-3-pyridinesulfinic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Finely powdered 6-chloro-3-pyridinesulfonyl chloride (1), (20 g, 94.31 mMole) was gradually added over a 30 minute period, to a solution of sodium sulfite (12 g, 94.31 mMole) in water (200 mL), with good stirring. During the addition of the sulfonyl chloride the temperature of the solution was maintained at approximately 20° C. with the aid of ice/water and the pH kept at approximately 7 with the addition of 3N-sodium hydroxide (50-60 mL). After all of the sulfonyl chloride had been added the resulting solution was stirred at room temperature for an additional 60 minutes. To the solution was then added solid sodium chloride to get a near saturated solution which was then stored at 4° C. overnight. The solid product was then filtered off and air dried. Yield 18.1 g.

Workup

  1. customto get a near saturated solution which
  2. waitwas then stored at 4° C. overnight
  3. filtrationThe solid product was then filtered off
  4. customair dried

Sources & evidence

ORD record
ord-07adab9aab5f4d25a05dfe0a7c5dc9c3
Source dataset
uspto-grants-2001_01
Patent number
US06180331B2

Reaction notes

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