Water → Pyridine-2-sulfonyl Chloride

HRID 513367Notes

Reaction equation

HRID 513367 reaction equation
[Cl:1][O-].[Na+].[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1S.O.[OH:12][S:13]([OH:16])(=O)=O>>[N:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:13]([Cl:1])(=[O:16])=[O:12]

Participants

5

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 23665760Sodium HypochloriteHCID 178418616HCID 178418616, compound

Product 1

HCID 3787675Pyridine-2-sulfonyl ChlorideYield 50%

Procedure

Sodium hypochlorite solution (conc., 62 ml) was added dropwise to a stirred solution of pyridine-2-thiol (1.0 g, 8.995 mmol) dissolved in H2SO4 (25 ml) at 0° C. The mixture was stirred for 30 min, water (15 ml) added and the mixture extracted with DCM. The organic phases were combined, dried (MgSO4) and concentrated in vacuo gave the title compound (800 mg, 50%) which was used in the next step without purification. The structure was confirmed by 1H NMR.

Workup

  1. extractionthe mixture extracted with DCM
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d5d59080bf1435086a36180a29a82ae
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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