Phosphorus pentachloride → Pyridine-3-sulfonyl chloride

HRID 2363831Notes

Reaction equation

HRID 2363831 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13]([OH:16])(=O)=[O:14])[CH:8]=1>C1(C)C=CC=CC=1>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13]([Cl:2])(=[O:16])=[O:14])[CH:8]=1

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acid

Product 1

HCID 3164136Pyridine-3-sulfonyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorus pentachloride (1.57 g, 7.5 mmol) was added to a stirred solution of pyridine-3-sulfonic acid (1.00 g, 6.3 mmol) in toluene (5 mL). The mixture was heated at reflux for 16 hours and then cooled to room temperature. The mixture was filtered through celite, and the celite was washed with benzene (2×10 mL). The combined filtrates were concentrated under reduced pressure to give crude pyridine-3-sulfonyl chloride (0.70 g, 100%), which was used directly in the next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. filtrationThe mixture was filtered through celite
  4. washthe celite was washed with benzene (2×10 mL)
  5. concentrationThe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-dc2a2acacdc14dc4a1931762f1ed8e4d
Source dataset
uspto-grants-2014_04
Patent number
US08691993B2

Reaction notes

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