Phosphorus oxychloride → Pyridine-3-sulfonyl chloride

HRID 1018003Notes

Reaction equation

HRID 1018003 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([OH:10])(=O)=[O:8])[CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12].P(Cl)(Cl)(Cl)=O>C(Cl)(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([Cl:12])(=[O:10])=[O:8])[CH:2]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acid

Product 1

HCID 3164136Pyridine-3-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of pyridine-3-sulphonic acid (5.0 g), phosphorous pentachloride (8.0 g), phosphorous oxychloride (30 ml) and chloroform (30 ml) was stirred at 120° C. for 18 hours. The reaction mixture was cooled to room temperature then diluted with chloroform (30 ml) and then filtered. Hydrogen chloride gas was bubbled through the filtrate for 15 minutes and the resultant precipitate collected. This material was dried in vacuo to give the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customHydrogen chloride gas was bubbled through the filtrate for 15 minutes
  4. customthe resultant precipitate collected
  5. customThis material was dried in vacuo

Sources & evidence

ORD record
ord-a573817ce0e143eea3ea7af56806b9c4
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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