Phosphorus oxychloride → Pyridine-3-sulfonyl chloride

HRID 2293689Notes

Reaction equation

HRID 2293689 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].O=P(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

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acid

Product 1

HCID 3164136Pyridine-3-sulfonyl chlorideYield 67.2%

Procedure

To 1.2 g of 3-pyridine sulfonic acid (Aldrich Chemical Co.) is added 1.70 g of PCl5 and 5.4 ml of POCl3. The reaction mixture is heated to reflux temperature and allowed to stir at reflux for 5 hours. The reaction mixture is cooled to room temperature and evaporated to dryness under vacuum. The solid residue is distributed between methylene chloride and saturated aqueous sodium bicarbonate solution and the organic phase is washed twice with aqueous bicarbonate solution followed by drying over anhydrous sodium sulfate. The organic solution is evaporated to dryness to give 900 mg of the title compound which is used directly in the preparation of sulfonamides.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux temperature
  3. temperatureat reflux for 5 hours
  4. customevaporated to dryness under vacuum
  5. washthe organic phase is washed twice with aqueous bicarbonate solution
  6. dry with materialby drying over anhydrous sodium sulfate
  7. customThe organic solution is evaporated to dryness

Sources & evidence

ORD record
ord-245a8c662c7c4d989e584456d5763e4f
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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