Phosphorus oxychloride → Pyridine-3-sulfonyl chloride

HRID 513366

Reaction equation

HRID 513366 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13]([OH:16])(=O)=[O:14])[CH:8]=1.P(Cl)(Cl)([Cl:19])=O>>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:13]([Cl:19])(=[O:16])=[O:14])[CH:8]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acid

Product 1

HCID 3164136Pyridine-3-sulfonyl chlorideYield 36%

Conditions

Temperature
130 °C

Procedure

Phosphorus pentachloride (3.0 g, 14.6 mmol) was added to a solution of 3-pyridinesulfonic acid (1.5 g, 9.42 mmol) dissolved in phosphoryl trichloride (2.45 g, 16.0 mmol) and the mixture heated to 130° C. for 3 h under argon. The mixture was concentrated in vacuo, the residue was quenched over ice and extracted with ether. The organic phase was washed with a saturated sodium bicarbonate solution and concentrated in vacuo to give the crude title compound (0.6 g, 36%) which was used immediately without purification.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was quenched over ice
  3. extractionextracted with ether
  4. washThe organic phase was washed with a saturated sodium bicarbonate solution
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-750efa81a63c45cd9af11ee4b49a53ee
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Linked notes

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