Phosphorus oxychloride → Pyridine-3-sulfonyl chloride

HRID 216302

Reaction equation

HRID 216302 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 chlorideYield 525.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-pyridinesulfonic acid (1.0 g, 6.3 mmol), phosphorous pentachloride (1.6 g, 1.2 mmol), and phosphorous oxychloride (2.0 mL, 3.3 mmol) was combined and stirred at 100° C. for 18 h. The reaction was cooled to 25° C., diluted with CHCl3, and bubbled with HCl gas. The resulting precipitate was collected by filtration, washed with CHCl3, and dried in vacuo to yield 1.12 g of the title compound (84%).

Workup

  1. temperatureThe reaction was cooled to 25° C.
  2. custombubbled with HCl gas
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with CHCl3
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e89e0e9e749040bbaf7c12a287bc3115
Source dataset
uspto-grants-2012_06
Patent number
US08193227B2

Linked notes

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