Hydrochloric Acid → Pyridine-3-sulfonyl chloride hydrochloride

HRID 2196893Notes

Reaction equation

HRID 2196893 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:19])=O.Cl>C(Cl)(Cl)Cl>[ClH:12].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([Cl:19])(=[O:10])=[O:8])[CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acid

Product 1

HCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideYield 81%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-pyridinesulfonic acid (50.0 g), phosphorus pentachloride (80.0 g) and phosphorus oxychloride (100 mL) was stirred at 120° C. for 8 hr. Under a nitrogen atmosphere, the mixture was cooled to room temperature, and chloroform (dehydrated, 330 mL) was added. Hydrogen chloride was blown in, and the precipitated crystals were collected by filtration and washed with chloroform (dehydrated) to give the title compound as a white solid (yield 54.7 g, 81%).

Workup

  1. temperatureUnder a nitrogen atmosphere, the mixture was cooled to room temperature
  2. filtrationwere collected by filtration
  3. washwashed with chloroform (dehydrated)

Sources & evidence

ORD record
ord-d561592a6ac24f41b08966d6c9077c45
Source dataset
uspto-grants-2012_12
Patent number
US08338461B2

Reaction notes

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