Hydrochloric Acid → Pyridine-3-sulfonyl chloride hydrochloride

HRID 2090618Notes

Reaction equation

HRID 2090618 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-1c3b9ad4b9bf42ec90dcefe2a9fef808
Source dataset
uspto-grants-2013_05
Patent number
US08436187B2

Reaction notes

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