Phosphorus pentachloride → Pyridine-3-sulfonyl chloride hydrochloride

HRID 1159772Notes

Reaction equation

HRID 1159772 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.C(Cl)(Cl)Cl.Cl>[ClH:12].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([Cl:12])(=[O:10])=[O:8])[CH:2]=1

Participants

6

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acid

Product 1

HCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideYield 83%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6212ChloroformSolventHCID 24813Phosphorus oxychlorideSolvent

Conditions

Temperature
120 °C

Procedure

Pyridine-3-sulfonic acid (3.00 g, 18.8 mmol) and PCl5 (4.79 g, 23.0 mmol) were mixed in POCl3 (6 mL). The reaction was stirred and refluxed at 120° C. over night (15 h). Cooled to rt., diluted with CHCl3 (20 mL) and saturated with HCl (g). This gave a white precipitation, which was filtered off, washed with CHCl3 and dried under reduced pressure to give the title compound (3.36 μg, 83%) as a white powder.

Workup

  1. temperatureCooled to rt
  2. customThis gave
  3. customa white precipitation, which
  4. filtrationwas filtered off
  5. washwashed with CHCl3
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-417eb591bffe447ab1e8e83ceee081e2
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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