Phosphorus pentachloride → Pyridine-3-sulfonyl chloride hydrochloride

HRID 1447069Notes

Reaction equation

HRID 1447069 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]>>[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

3

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acid

Product 1

HCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideYield 148.7%

Procedure

A mixture of 34.0 g (0.21 mol) of 3-pyridinesulfonic acid and 47 g (0.24 mol) of phosphorus pentachloride is heated on the steam bath for 2 hrs and the phosphorus oxychloride is removed at reduced pressure to give an oil which crystallize upon addition of chloroform. The solid is filtered, washed with chloroform, and dried under high vacuum to give 38.2 g of 3-pyridinesulfonyl chloride hydrochloride.

Workup

  1. temperatureis heated on the steam bath for 2 hrs
  2. customthe phosphorus oxychloride is removed at reduced pressure
  3. customto give an oil which
  4. customcrystallize upon addition of chloroform
  5. filtrationThe solid is filtered
  6. washwashed with chloroform
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-379cda865f1f41b8b91f29dd52b28910
Source dataset
uspto-grants-1982_02
Patent number
US04315014

Reaction notes

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