Phosphorus pentachloride → Pyridine-3-sulfonyl chloride

HRID 1608780Notes

Reaction equation

HRID 1608780 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]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[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 2

HCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acid

Product 1

HCID 3164136Pyridine-3-sulfonyl chlorideYield 92%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1140TolueneSolvent

Procedure

3-pyridylsulfonic acid (30 g, 0.188 mole) was added to PCl5 (46.8 g, 0.225 mole), suspended in 150 mL toluene and heated to reflux overnight. The suspension was cooled and concentrated to yield a yellow oil, which was diluted with benzene, filtered through a pad of celite and concentrated to give 30.7 g (92%) of 2-15 as a yellow oil, which was used in the next step without purification.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureThe suspension was cooled
  4. concentrationconcentrated
  5. customto yield a yellow oil, which
  6. filtrationfiltered through a pad of celite
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ca4f89658cab4c5b9be4eeb8b030f373
Source dataset
uspto-grants-1995_03
Patent number
US05397791

Reaction notes

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