Phosphorus pentachloride → Pyridine-3-sulfonyl chloride

HRID 36649

Reaction equation

HRID 36649 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 23-10 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-bf556213779245328caa8e5257c096ab
Source dataset
uspto-grants-1995_05
Patent number
US05416099

Linked notes

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