Phosphorus pentachloride → Pyridine-3-sulfonyl chloride

HRID 464980

Reaction equation

HRID 464980 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]>>[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 3164136Pyridine-3-sulfonyl chloride

Procedure

A mixture of pyridine-3-sulphonic acid (3.0 g) and PCl5 (7.9 g) was stirred in an oil bath maintained at 150° for 3 hours, in a flask fitted with a reflux condenser. After cooling, the liquid formed set solid. The solid was triturated with xylene (10 cm3) and evaporated at the water pump in an oil-bath maintained at a maximum temperature of 110°, and with a splash-head to reduce frothing. The evaporation was repeated twice more, and the residue was pumped on a rotary evaporator to remove the last traces of xylene. The yellow, semi-crystalline mass (6.87 g) occluded unreacted PCl5.

Workup

  1. temperaturemaintained at 150° for 3 hours, in a flask
  2. customfitted with a reflux condenser
  3. temperatureAfter cooling
  4. customthe liquid formed
  5. customThe solid was triturated with xylene (10 cm3)
  6. customevaporated at the water pump in an oil-bath
  7. temperaturemaintained at a maximum temperature of 110°
  8. customThe evaporation
  9. customthe residue was pumped on a rotary evaporator
  10. customto remove the last traces of xylene

Sources & evidence

ORD record
ord-065341b76e4140eaa6075ac04359262f
Source dataset
uspto-grants-1985_10
Patent number
US04550114

Linked notes

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