Sodium Chloride → Pyridine-3-sulfonyl chloride

HRID 1293599Notes

Reaction equation

HRID 1293599 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].P(Cl)(Cl)(Cl)=O.C([O-])(O)=O.[Na+].[Na+].[Cl-]>COC(C)(C)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([Cl:12])(=[O:10])=[O:8])[CH:2]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 694683-Pyridinesulfonic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 3164136Pyridine-3-sulfonyl chlorideYield 94.3%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A mixture of pyridine-3-sulfonic acid (10.3 g, 64.8 mmol), phosphorus pentachloride (20.82 g, 100 mmol) and phosphorus oxychloride (10 mL, 109 mmol) was heated to reflux for 3 h (according to J. Org. Chem. 1989, 54(2), 389.). Evaporated to dryness to give a yellow solid, dissolved in ice water and methyl-tert-butyl ether, added cautiously sat. NaHCO3-sol. until neutralized, saturated with solid NaCl, separated phases, dried organic layer over Na2SO4. Removal of the solvent in vacuum to give the title compound as an orange liquid (10.85 g, 94%). MS (ISP) 178.1 [(M+H)+] and 180.0 [(M+2+H)+].

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h (according to J. Org. Chem. 1989, 54(2), 389.)
  3. customEvaporated to dryness
  4. customto give a yellow solid
  5. customseparated phases, dried organic layer over Na2SO4
  6. customRemoval of the solvent in vacuum

Sources & evidence

ORD record
ord-c1274e34c496458b817871e47f0330f3
Source dataset
uspto-grants-2007_07
Patent number
US07238808B2

Reaction notes

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