Acetone → 2-(methylsulfonyl)-5-nitropyridine

HRID 1815106Notes

Reaction equation

HRID 1815106 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][C:7](SC)=[CH:8][CH:9]=1)([O-:3])=[O:2].[S:12](=[O:16])(=O)(O)[OH:13].[Mn]([O-])(=O)(=O)=O.[K+].[CH3:23]C(C)=O>>[N+:1]([C:4]1[CH:5]=[N:6][C:7]([S:12]([CH3:23])(=[O:16])=[O:13])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 180AcetoneHCID 1118Sulfuric AcidHCID 516875Potassium PermanganateHCID 44393132-(Methylthio)-5-nitropyridine

Product 1

HCID 12115522-(methylsulfonyl)-5-nitropyridineYield 70%

Procedure

3-Nitro-6-(methylthio)pyridine (22.0 g, 129.3 mmol) was dissolved in acetone (140 mL). Sulfuric acid (2N, 230 mL) was then added dropwise to above solution to form a slurry. Potassium permanganate (KMnO4) (26.5 g, 168.1 mmol, dissolved in 500 mL of H2O) was added to the above mixture dropwise. The mixture that resulted was stirred at room temperature overnight. The solid was filtered and stirred with a warm mixture of ethanol/methanol (10/1). The insoluble salt was filtered, the filtrate was concentrated to provide a pale yellow solid. The crude product was recrystallized from ethanol to furnish the title compound (17.8 g, 70%).

Workup

  1. customto form a slurry
  2. customThe mixture that resulted
  3. filtrationThe solid was filtered
  4. stirringstirred with a warm mixture of ethanol/methanol (10/1)
  5. filtrationThe insoluble salt was filtered
  6. concentrationthe filtrate was concentrated
  7. customto provide a pale yellow solid
  8. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-184344a4be344a1ba1cf612f3b1acbe9
Source dataset
uspto-grants-2005_04
Patent number
US06878726B2

Reaction notes

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