Acetic Acid → 4-(4-Methyl-5-(methylsulfonyl)-4H-1,2,4-triazol-3-yl)pyridine

HRID 639782Notes

Reaction equation

HRID 639782 reaction equation
[CH3:1][N:2]1[C:6](SC)=[N:5][N:4]=[C:3]1[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1.[O-][Mn](=O)(=O)=O.[K+].[S:21]([O-:24])(O)=[O:22].[Na+].[C:26](O)(=O)C>O>[CH3:26][S:21]([C:6]1[N:2]([CH3:1])[C:3]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[N:4][N:5]=1)(=[O:24])=[O:22]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 8659874-(4-Methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)pyridineHCID 23665763Sodium Bisulfite

Product 1

HCID 221514774-(4-Methyl-5-(methylsulfonyl)-4H-1,2,4-triazol-3-yl)pyridineYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-(4-Methyl-5-methylsulfanyl-4H-[1,2,4]triazol-3-yl)-pyridine (1000 mg, 4.85 mmol) in acetic acid, added a solution of KMnO4 (1.15 g, 7.28 mmol) in H2O (50 mL) drop-wise. Stirred at RT for 3 hours. Added sodium hydrogen sulfite until purple colour was discharged. Extracted into chloroform (3×100 mL). Washed organic layer with saturated sodium bicarbonate (50 mL). Dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield title compound (1.01 g, 87% yield). 1H-NMR (CDCl3) δ (ppm): 8.89 (d, 2H), 7.64 (d, 2H), 4.05 (s, 3H), 3.64 (s, 3H).

Workup

  1. extractionExtracted into chloroform (3×100 mL)
  2. dry with materialDried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef67638fd1c8484da34894ee5894bbac
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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