Chloroform → 3-[5-(Methanesulfonyl)-4-methyl-4H-1,2,4-triazol-3-yl]pyridine

HRID 732086Notes

Reaction equation

HRID 732086 reaction equation
[O-:1][Mn](=O)(=O)=O.[K+].[CH3:7][N:8]1[C:12]([S:13][CH3:14])=[N:11][N:10]=[C:9]1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[OH-:21].[Na+].C(Cl)(Cl)Cl>O.C(O)(=O)C>[CH3:7][N:8]1[C:12]([S:13]([CH3:14])(=[O:1])=[O:21])=[N:11][N:10]=[C:9]1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 404246263-(4-Methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)pyridine

Product 1

HCID 469283343-[5-(Methanesulfonyl)-4-methyl-4H-1,2,4-triazol-3-yl]pyridineYield 53%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

KMnO4 (5 g, 32 mmol) was added to a solution of 3-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl]pyridine (6.0 g, 29 mmol) in H2O (40 mL) and acetic acid (100 mL). After 1 h stirring at rt the reaction was basified with aq. NaOH (4M). CHCl3 was added and the mixture was filtrated through celite. The layers were separated and the water phase was washed with CHCl3. The combined organic phase was dried and concentrated to give 3.67 g (53%) of the title compound. 1H NMR: 3.59 (s, 3H) 3.99 (s, 3H) 7.52 (m, 1H) 8.02 (dt, 1H) 8.83 (dd, 1H) 8.91 (m, 1H)

Workup

  1. filtrationthe mixture was filtrated through celite
  2. customThe layers were separated
  3. washthe water phase was washed with CHCl3
  4. customThe combined organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6294cd95bcec49d2a07551f1e036507c
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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