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

HRID 639832Notes

Reaction equation

HRID 639832 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 r.t. the reaction was basified with 4M NaOH. 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-1c56794da5e74e969e17e292ac3b107b
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

Loading…