Methanol → 4-(5-Methanesulfonyl-4-methyl-4h-[1,2,4]triazol-3-yl)-2-methoxy-pyridine

HRID 500546Notes

Reaction equation

HRID 500546 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:13]([CH3:14])[C:12](SC)=[N:11][N:10]=2)[CH:6]=[CH:5][N:4]=1.O[O:18][S:19]([O-:21])=O.[K+].S([O-])(O[O-])(=O)=O.[K+].[K+].[CH3:31]O>O>[CH3:31][S:19]([C:12]1[N:13]([CH3:14])[C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=2)=[N:10][N:11]=1)(=[O:21])=[O:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 10313463Potassium peroxymonosulphateHCID 23707502Potassium hydroxy sulfiteHCID 248517082-Methoxy-4-(4-methyl-5-methylsulfanyl-4h-[1,2,4]triazol-3-yl)-pyridine

Product 1

HCID 248518124-(5-Methanesulfonyl-4-methyl-4h-[1,2,4]triazol-3-yl)-2-methoxy-pyridineYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound of example 25.1 (21.97 g, 92.97 mmol) was partially dissolved in methanol (500 mL) and OXONE® (potassium peroxomonosulfate compound, 114.3 g, 186.0 mmol) dissolved in water (500 mL) was added slowly. The reaction mixture stirred for 5 hours. The reaction was partially concentrated, poured into water and extracted with chloroform. The organic extracts were dried, filtered and concentrated to afford the title compound (22 g, 93%) as a white solid.

Workup

  1. additionwas added slowly
  2. concentrationThe reaction was partially concentrated
  3. additionpoured into water
  4. extractionextracted with chloroform
  5. customThe organic extracts were dried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d4a2b11b39e84215a1fcec443b3fdc39
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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