m-Chloroperbenzoic acid → HCID 22096352, compound

HRID 875239Notes

Reaction equation

HRID 875239 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1SC.C([O-])(O)=O.[Na+].C1C=C(Cl)C=C(C(OO)=O)C=1.[O-:25][S:26]([O-:29])(=S)=O.[Na+].[Na+].[C:32]([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH3:1][N:2]1[CH:6]=[N:5][N:4]=[C:3]1[S:26]([CH3:32])(=[O:29])=[O:25]

Participants

6

Reactant 4

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 582063HCID 582063, compoundHCID 20482104HCID 20482104, compound

Product 1

HCID 22096352HCID 22096352, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methyl-3-(methylsulfanyl)-4H-1,2,4-triazole (31 g, 239.96 mmol, 1 eq.) in 1000 ml of DCM cooled to 0° C. was added NaHCO3 (42.33 g, 503.92 mmol, 2.1 eq.) followed by m-CPBA (70%, 118.31 g, 479.92 mmol, 2.0 eq.) portion wise. The reaction was warmed to r.t. and stirred. A sat. aqueous 1/1 Na2S2O3/Na2CO3 solution was added slowly and the mixture stirred 15 min. The layers were separated and the organics were washed with H2O, dried over MgSO4 and concentrated. The crude was triturated in IPE and filtered to give 4-methyl-3-(methylsulfonyI)-4H-1,2,4-triazole (9.35 g, 59% yield) as yellow solid.

Workup

  1. stirringthe mixture stirred 15 min
  2. customThe layers were separated
  3. washthe organics were washed with H2O
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude was triturated in IPE
  7. filtrationfiltered

Sources & evidence

ORD record
ord-59644be1e0ab44adb9f29093c8cf8e2e
Source dataset
uspto-grants-2015_03
Patent number
US08981111B2

Reaction notes

Loading…