Water → HCID 25264241, compound

HRID 2422732Notes

Reaction equation

HRID 2422732 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[CH3:7][C:8]1[CH:13]=[N:12][C:11]([C:14]2[N:18]([CH3:19])[C:17]([S:20][CH3:21])=[N:16][N:15]=2)=[CH:10][N:9]=1.S([O-])(O)(=O)=[O:23].[Na+].[OH2:28]>C(O)(=O)C>[CH3:7][C:8]1[CH:13]=[N:12][C:11]([C:14]2[N:18]([CH3:19])[C:17]([S:20]([CH3:21])(=[O:23])=[O:28])=[N:16][N:15]=2)=[CH:10][N:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 516875Potassium PermanganateHCID 516919Sodium BisulfateHCID 25264103HCID 25264103, compound

Product 1

HCID 25264241HCID 25264241, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of potassium permanganate (3.38 g, 17.0 mmol) in water (95 mL) was added to a solution of 2-methyl-5-[4-methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl]pyrazine (1.853 g, 11.52 mmol) in glacial acetic acid (45 mL). The resulting mixture was stirred at room temperature overnight. Solid sodium hydrogen sulfate was added in portions until the dark color disappeared giving a clear colorless solution. The product was partitioned between chloroform (350 mL) and water (50 mL), and the aqueous layer was extracted with chloroform (3×150 mL). The combined organic layer was neutralized with aq. NaOH (40 is mL, 6M) and saturated sodium bicarbonate (250 mL) until gas evolution ceased and pH ˜7. The organic layer was washed with brine (100 mL) and dried over sodium sulfate. Removal of the solvent in vacuo yielded the title compound (2.715 g, 93%, white solid). 1H NMR (300 MHz): 9.44 (s, 1H), 8.55 (s, 1H), 4.36 (s, 3H), 3.62 (s, 3H), 2.69 (s, 3H).

Workup

  1. customdisappeared giving a clear colorless solution
  2. customThe product was partitioned between chloroform (350 mL) and water (50 mL)
  3. extractionthe aqueous layer was extracted with chloroform (3×150 mL)
  4. washThe organic layer was washed with brine (100 mL)
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-bfb4619fced8444ea2eb6d29aa65cc47
Source dataset
uspto-grants-2011_06
Patent number
US07960422B2

Reaction notes

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