m-Chloroperbenzoic acid → 3-Methyl-2-(2-pyridylmethylsulfinyl)quinoxaline

HRID 1030788Notes

Reaction equation

HRID 1030788 reaction equation
Cl.[CH3:2][C:3]1[C:4]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.ClC1C=CC=C(C(OO)=[O:29])C=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[CH3:2][C:3]1[C:4]([S:13]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[O:29])=[N:5][C:6]2[C:11]([N:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14052175HCID 14052175, compound

Product 1

HCID 140521803-Methyl-2-(2-pyridylmethylsulfinyl)quinoxalineYield 67.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

In a mixture of 36 ml of chloroform and 18 ml of methanol was dissolved 2.6 g of 3-methyl-2-(2-pyridylmethylthio)quinoxaline hydrochloride. To the chilled solution kept at a temperature of lower than 0° C. (temperature of solution) was added 1.77 g of m-chloroperbenzoic acid (purity 70%). After the reaction was complete, chloroform and saturated aqueous NaHCO3 solution were added to the reaction mixture under chilling. The organic layer was separated and dried over sodium sulfate. The sodium sulfate was then removed by filtration, and the solvent was evaporated under reduced pressure from the filtrate. The residue was purified by silica gel column chromatography (chloroform/methanol), and recrystallized from ether/hexane to give 1.63 g of 3-methyl-2-(2-pyridylmethylsulfinyl)quinoxaline as an orange crystalline powder, m.p. 85°-88° C. (decompn.).

Workup

  1. customlower than 0° C.
  2. temperatureunder chilling
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. customThe sodium sulfate was then removed by filtration
  6. customthe solvent was evaporated under reduced pressure from the filtrate
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol)
  8. customrecrystallized from ether/hexane

Sources & evidence

ORD record
ord-4a895d9082764cfb8996b5edf49c7236
Source dataset
uspto-grants-1992_04
Patent number
US05106976

Reaction notes

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