m-Chloroperbenzoic acid → 2-(2-Pyridylmethylsulfinyl)quinoxaline

HRID 1030786Notes

Reaction equation

HRID 1030786 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9][C:10]1[CH:19]=[N:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.ClC1C=CC=C(C(OO)=[O:28])C=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][S:9]([C:10]1[CH:19]=[N:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1)=[O:28]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 140521712-(2-Pyridylmethylthio)quinoxaline hydrochloride

Product 1

HCID 140521732-(2-Pyridylmethylsulfinyl)quinoxalineYield 11.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

In a mixture of 20 ml of chloroform and 5 ml of methanol was dissolved 2.51 g of 2-(2-pyridylmethylthio)-quinoxaline hydrochloride. To the chilled solution kept at a temperature of lower than 0° C. (temperature of solution) was portionwise added 1.95 g of m-chloroperbenzoic acid (purity: 70%). After the reaction was complete, chloroform and saturated aqueous NaHCO3 solution were added to the reaction mixture. 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 (acetone/hexane), and recrystallized from ethanol/ether to give 0.27 g of 2-(2-pyridylmethylsulfinyl)quinoxaline as a pale brown crystalline powder, m.p. 117°-122° C. (decompn.).

Workup

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

Sources & evidence

ORD record
ord-652d49f0b2e743d4b9eeab171f054459
Source dataset
uspto-grants-1992_04
Patent number
US05106976

Reaction notes

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