m-Chloroperbenzoic acid → 2-(2-Dimethylaminobenzylsulfinyl)-3-methylquinoxaline

HRID 1030794Notes

Reaction equation

HRID 1030794 reaction equation
Cl.[CH3:2][N:3]([CH3:23])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH2:6][S:7][C:8]1[C:17]([CH3:18])=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1.ClC1C=CC=C(C(OO)=[O:32])C=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[CH3:23][N:3]([CH3:2])[C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[CH2:6][S:7]([C:8]1[C:17]([CH3:18])=[N:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:32]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 19820959HCID 19820959, compound

Product 1

HCID 140521822-(2-Dimethylaminobenzylsulfinyl)-3-methylquinoxalineYield 31.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

In a mixture of 10 ml of chloroform and 10 ml of methanol was dissolved 1.73 g of 2-(2-dimethylaminobenzylthio)-3-methylquinoxaline hydrochloride. To the chilled solution kept at a temperature of lower than 0° C. (temperature of solution) was portionwise added 1.14 g of m-chloroperbenzoic acid (purity: 80%). 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 (chloroform/methanol), and recrystallized from ethyl acetate/hexane to give 0.51 g of 2-(2-dimethylaminobenzylsulfinyl)-3-methylquinoxaline as a pale brown crystalline powder, m.p. 68°-70° 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 (chloroform/methanol)
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-1d0db769d9c24b9dab42ca65ee1904c7
Source dataset
uspto-grants-1992_04
Patent number
US05106976

Reaction notes

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