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

HRID 2107328Notes

Reaction equation

HRID 2107328 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-c2bfb29ce0b44733ba1f6dedd5d1fd1f
Source dataset
uspto-grants-1990_06
Patent number
US04933458

Reaction notes

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