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

HRID 2107326Notes

Reaction equation

HRID 2107326 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[CH2:5][S:6][C:7]1[CH:16]=[N:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1.ClC1C=CC=C(C(OO)=[O:30])C=1>C(Cl)(Cl)Cl>[CH3:1][N:2]([CH3:21])[C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[CH2:5][S:6]([C:7]1[CH:16]=[N:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=1)=[O:30]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 140521762-(2-Dimethylaminobenzylthio)quinoxaline

Product 1

HCID 140521812-(2-Dimethylaminobenzylsulfinyl)quinoxalineYield 21.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 50 ml of chloroform was dissolved 1.47 g of 2-(2-dimethylaminobenzylthio)quinoxaline. To the chilled solution kept at -10° C. was portionwise added 1.54 g of m-chloroperbenzoic acid (purity: 80%). To the reaction liquid were washed successively with saturated aqueous NaHCO3 solution, water and saturated aqueous sodium chloride solution, 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 (hexane/acetone) to give 330 mg of 2-(2-dimethylaminobenzylsulfinyl)quinoxaline as a yellow powder, m.p. 114°-115° C.

Workup

  1. customkept at -10° C.
  2. customTo the reaction liquid
  3. washwere washed successively with saturated aqueous NaHCO3 solution, water and saturated aqueous sodium chloride solution
  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 (hexane/acetone)

Sources & evidence

ORD record
ord-65639372115f4d2d8a329ec85f0b7150
Source dataset
uspto-grants-1990_06
Patent number
US04933458

Reaction notes

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