m-Chloroperbenzoic acid → HCID 14052183, compound

HRID 2107329Notes

Reaction equation

HRID 2107329 reaction equation
[CH3:1][N:2]([CH3:24])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][S:6][C:7]1[C:16]([CH3:17])=[N:15][C:14]2[C:9](=[CH:10][C:11]([CH3:19])=[C:12]([CH3:18])[CH:13]=2)[N:8]=1.ClC1C=CC=C(C(OO)=[O:33])C=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[CH3:24][N:2]([CH3:1])[C:3]1[CH:23]=[CH:22][CH:21]=[CH:20][C:4]=1[CH2:5][S:6]([C:7]1[C:16]([CH3:17])=[N:15][C:14]2[C:9](=[CH:10][C:11]([CH3:19])=[C:12]([CH3:18])[CH:13]=2)[N:8]=1)=[O:33]

Participants

6

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 14052178HCID 14052178, compound

Product 1

HCID 14052183HCID 14052183, compoundYield 28.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

In a mixture of 35 ml of chloroform and 3 ml of methanol was dissolved 3.71 g of 2-(2-dimethylaminobenzylthio)-3,6,7-trimethylquinoxaline. To the chilled solution kept at a temperature of lower than 0° C. (temperature of solution) was slowly added 2.45 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 (acetone/hexane). The eluate was concentrated and the resulting residue was crystallized from ether/hexane to give 1.12 g of 2-(2-dimethylaminobenzylsulfinyl)-3,6,7-trimethylquinoxaline as a yellow crystalline powder, m.p. 83°-88° 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. concentrationThe eluate was concentrated
  8. customthe resulting residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-7a0ea1d1876441f588c1476408fdafa9
Source dataset
uspto-grants-1990_06
Patent number
US04933458

Reaction notes

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