Sodium Hydroxide → 2-(2-Dimethylaminobenzylthio)quinoxaline

HRID 1030791Notes

Reaction equation

HRID 1030791 reaction equation
[SH:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[OH-].[Na+].Cl.[CH3:15][N:16]([CH3:25])[C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19]Cl>C(O)C.O>[CH3:15][N:16]([CH3:25])[C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH2:19][S:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 135374262-(chloromethyl)-N,N-dimethylaniline hydrochlorideHCID 178418602HCID 178418602, compound

Product 1

HCID 140521762-(2-Dimethylaminobenzylthio)quinoxalineYield 82.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1 g of 2-mercaptoquinoxaline in 40 ml of ethanol was added a solution of 530 mg of sodium hydroxide in 2 ml of water, and subsequently added 1.27 g of 2-dimethylaminobenzyl chloride hydrochloride. The resulting mixture was stirred at room temperature for 18 hrs., and the solvent was removed under reduced pressure. The residue was extracted with ethyl acetate. The organic layer was washed successively with 5% aqueous sodium hydroxide solution, water, and saturated aqueous sodium chloride solution, and dried over sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was placed under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (hexane/acetone) to give 1.5 g of 2-(2-dimethylaminobenzylthio)quinoxaline as a yellow oil.

Workup

  1. custom, and the solvent was removed under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. washThe organic layer was washed successively with 5% aqueous sodium hydroxide solution, water, and saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customThe sodium sulfate was removed by filtration
  6. customto remove the solvent
  7. customThe residue was purified by silica gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-85889084feb74a759c005289ea0f67ad
Source dataset
uspto-grants-1992_04
Patent number
US05106976

Reaction notes

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