Water → 2-(2-Pyridylmethylthio)quinoxaline hydrochloride

HRID 1030785Notes

Reaction equation

HRID 1030785 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.Cl.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[ClH:20].[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=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 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 23392Picolyl chloride hydrochlorideHCID 178418602HCID 178418602, compound

Product 1

HCID 140521712-(2-Pyridylmethylthio)quinoxaline hydrochlorideYield 58.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 50 ml of acetone was dissolved 2.0 g of 2-mercaptoquinoxaline. To the solution were added 2.02 g of 2-picolyl chloride hydrochloride, 4.0 g of potassium carbonate and 5 ml of water. The resulting mixture was stirred at room temperature for 0.5 hr., and the solvent was removed under reduced pressure. The residue was extracted with chloroform after addition of chloroform and water. The organic layer was separated and dried over sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was placed under reduced pressure to remove the solvent. To the residue were added 20 ml of ethanol and 1.03 ml of conc. hydrochloric acid and then added ether. Thus precipitated crystals were washed with ethanol-ether (1:1) and dried under reduced pressure to give 2.09 g of 2-(2-pyridylmethylthio)quinoxaline hydrochloride as a yellow crystalline powder.

Workup

  1. custom, and the solvent was removed under reduced pressure
  2. extractionThe residue was extracted with chloroform
  3. additionafter addition of chloroform and water
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. customThe sodium sulfate was removed by filtration
  7. customto remove the solvent
  8. additionTo the residue were added 20 ml of ethanol and 1.03 ml of conc. hydrochloric acid
  9. washThus precipitated crystals were washed with ethanol-ether (1:1)
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-c71603636a344b678bcb0703817eb868
Source dataset
uspto-grants-1992_04
Patent number
US05106976

Reaction notes

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