Sodium Hydroxide → HCID 14052179, compound

HRID 1030796Notes

Reaction equation

HRID 1030796 reaction equation
[OH-].[Na+].[SH:3][C:4]1[C:13]([CH3:14])=[N:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.Cl.[CH2:16]([N:18]([CH2:27][CH3:28])[C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Cl)[CH3:17]>O.C(O)C>[CH2:27]([N:18]([CH2:16][CH3:17])[C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][S:3][C:4]1[C:13]([CH3:14])=[N:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:28]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 14839433HCID 14839433, compoundHCID 1784186273-Methylquinoxaline-2-thiol

Product 1

HCID 14052179HCID 14052179, compoundYield 60.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 0.73 g of sodium hydroxide in a mixture of 2 ml of water and 50 ml of ethanol were added successively 1.5 g of 2-mercapto-3-methylquinoxaline and 1.99 g of 2-diethylaminobenzyl chloride hydrochloride. The resulting mixture was stirred at room temperature for 3 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 then dried over sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was placed under reduced pressure to remove the solvent. The residual oil was purified by silica gel column chromatography (hexane/acetone) to give 1.74 g of 2-(2-diethylaminobenzylthio)-3-methylquinoxaline 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 residual oil was purified by silica gel column chromatography (hexane/acetone)

Sources & evidence

ORD record
ord-58d8f68a37f14ddebf6ed2e986b8ac40
Source dataset
uspto-grants-1992_04
Patent number
US05106976

Reaction notes

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