2-Mercaptoethanol → 2-(7-Methoxy-quinoxalin-2-ylsulfanyl)-ethanol

HRID 1019913Notes

Reaction equation

HRID 1019913 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].Cl[C:6]1[CH:15]=[N:14][C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[CH:11][CH:12]=2)[N:7]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.CCCCCC>[CH3:17][O:16][C:10]1[CH:9]=[C:8]2[C:13]([N:14]=[CH:15][C:6]([S:1][CH2:2][CH2:3][OH:4])=[N:7]2)=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 15672-MercaptoethanolHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 126864152-Chloro-7-methoxyquinoxaline

Product 1

HCID 667462582-(7-Methoxy-quinoxalin-2-ylsulfanyl)-ethanolYield 99%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

2-Mercaptoethanol (2.5 g, 32.06 mmol, 1.2 eq) is added at room temperature to a stirred solution of 2-chloro-7-methoxy-quinoxaline (5.2 g, 26.72 mmol, 1.0 eq) in N,N-dimethylformamide (160 mL), followed by potassium carbonate (7.4 g, 53.44 mol, 2.0 eq). After 15 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×150 mL) and water (100 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: ethyl acetate:hexane, 1:2, v/v) to afford 2-(7-methoxy-quinoxalin-2-ylsulfanyl)-ethanol as a pale yellow solid (6.22 g, 99% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×150 mL) and water (100 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product that
  7. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-3fb749eee5e94620b0b5c2a69e436239
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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