Imidazole → 6,7Dichloro-2,3-dimethoxy-5-(1-imidazol-1-ylethyl)quinoxaline

HRID 1957110Notes

Reaction equation

HRID 1957110 reaction equation
Cl[CH:2]([C:4]1[C:13]([Cl:14])=[C:12]([Cl:15])[CH:11]=[C:10]2[C:5]=1[N:6]=[C:7]([O:18][CH3:19])[C:8]([O:16][CH3:17])=[N:9]2)[CH3:3].[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:14][C:13]1[C:4]([CH:2]([N:20]2[CH:24]=[CH:23][N:22]=[CH:21]2)[CH3:3])=[C:5]2[C:10](=[CH:11][C:12]=1[Cl:15])[N:9]=[C:8]([O:16][CH3:17])[C:7]([O:18][CH3:19])=[N:6]2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 190688705-(1-Chloroethyl)-6,7-dichloro-2,3-dimethoxyquinoxaline

Product 1

HCID 190689056,7Dichloro-2,3-dimethoxy-5-(1-imidazol-1-ylethyl)quinoxalineYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-(1-chloroethyl)-6,7dichloro-2,3-dimethoxyquinoxaline (95 mg, 0.295 mmol), imidazole (22 mg, 0.325 mmol), anhydrous potassium carbonate (45 mg, 0.325 mmol) in dry dimethylformamide (10 mL) was heated under nitrogen at 100° C. for 6 hours, cooled, and partitioned between brine and three portions of ethyl acetate. The combined organic solutions were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography (gradient elution with dichloromethane:mehanol) to give 6,7dichloro-2,3-dimethoxy-5-(1-imidazol-1-ylethyl)quinoxaline (60 mg, 58%); as a yellow solid.

Workup

  1. temperaturecooled
  2. custompartitioned between brine and three portions of ethyl acetate
  3. dry with materialThe combined organic solutions were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (gradient elution with dichloromethane:mehanol)

Sources & evidence

ORD record
ord-3192c6fc49e14bf090c3436935f87c28
Source dataset
uspto-grants-1998_07
Patent number
US05783572

Reaction notes

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