Potassium Carbonate → HCID 54506832, compound

HRID 1458585Notes

Reaction equation

HRID 1458585 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[C:9]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[N:14]=[C:13]([O:19][CH3:20])[C:12]([O:21][CH3:22])=[N:11]2.Br[CH2:29][C:30]([O:32][CH3:33])=[O:31]>CC(C)=O.C(OCC)(=O)C>[Cl:7][C:8]1[C:9]([N:23]([CH2:29][C:30]([O:32][CH3:33])=[O:31])[S:24]([CH3:27])(=[O:26])=[O:25])=[C:10]2[C:15](=[CH:16][C:17]=1[Cl:18])[N:14]=[C:13]([O:19][CH3:20])[C:12]([O:21][CH3:22])=[N:11]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 54321377HCID 54321377, compound

Product 1

HCID 54506832HCID 54506832, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Anhydrous potassium carbonate (1.60 g, 11.2 mmol) was added to a suspension of N-(6,7-dichloro-2,3-dimethoxyquinoxalin-5-yl)-methanesulphonamide (see Preparation 3, 3.0 g, 9.4 mmol) in acetone (70 ml) with stirring. The mixture was heated at reflux for 15 minutes, cooled, and methyl bromoacetate (1.8 ml, 18.7 mmol) was added. The mixture was then heated at reflux for 2 h, cooled, diluted with ethyl acetate (300 ml) and washed with water (2×100 ml). The organic phase was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (gradient elution with hexane/ethyl acetate) to give the title compound as a white solid (3.177 g, 80%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 15 minutes
  3. temperaturecooled
  4. temperatureThe mixture was then heated
  5. temperatureat reflux for 2 h
  6. temperaturecooled
  7. washwashed with water (2×100 ml)
  8. dry with materialThe organic phase was dried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography (gradient elution with hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c75265b01a244a9a8cc00fa35aee6f7e
Source dataset
uspto-grants-1998_12
Patent number
US05852016

Reaction notes

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