Potassium Carbonate → 4-(3-Chloropyrazin-2-yloxy)-N-methoxy-N-methylbenzamide

HRID 2192004Notes

Reaction equation

HRID 2192004 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][CH:3]=1.[Cl:14][C:15]1[C:20](Cl)=[N:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:14][C:15]1[C:20]([O:1][C:2]2[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][CH:3]=2)=[N:19][CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 785752,3-DichloropyrazineHCID 113897574-Hydroxy-N-methoxy-N-methylbenzamide

Product 1

HCID 593513464-(3-Chloropyrazin-2-yloxy)-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-hydroxy-N-methoxy-N-methylbenzamide (6.50 g, 35.9 mmol), 2,3-dichloropyrazine (6.95 g, 46.6 mmol), and potassium carbonate (12.40 g, 90 mmol) in acetonitrile (70 mL) was heated at reflux in 18 h. The reaction mixture was cooled, concentrated, taken up in H2O, extracted with EtOAc, dried over MgSO4, concentrated and purified by ISCO (50% EtOAc/Hexanes) to give the titled compound. MS [M+1]: 294.1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux in 18 h
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. extractionextracted with EtOAc
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. custompurified by ISCO (50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-6842f96e27574693943d7c2dc0b50be2
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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