Sodium Acetate → HCID 24828929, compound

HRID 859183Notes

Reaction equation

HRID 859183 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5](=[N:17][NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])[C:6](=[O:16])[CH:7](Br)[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH3:2].C([O-])(=O)C.[Na+]>CO.C1CCCCC1>[CH2:1]([O:3][C:4]([C:5]1[C:6]([OH:16])=[C:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[N:17]=1)=[O:26])[CH3:2]

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 178472846HCID 178472846, compound

Product 1

HCID 24828929HCID 24828929, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8078CyclohexaneSolvent

Procedure

A mixture of 4-bromo4-(4-chloro-phenyl)-2-[(2-chloro-phenyl)-hydrazono]-3-oxo-butyric acid ethyl ester (12.1 g, 26 mmol) and sodium acetate (10.8 g, 130 mmol) in methanol (100 ml) was heated at reflux for 4 hours, cooled, concentrated in vacuo and the residue partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4) and concentrated in vacuo to afford a solid. A slurry of this material in cyclohexane was heated to reflux and allowed to stir at ambient temperature for 2 hours, and filtered to afford the title compound (I-1d) as a yellow solid (I-1d), 6.5 g.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customthe residue partitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto afford a solid
  10. temperatureto reflux
  11. filtrationfiltered

Sources & evidence

ORD record
ord-026fa372fac247a7924b5b40ed071121
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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