Sodium Acetate → HCID 72277073, compound

HRID 568572Notes

Reaction equation

HRID 568572 reaction equation
[CH3:1][C:2]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.C([O-])(=O)C.[Na+].Cl.[CH3:31][O:32][NH2:33]>C(O)C>[CH3:1][C:2]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH:18]3[S:22][C:21](=[O:23])[NH:20][C:19]3=[O:24])=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[N:33][O:32][CH3:31]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 15591801HCID 15591801, compound

Product 1

HCID 72277073HCID 72277073, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-[[4-[(1-methyl-2-oxocyclohexyl)methoxy]phenyl]methyl]-2,4-thiazolidinedione (3 g), sodium acetate (0.78 g) and O-methylhydroxylamine hydrochloride (0.66 g) were suspended in ethanol (200 mL) and refluxed overnight. The reaction mixture was concentrated in vacuo and the residue dissolved in ethyl acetate and dried over MgSO4. Filtration and concentration left 3.25 g of yellow oil which was purified by high pressure liquid chromatography. The product, 2.21 g of yellow oil, was dissolved in ethanol (100 mL) and stirred overnight at room temperature with KOH (0.35 g). The solvent was removed using a rotary evaporator, ethyl acetate was added, and the product was dried over Na2SO4. After filtration and concentration, the product was dried overnight under vacuum at room temperature to give 1.79 g of thepotassium salt of the title compound as a white solid, which fuses at 135°-138° C.

Workup

  1. temperaturerefluxed overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationFiltration and concentration
  6. waitleft 3.25 g of yellow oil which
  7. customwas purified by high pressure liquid chromatography
  8. dissolutionThe product, 2.21 g of yellow oil, was dissolved in ethanol (100 mL)
  9. customThe solvent was removed
  10. customa rotary evaporator, ethyl acetate
  11. additionwas added
  12. dry with materialthe product was dried over Na2SO4
  13. filtrationAfter filtration and concentration
  14. customthe product was dried overnight under vacuum at room temperature

Sources & evidence

ORD record
ord-88fc67e81e98483e91c5a7ccec6b35c9
Source dataset
uspto-grants-1988_03
Patent number
US04728739

Reaction notes

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