Ethanol → HCID 178418578, compound

HRID 5201Notes

Reaction equation

HRID 5201 reaction equation
[C:1]([O-:7])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[Li+].[C:9]([NH:12][NH2:13])([NH2:11])=[NH:10].Cl.C(O)C>O>[C:9]([NH:12][N:13]=[C:3]([CH3:5])[CH2:2][C:1]([OH:7])=[O:6])(=[NH:10])[NH2:11]

Participants

5

Reactant 3

HCID 702EthanolHCID 27242463-oxobutanoic acid lithium saltHCID 178418668HCID 178418668, compound

Product 1

HCID 178418578HCID 178418578, compoundYield 54.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Lithium acetoacetate (0.655 g) in 2 ml water treated with 0.665 g aminoguanidine HCl in 1.33 ml water. The solution was heated to reflux over 30 minutes and then allowed to cool. Ethanol (10 ml) was added and the mixture was stored at -20° C. for 24 hrs., then at 4° C. for 24 hrs. The mixture was allowed to reach room temperature and filtered. The filtrate was concentrated to a paste and triturated with 5 ml ethanol. Filtration and washing with ethanol gave 0.522 g of the hydrazone as a microcrystalline powder, melting point 138.6°-140° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux over 30 minutes
  3. temperatureto cool
  4. wait, then at 4° C. for 24 hrs
  5. customto reach room temperature
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated to a paste
  8. customtriturated with 5 ml ethanol
  9. filtrationFiltration
  10. washwashing with ethanol

Sources & evidence

ORD record
ord-765eee938f5f4e1793095537f302f9ea
Source dataset
uspto-grants-1993_09
Patent number
US05243071

Reaction notes

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