HCID 15677249, compound → HCID 178440053, compound

HRID 1462218Notes

Reaction equation

HRID 1462218 reaction equation
[N:1](=[C:3]([C:7](=[O:9])[CH3:8])[C:4](=O)[CH3:5])O.C[NH:11][CH:12](C(O)=O)[CH2:13][CH2:14][CH3:15]>C(#N)C>[C:7]([C:3]1[NH:1][C:12]([CH2:13][CH2:14][CH3:15])=[N:11][C:4]=1[CH3:5])(=[O:9])[CH3:8]

Participants

4

Reactant 2

HCID 15677249HCID 15677249, compoundHCID 178468373HCID 178468373, compound

Product 1

HCID 178440053HCID 178440053, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 40 g (0.31 moles) of 3-oximino-2,4-pentanedione dissolved in 297 ml of acetonitrile was added 40.64 g (0.31 moles) of methyl d,1-norvaline. The reaction mixture was refluxed 21.2 h under nitrogen, cooled, then concentrated in vacuo. The resulting oil was dissolved in 50 ml of ethanol and 140 ml of 10% aqueous sodium hydroxide. After 4 h of reflux, the cooled mixture was extracted with ethyl acetate (900 ml total) and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo afforded 0.16 moles (51% yield) of 5-acetyl-4-methyl-2-propylimidazole.

Workup

  1. temperatureThe reaction mixture was refluxed 21.2 h under nitrogen
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting oil was dissolved in 50 ml of ethanol
  5. temperatureAfter 4 h of reflux
  6. extractionthe cooled mixture was extracted with ethyl acetate (900 ml total)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-742f854ecb9944b6b84046f18d861a41
Source dataset
uspto-grants-1984_07
Patent number
US04459413

Reaction notes

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