Ethanol → HCID 178437617, compound

HRID 1075287Notes

Reaction equation

HRID 1075287 reaction equation
[N:1](=[C:3]([C:7](=[O:9])[CH3:8])[C:4](=O)[CH3:5])O.[NH2:10][CH:11]([CH2:16][CH3:17])C(OC)=O.C(O)C.[OH-].[Na+]>C(#N)C>[C:7]([C:3]1[NH:1][C:11]([CH2:16][CH3:17])=[N:10][C:4]=1[CH3:5])(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 1510132-Aminobutyric acid methyl esterHCID 178468373HCID 178468373, compound

Product 1

HCID 178437617HCID 178437617, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 4.99 g (0.039 moles) of 3-oximino-2,4-pentanedione dissolved in acetonitrile (40 ml) was added 4.59 ml (0.039 moles) of methyl 2-aminobutyrate. After stirring for two hours at room temperature, then at reflux for 2.5 h, the reaction mixture was cooled and treated with 15 ml of ethanol and 15 ml of 10% aqueous sodium hydroxide. The resulting mixture was refluxed for 3.8 h, cooled, then extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, then concentrated in vacuo to give 0.024 moles (62% yield) of 5-acetyl-2-ethyl-4-methylimidazole.

Workup

  1. temperatureat reflux for 2.5 h
  2. temperaturethe reaction mixture was cooled
  3. temperatureThe resulting mixture was refluxed for 3.8 h
  4. temperaturecooled
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c351ba9af31c4b829a8d17528942ed03
Source dataset
uspto-grants-1983_07
Patent number
US04395547

Reaction notes

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