Acetamide → Ethyl 2,4-dimethyl-1,3-oxazole-5-carboxylate

HRID 1624219Notes

Reaction equation

HRID 1624219 reaction equation
[C:1]([NH2:4])(=[O:3])[CH3:2].[CH2:5]([O:7][C:8](=[O:14])[CH2:9][C:10]([CH2:12]Cl)=O)[CH3:6].C(=O)([O-])O.[Na+].Cl>C(O)(=O)C>[CH3:2][C:1]1[O:3][C:9]([C:8]([O:7][CH2:5][CH3:6])=[O:14])=[C:10]([CH3:12])[N:4]=1

Participants

6

Reactant 4

HCID 178AcetamideHCID 313Hydrochloric AcidHCID 69484Ethyl 4-chloroacetoacetateHCID 516892Sodium Bicarbonate

Product 1

HCID 315151Ethyl 2,4-dimethyl-1,3-oxazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

800 mmol of acetoamide and 400 mmol of ethylchloroaceto acetate were dissolved into 146 g of anhydrous acetic acid. Reaction was carried out for 10 hours at 130° C. The reacted liquid was alkalized with saturated sodium hydrogen carbonate and then the product was extracted into an organic phase using ethyl acetate. The organic phase was dried under sodium sulfate and then the solvent was evaporated out, obtaining a black liquid. To this black liquid 6N hydrochloric acid aqueous solution was added to make it alkaline. Then the product was extracted into organic phase using ethyl acetate. The thus obtained solid substance was dissolved in hexane. Insoluble matter was eliminated and solvent was evaporated out, obtaining ethyl 2,4-dimethyl-1,3-oxazole-5-carboxylate, an yellowish white solid (yield: 30%).

Workup

  1. customReaction
  2. extractionthe product was extracted into an organic phase
  3. customThe organic phase was dried under sodium sulfate
  4. customthe solvent was evaporated out
  5. customobtaining a black liquid
  6. extractionThen the product was extracted into organic phase
  7. dissolutionThe thus obtained solid substance was dissolved in hexane
  8. customsolvent was evaporated out

Sources & evidence

ORD record
ord-bfe287ac4b3b45a5ae023297950183de
Source dataset
uspto-grants-2014_07
Patent number
US08779086B2

Reaction notes

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