Urea → HCID 12993976, compound

HRID 351804Notes

Reaction equation

HRID 351804 reaction equation
Cl[CH:2]([C:7]([CH3:9])=O)[C:3]([O:5][CH3:6])=[O:4].[NH2:10][C:11]([NH2:13])=[O:12]>CO>[NH2:13][C:11]1[O:12][C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:7]([CH3:9])[N:10]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 107332Methyl 2-chloroacetoacetate

Product 1

HCID 12993976HCID 12993976, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

150 g of methyl 2-chloroacetoacetate and 180 g of urea were dissolved in 600 ml of methanol and refluxed for 36 hours. After cooling, the deposited crystals were filtered, suspended in 2N sodium hydroxide solution and extracted with ethyl acetate. After washing with water and drying with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was recrystallized from acetonitrile to obtain 10 g of 2-amino-5-methoxycarbonyl-4-methyloxazole. mp. 199-201° C. (point of decomposition).

Workup

  1. temperaturerefluxed for 36 hours
  2. temperatureAfter cooling
  3. filtrationthe deposited crystals were filtered
  4. extractionextracted with ethyl acetate
  5. washAfter washing with water
  6. dry with materialdrying with anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-ee12fd2bb143469fa9590fe449d9949b
Source dataset
uspto-grants-2004_06
Patent number
US06743814B2

Reaction notes

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