Urea → Ethyl 2-amino-1,3-oxazole-4-carboxylate

HRID 1716855Notes

Reaction equation

HRID 1716855 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:10][C:11]([NH2:13])=[O:12]>CCO>[NH2:13][C:11]1[O:12][CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:10]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 66144Ethyl bromopyruvate

Product 1

HCID 319549Ethyl 2-amino-1,3-oxazole-4-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of ethyl bromopyruvate (50.2 g, 257.2 mmol) in EtOH was treated with urea (23.2 g, 385.8 mmol) refluxed overnight and concentrated under reduced pressure. The resultant residue was dissolved in EtOAC and water. The layers were separated and the aqueous layer washed with EtOAC. The combined organic layers were washed successively with saturated sodium chloride, dried over Mg2SO4 and concentrated under reduced pressure to give the title product in 85% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 157.1 (MH+).

Workup

  1. temperaturerefluxed overnight
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resultant residue was dissolved in EtOAC and water
  4. customThe layers were separated
  5. washthe aqueous layer washed with EtOAC
  6. washThe combined organic layers were washed successively with saturated sodium chloride
  7. dry with materialdried over Mg2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-da1cd99ffa3a4126abc1554071423f3f
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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