Urea → Ethyl 2-amino-4-methyl-1,3-oxazole-5-carboxylate

HRID 70228

Reaction equation

HRID 70228 reaction equation
Cl[CH:2]([C:8]([CH3:10])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:11][C:12]([NH2:14])=[O:13]>CO>[NH2:14][C:12]1[O:13][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([CH3:10])[N:11]=1

Participants

4

Reactant 2

HCID 1176UreaHCID 11858Ethyl 2-chloroacetoacetate

Product 1

HCID 12753431Ethyl 2-amino-4-methyl-1,3-oxazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
66 °C

Procedure

Ethyl 2-chloroacetoacetate (8.0 mL, 59 mmol) was added to a mixture of urea (10.6 g, 176 mmol) in MeOH (40 mL), and the reaction mixture was heated to 66° C. overnight. Upon cooling to room temperature, the solids were collected by filtration and suspended in 1 N aqueous NaOH (50 mL). This was extracted with EtOAc (100 mL). The aqueous layer was brought to pH ˜11 with NaOH and was extracted with EtOAc (3×100 mL). The EtOAc extracts were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure. This gave 5.02 g (50%) of the title compound as a white solid. LC-MS: RT=5.1 min, [M+H]+=171.

Workup

  1. temperatureUpon cooling to room temperature
  2. filtrationthe solids were collected by filtration
  3. extractionThis was extracted with EtOAc (100 mL)
  4. extractionwas extracted with EtOAc (3×100 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8793415874c847e39dc0ac24a4afed71
Source dataset
uspto-grants-2014_09
Patent number
US08822472B2

Linked notes

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