Hydrochloric Acid → methyl 5-methyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylate

HRID 1348955Notes

Reaction equation

HRID 1348955 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH:4]([NH2:8])[C:5](=O)[CH3:6].[O:10]([C:12]#[N:13])[K].Cl>C(O)C>[CH3:1][O:2][C:3]([C:4]1[NH:8][C:12](=[O:10])[NH:13][C:5]=1[CH3:6])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12052398Methyl 2-amino-3-oxobutanoateHCID 178418250HCID 178418250, compound

Product 1

HCID 14677122methyl 5-methyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylateYield 96.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-amino-3-oxo-butyric acid methyl ester (100 mmol) (Lida, H. et al. Synthetic Communication, 1973, 3, 225–230) in 150 mL of ethanol was added KOCN (16.2 g, 200 mmol). The mixture was heated at 80° C. for 2 h. The solution was acidified with 2 N HCl and concentrated to half of the volume in vacuo. The product precipitated out upon cooling. Filtration, followed by washing with water, provided 5-methyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid methyl ester 4a (15 g, >95%). MS (ESI+) (M+1)=157.

Workup

  1. concentrationconcentrated to half of the volume in vacuo
  2. customThe product precipitated out
  3. temperatureupon cooling
  4. filtrationFiltration
  5. washby washing with water

Sources & evidence

ORD record
ord-5cf87931236647e49fa7510a926a58ad
Source dataset
uspto-grants-2007_05
Patent number
US07211671B2

Reaction notes

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