Potassium cyanate → 2,3-Dihydro-2-oxo-4,N,N-trimethyl-1H-imidazole-5-carboxamide

HRID 359704Notes

Reaction equation

HRID 359704 reaction equation
[CH3:1][N:2]([CH3:11])[C:3](=[O:10])[C:4](=[N:8]O)[C:5](=O)[CH3:6].[H][H].[O-:14][C:15]#[N:16].[K+]>C(O)C.Cl.O>[O:14]=[C:15]1[NH:16][C:5]([CH3:6])=[C:4]([C:3]([N:2]([CH3:11])[CH3:1])=[O:10])[NH:8]1

Participants

7

Reactant 3

HCID 11378442Potassium cyanateHCID 178418361HCID 178418361, compoundHCID 178468379HCID 178468379, compound

Product 1

HCID 128502882,3-Dihydro-2-oxo-4,N,N-trimethyl-1H-imidazole-5-carboxamide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 15.8 g (0.1 mol) of N,N-dimethyl-2-(hydroxyimino)-3-oxobutanamide in 400 ml of ethanol and 100 ml of 2N hydrochloric acid over 2 g of catalyst (5% palladium on charcoal) is hydrogenated in a Paar shaker until 1 molar equivalent of hydrogen is taken up (3-5 hours). The catalyst is removed by filtration. A solution of 16.2 g (0.2 mol) of potassium cyanate in 80 ml of water is added, the solution is refluxed for 1 hour and concentrated until the product crystallizes. Recrystallization from 50% aqueous ethanol gives the title compound, m.p. 244°-246° C. (dec).

Workup

  1. custom(3-5 hours)
  2. customThe catalyst is removed by filtration
  3. temperaturethe solution is refluxed for 1 hour
  4. concentrationconcentrated until the product
  5. customcrystallizes
  6. customRecrystallization from 50% aqueous ethanol

Sources & evidence

ORD record
ord-ea34432a812544cba5f70cb2d8c99279
Source dataset
uspto-grants-1991_03
Patent number
US05002961

Reaction notes

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