Urea → (2,5-Dioxo-imidazolidin-4-ylidene)-ethoxy-acetic acid ethyl ester

HRID 628973Notes

Reaction equation

HRID 628973 reaction equation
[CH2:1]([O:3][CH:4]([C:10](=O)[C:11]([O:13]CC)=O)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].[NH2:17][C:18]([NH2:20])=[O:19].Cl.CC(O)=O>>[CH2:8]([O:7][C:5](=[O:6])[C:4](=[C:10]1[C:11](=[O:13])[NH:20][C:18](=[O:19])[NH:17]1)[O:3][CH2:1][CH3:2])[CH3:9]

Participants

4

Reactant 3

HCID 1176UreaHCID 111389942-Ethoxy-3-oxo-succinic acid diethyl esterHCID 22641269Acetate-hydrochloric acid

Product 1

HCID 67295487(2,5-Dioxo-imidazolidin-4-ylidene)-ethoxy-acetic acid ethyl ester

Procedure

A mixture of diethyl 2-ethoxy-3-oxo-succinate (55.86 g, 1 eq) and urea (14.41 g, 1 eq.) was refluxed for 2.5 h in 1 M HCl—AcOH (1200 ml, 5 eq.) and allowed to become cool. The cooled mixture was evaporated to dryness. The residues were dissolved in MeOH, heated aside for crystallization. After crystallization, the precipitates were filtered to give a product which was an off-white solid (15.11 g, 27.5%).

Workup

  1. temperatureto become cool
  2. customThe cooled mixture was evaporated to dryness
  3. dissolutionThe residues were dissolved in MeOH
  4. temperatureheated aside for crystallization
  5. customAfter crystallization
  6. filtrationthe precipitates were filtered
  7. customto give a product which

Sources & evidence

ORD record
ord-1cfb294b25b94352b171941aab719456
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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