2,3-Dibromo-N-(phenylcarbamoyl)propanamide → 5-Methylidene-1-phenylimidazolidine-2,4-dione

HRID 259162Notes

Reaction equation

HRID 259162 reaction equation
[C:1]1([NH:7][C:8]([NH:10][C:11](=[O:16])[CH:12](Br)[CH2:13]Br)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(C)(C)C.O>[C:1]1([N:7]2[C:12](=[CH2:13])[C:11](=[O:16])[NH:10][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 203185402,3-Dibromo-N-(phenylcarbamoyl)propanamide

Product 1

HCID 214055985-Methylidene-1-phenylimidazolidine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

20.0 g of the N-phenyl-N'-(2,3-dibromopropionyl)-urea prepared in accordance with Example 1(b) are suspended in 200 ml of tert.-butanol, 23 g of potassium tert.-butylate (90%) are introduced into the resulting suspension and the mixture is heated under reflux for 1 hour. The solvent is then distilled off under normal pressure and the residue is heated in vacuo for 20 minutes to 120° C. The white crystalline powder obtained is dissolved in 400 ml of water at 60° C. and the solution is filtered and adjusted to pH 1 with dilute hydrochloric acid. The precipitated imidazolidine derivative is filtered off, washed and dried. Yield: 9.0g m.p: 168° - 170° C. (from methanol)

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 1 hour
  3. distillationThe solvent is then distilled off under normal pressure
  4. temperaturethe residue is heated in vacuo for 20 minutes to 120° C
  5. customThe white crystalline powder obtained
  6. filtrationthe solution is filtered
  7. filtrationThe precipitated imidazolidine derivative is filtered off
  8. washwashed
  9. customdried

Sources & evidence

ORD record
ord-b915fc65c1fd47fe80ade819353fff11
Source dataset
uspto-grants-1977_07
Patent number
US04036850

Reaction notes

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