2,3-Dibromo-N-[(4-chlorophenyl)carbamoyl]propanamide → 1-(4-Chlorophenyl)-5-methylideneimidazolidine-2,4-dione

HRID 259166Notes

Reaction equation

HRID 259166 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12](=[O:17])[CH:13](Br)[CH2:14]Br)=[O:10])=[CH:4][CH:3]=1>C(O)(C)(C)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[CH2:14])[C:12](=[O:17])[NH:11][C:9]2=[O:10])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 214233172,3-Dibromo-N-[(4-chlorophenyl)carbamoyl]propanamide

Product 1

HCID 214056001-(4-Chlorophenyl)-5-methylideneimidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

25.0 g of the N-(4-chlorophenyl)-N'-(2,3-dibromopropionyl)-urea obtained in accordance with Example 4(b) are heated under reflux for 1 hour with 26.0 g of potassium tert.-butylate (90%) in 250 ml of tert.-butanol. The solvent is then distilled off under normal pressure and the residue is heated in vacuo for 20 minutes to 120° C. The reaction product is taken up with 500 ml of water at 60° C, precipitated with dilute acetic acid, filtered and dried. Yield: 12.0 g, m.p: 185° - 187° C.

Workup

  1. temperatureare heated
  2. distillationThe solvent is then distilled off under normal pressure
  3. temperaturethe residue is heated in vacuo for 20 minutes to 120° C
  4. customis taken up with 500 ml of water at 60° C
  5. customprecipitated with dilute acetic acid
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-06cda80c3ae647cfb4f0dac0f22c4e66
Source dataset
uspto-grants-1977_07
Patent number
US04036850

Reaction notes

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