1-Phenylimidazolidine-2,4-dione → HCID 21472142, compound

HRID 2294800Notes

Reaction equation

HRID 2294800 reaction equation
[C:1]1([N:7]2[CH2:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:14]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[O:14]([C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24]([N:9]1[C:10](=[O:12])[CH2:11][N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]1=[O:13])=[O:25])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 5705761-Phenylimidazolidine-2,4-dioneHCID 27603413-Phenoxybenzoyl chloride

Product 1

HCID 21472142HCID 21472142, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner to Example 8, 500 mg (2.80 mmol) of 1-phenyl-imidazolidin-2,4-dione were reacted with 600 mg (2.80 mmol) of 3-phenoxybenzoyl chloride. After completion of the reaction, pyridine was distilled off under reduced pressure, and the resultant residue was subjected to extraction with ethyl acetate. The organic layer was washed with dilute hydrochloric acid and with saturated saline. The thus-washed organic layer was dried over anhydrous magnesium sulfate, and the solvent was then distilled off. The resultant residue was subjected to crystallization from n-hexane/ethyl acetate to obtain 780 mg (yield: 69.9%) of the title compound.

Workup

  1. distillationwas distilled off under reduced pressure
  2. extractionthe resultant residue was subjected to extraction with ethyl acetate
  3. washThe organic layer was washed with dilute hydrochloric acid and with saturated saline
  4. dry with materialThe thus-washed organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was then distilled off
  6. customThe resultant residue was subjected to crystallization from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-7849b2c853e14d539afe42ec660a3810
Source dataset
uspto-grants-1997_11
Patent number
US05691335

Reaction notes

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