1-Phenylimidazolidine-2,4-dione → HCID 21472164, compound

HRID 2294801Notes

Reaction equation

HRID 2294801 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:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>N1C=CC=CC=1>[O:14]([C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([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:24])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 5705761-Phenylimidazolidine-2,4-dioneHCID 110753032-Phenoxybenzoyl chloride

Product 1

HCID 21472164HCID 21472164, compoundYield 34.5%

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 700 mg (3.00 mmol) of 2-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 purified by column chromatography on silica gel (developing solvent: n-hexane/ethyl acetate) and subjected to crystallization from n-hexane/ethyl acetate to obtain 360 mg (yield: 32.8%) 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 purified by column chromatography on silica gel (developing solvent: n-hexane/ethyl acetate)
  7. customsubjected to crystallization from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-ab242725332140d9bbcd111e7f858171
Source dataset
uspto-grants-1997_11
Patent number
US05691335

Reaction notes

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