2-Chlorobenzoyl chloride → 3-(2-Chlorobenzoyl)-1-phenyl-imidazolidin-2,4-dione

HRID 2294796

Reaction equation

HRID 2294796 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.[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](Cl)=[O:18]>N1C=CC=CC=1>[Cl:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([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:18]

Participants

4

Reactant 2

HCID 691102-Chlorobenzoyl chlorideHCID 5705761-Phenylimidazolidine-2,4-dione

Product 1

HCID 214721873-(2-Chlorobenzoyl)-1-phenyl-imidazolidin-2,4-dioneYield 13%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner to Example 8, 560 mg (3.18 mmol) of 1-phenyl-imidazolidin-2,4-dione were reacted with 560 mg (3.22 mmol) of 2-chlorobenzoyl 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: methylene chloride) and subjected to crystallization from n-hexane/ethyl acetate to obtain 130 mg (yield: 12.9%) 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 purified by column chromatography on silica gel (developing solvent: methylene chloride)
  7. customsubjected to crystallization from n-hexane/ethyl acetate

Sources & evidence

ORD record
ord-c03abd8f4def4823a4020e1ca7a9b90b
Source dataset
uspto-grants-1997_11
Patent number
US05691335

Linked notes

Loading…