m-Anisoyl chloride → HCID 21472140, compound

HRID 2294797Notes

Reaction equation

HRID 2294797 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.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=[O:20]>N1C=CC=CC=1>[C:1]1([N:7]2[CH2:11][C:10](=[O:12])[N:9]([C:19](=[O:20])[C:18]3[CH:22]=[CH:23][CH:24]=[C:16]([O:15][CH3:14])[CH:17]=3)[C:8]2=[O:13])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 74374m-Anisoyl chlorideHCID 5705761-Phenylimidazolidine-2,4-dione

Product 1

HCID 21472140HCID 21472140, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a similar manner to Example 8, 580 mg (3.30 mmol) of 1-phenyl-imidazolidin-2,4-dione were reacted with560 mg (3.29 mmol) of 3-methoxybenzoyl 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 90 mg (yield: 10.2%) 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-8dfd2203be554ea786ba9e2c5a91a4f6
Source dataset
uspto-grants-1997_11
Patent number
US05691335

Reaction notes

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