Phenol → HCID 18964315, compound

HRID 2254539Notes

Reaction equation

HRID 2254539 reaction equation
C(N(CC)CC)C.Cl[CH:9]([C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])=[O:11].[C:27]1([OH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C>[CH3:23][C:22]([CH3:25])([CH3:24])[C:21](=[O:26])[CH:9]([O:33][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])=[O:11]

Participants

5

Reactant 3

HCID 996PhenolHCID 8471TriethylamineHCID 112507Pentanamide, 2-chloro-N-(2,4-dichlorophenyl)-4,4-dimethyl-3-oxo-

Product 1

HCID 18964315HCID 18964315, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Triethylamine (57.35 g, 566 mmol) was added to a stirred solution of N-[2-chloro-4,4,-dimethyl-3-oxopentanoyl]-2,4-dichloroaniline prepared as above (155.9 g, 483 mmol) and phenol (49.9 g, 530 mmol) in dry acetonitrile (1.3 L) under argon. After the addition had been completed, the mixture was heated at reflux for 7 hours. The reaction mixture was then cooled and the solvent was removed under reduced pressure. The residue was dissolved in methanol (300 mL) and allowed to stir at room temperature until crystallization began. After 2 hours, the mixture was cooled in an ice bath for a further 1 hour. The product was removed by filtration, washed with cold methanol, and dried to afford N-[4,4-dimethyl-3-oxo-2-phenoxypentanoyl]-2,4-dichloroaniline (99 g, 54% yield) as a white crystalline solid which melted at 112°-113.5° C. The structure of this compound was confirmed by mass spectroscopy and by 1H and 13C NMR spectroscopy.

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 7 hours
  4. temperatureThe reaction mixture was then cooled
  5. customthe solvent was removed under reduced pressure
  6. dissolutionThe residue was dissolved in methanol (300 mL)
  7. temperaturethe mixture was cooled in an ice bath for a further 1 hour
  8. customThe product was removed by filtration
  9. washwashed with cold methanol
  10. customdried

Sources & evidence

ORD record
ord-7e81a9948dd74372b1b63d8b536510b9
Source dataset
uspto-grants-1993_08
Patent number
US05236884

Reaction notes

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