Acetone → HCID 23650059, compound

HRID 2238574Notes

Reaction equation

HRID 2238574 reaction equation
[C:1]1([S:7]([OH:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[C:20](=[O:37])[N:21]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH:24]=1)#[N:12].CC(C)=O>C(O)(C)C>[C:1]1([S:7]([OH:10])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19]1[C:20](=[O:37])[N:21]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH:24]=1)#[N:12]

Participants

5

Reactant 3

HCID 180AcetoneHCID 7371Benzenesulfonic AcidHCID 9924495Perampanel

Product 1

HCID 23650059HCID 23650059, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

A benzenesulfonic acid aqueous solution (1 mL, containing 2.02 mmol benzenesulfonic acid) was added to a mixture of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one (506 mg, 1.40 mmol) and acetone (5 mL), which was then heated to reflux in an oil bath for complete dissolution. Isopropanol (20 mL) was added to the mixture, which was then stirred at 60° C. for 40 minutes and subsequently allowed to stand for 13 hours in an oil bath, the heating of which was stopped. This mixture was then allowed to stand at 5° C. for 2 hours followed by collecting the precipitated solid by filtration. The resultant precipitate was dried with aeration at 60° C. for 3 hours to provide 442 mg of the title compound as pale yellow crystals.

Workup

  1. temperaturewas then heated
  2. temperatureto reflux in an oil bath for complete dissolution
  3. waitto stand for 13 hours in an oil bath
  4. temperaturethe heating of which
  5. waitto stand at 5° C. for 2 hours
  6. customby collecting the precipitated solid
  7. filtrationby filtration
  8. dry with materialThe resultant precipitate was dried with aeration at 60° C. for 3 hours

Sources & evidence

ORD record
ord-b2e6b35226bc466691e9de8bdf68bf94
Source dataset
uspto-grants-2010_05
Patent number
US07718807B2

Reaction notes

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