p-Toluenesulfonic acid → HCID 14303987, compound

HRID 845297Notes

Reaction equation

HRID 845297 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH2:9][C:10](=[O:21])[CH:11]([CH3:20])[C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.[F:23][C:24]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[C:25]=1[NH2:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:26]([C:25]2[C:24]([F:23])=[CH:30][CH:29]=[CH:28][C:27]=2[F:31])[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:11]([CH3:20])[C:10](=[O:21])[CH:9]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 796472,6-DifluoroanilineHCID 19847698HCID 19847698, compound

Product 1

HCID 14303987HCID 14303987, compoundYield 24.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In 200 ml of xylene were dissolved 6.3 g (0.020 mole) of 5-(2-chlorophenyl)-2-methyl-1-phenyl-1,3,5-pentanetrione, 20.0 g (0.155 mole) of 2,6-difluoroaniline, 4.6 g (0.024 mole) of para-toluenesulfonic acid and 50.0 g of Molecular Sieves 5A, followed by reflux for 8 hours. Solid matter was filtered off from the reaction mixture and 300 ml of chloroform was added to the filtrate. The mixture obtained was washed first with 50 ml of 10% hydrochloric acid and then with 50 ml of a 10% aqueous solution of sodium hydroxide. After washing the chloroform layer further with water, it was dried over anhydrous sodium sulfate. Subsequent to removal of the sodium solfate, the solvent was distilled off and the residue was subjected to column chromatography (eluent: ethyl acetate) to afford crystals. The crystals were recrystallized from a 2:1 mixed solvent of acetone and hexane, thereby yielding 2.0 g of 6-(2-chlorophenyl)-1-(2,6-difluorophenyl)-3-methyl-2-phenyl-4(1H)-pyridinone having a melting point of 213°-215° C.

Workup

  1. temperatureby reflux for 8 hours
  2. filtrationSolid matter was filtered off from the reaction mixture and 300 ml of chloroform
  3. additionwas added to the filtrate
  4. customThe mixture obtained
  5. washwas washed first with 50 ml of 10% hydrochloric acid
  6. washAfter washing the chloroform layer further with water, it
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customSubsequent to removal of the sodium solfate
  9. distillationthe solvent was distilled off
  10. customto afford crystals
  11. customThe crystals were recrystallized from a 2:1 mixed solvent of acetone and hexane

Sources & evidence

ORD record
ord-2cd978063bbe47d7868093119e49369f
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Reaction notes

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