p-Toluenesulfonic acid → HCID 14304021, compound

HRID 2350976Notes

Reaction equation

HRID 2350976 reaction equation
[CH3:1][CH:2]([C:11](=[O:22])[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=1)=O)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[F:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[F:23][C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[N:26]1[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[CH:16]=2)=[CH:12][C:11](=[O:22])[C:2]([CH3:1])=[C:3]1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 95842-FluoroanilineHCID 19847701HCID 19847701, compound

Product 1

HCID 14304021HCID 14304021, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

To 30 ml of xylene were added 2.0 g (0.0068 mole) of 2-methyl-5-(3-methylphenyl)-1-phenyl-1,3,5-pentanetrione, 7.6 g (0.068 mole) of 2-fluoroaniline, 2.0 g (0.012 mole) of para-toluenesulfonic acid and 14.0 g of Molecular Sieves 5A, followed by refluxing the resulting mixture for 1 hour. After cooling the reaction mixture, solid matter was filtered off and the filtrate was mixed with 100 ml of chloroform and then washed successively with 50 ml of 10% hydrochloric acid, 50 ml of a 10% aqueous solution of sodium hyroxide and water. The filtrate was then dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off and the residue was crystallized from a 1:3 mixed solvent of chloroform and hexane to give 1.3 g of 1-(2-fluorophenyl)-3-methyl-6-(3-methylphenyl)-2-phenyl-4-(1H)-pyridinone having a melting point of 211°-214° C.

Workup

  1. temperatureby refluxing the resulting mixture for 1 hour
  2. temperatureAfter cooling the reaction mixture, solid matter
  3. filtrationwas filtered off
  4. additionthe filtrate was mixed with 100 ml of chloroform
  5. washwashed successively with 50 ml of 10% hydrochloric acid, 50 ml of a 10% aqueous solution of sodium hyroxide and water
  6. dry with materialThe filtrate was then dried over anhydrous sodium sulfate
  7. customSubsequent to removal of the sodium sulfate
  8. distillationthe solvent was distilled off
  9. customthe residue was crystallized from a 1:3 mixed solvent of chloroform and hexane

Sources & evidence

ORD record
ord-7b79c25080bf4b1db8c3dfaebcf2c420
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

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