p-Toluenesulfonic acid → HCID 14303862, compound

HRID 845295Notes

Reaction equation

HRID 845295 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[CH:9]([CH3:21])[C:10](=[O:20])[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=O.[CH3:23][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>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:26]([C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[CH3:23])[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][C:10](=[O:20])[C:9]=1[CH3:21]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7242O-ToluidineHCID 19847705HCID 19847705, compound

Product 1

HCID 14303862HCID 14303862, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

In 500 ml of xylene were dissolved 37.7 g (0.012 mole) of 1-(2-chlorophenyl)-2-methyl-5-phenyl-1,3,5-pentanetrione, 38.6 g (0.36 mole) of 2-methylaniline, 22.8 g (0.12 mole) of para-toluenesulfonic acid and 30 g of Molecular Sieves 5A, followed by refluxing the resulting mixture for 8 hours. After cooling, solid matter was filtered off and the organic layer was washed first with 100 ml of 10% hydrochloric acid and then with 100 ml of a 10% aqueous solution of sodium hydroxide. After washing the organic layer further with water, it was dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off and the residue was subjected to chromatography on a silica gel column (eluent: ethyl acetate). As result, two atrop-isomers of 2-(2-chlorophenyl)-3-methyl-1-(2-methylphenyl)-6-phenyl-4(1H)-pyridinone, namely, Compound 338 and Compound 339 were obtained in yields of 1.2 g and 8.0 g, respectively. Their melting points were 227°-229° C. and 222°-225° C., respectively.

Workup

  1. temperatureby refluxing the resulting mixture for 8 hours
  2. temperatureAfter cooling
  3. filtrationsolid matter was filtered off
  4. washthe organic layer was washed first with 100 ml of 10% hydrochloric acid
  5. washAfter washing the organic layer further with water, it
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. customSubsequent to removal of the sodium sulfate
  8. distillationthe solvent was distilled off
  9. customAs result

Sources & evidence

ORD record
ord-7a80f4d569984ff4b1fdfcce4bfaf54c
Source dataset
uspto-grants-1988_07
Patent number
US04757081

Reaction notes

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