p-Toluenesulfonic acid → HCID 14303913, compound

HRID 2350975Notes

Reaction equation

HRID 2350975 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([CH3:22])[C:11](=[O:21])[CH2:12][C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=O)=[CH:5][CH:4]=1.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH:30]=[C:31]([O:33][CH3:34])[CH:32]=1)[NH2:29].[C:35]1([CH3:45])[CH:40]=[CH:39][C:38]([S:41]([OH:44])(=[O:43])=[O:42])=[CH:37][CH:36]=1>ClC1C=CC=CC=1>[C:35]1([CH3:45])[CH:36]=[CH:37][C:38]([S:41]([OH:44])(=[O:42])=[O:43])=[CH:39][CH:40]=1.[CH3:34][O:33][C:31]1[CH:30]=[C:28]([N:29]2[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:12][C:11](=[O:21])[C:10]([CH3:22])=[C:9]2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:27]=[C:26]([O:25][CH3:24])[CH:32]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 663013,5-DimethoxyanilineHCID 19847704HCID 19847704, compound

Product 1

HCID 14303913HCID 14303913, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To 200 ml of chlorobenzene were added 3.1 g (0.01 mole) of 1-(4-methoxyphenyl)-2-methyl-5-phenyl-1,3,5-pentanetrione, 2.3 g (1.5 mole) of 3,5-dimethoxyaniline, 2.9 g (0.015 mole) of para-toluenesulfonic acid and 10 g of Molecular Sieves 5A, followed by refluxing the resulting mixture for 2 hours. After cooling the reaction mixture, solid matter was removed from the reaction mixture, followed by addition of 500 ml of chloroform thereto. The organic layer was washed first with 200 ml of 10% hydrochloric acid and then with water. The organic layer was then dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate by filtration, the solvent was distilled off and the residue was subjected to chromatography on a silica gel column (eluent: ethyl acetate). Upon washing the resultant crystals with ethyl acetate, 3.3 g of 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)-3-methyl-6-phenyl-4(1H)-pyridinone p-toluenesulfonate having a melting point of 202°-204° C. was obtained.

Workup

  1. temperatureby refluxing the resulting mixture for 2 hours
  2. temperatureAfter cooling the reaction mixture, solid matter
  3. customwas removed from the reaction mixture
  4. additionfollowed by addition of 500 ml of chloroform
  5. washThe organic layer was washed first with 200 ml of 10% hydrochloric acid
  6. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  7. customSubsequent to removal of the sodium sulfate
  8. filtrationby filtration
  9. distillationthe solvent was distilled off
  10. washUpon washing the resultant crystals with ethyl acetate, 3.3 g of 1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)-3-methyl-6-phenyl-4(1H)-pyridinone p-toluenesulfonate having a melting point of 202°-204° C.
  11. customwas obtained

Sources & evidence

ORD record
ord-8bcc57d2a7ae4e0c80b63c167cd71b8c
Source dataset
uspto-grants-1989_10
Patent number
US04871751

Reaction notes

Loading…