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p-Toluenesulfonic acid → 1-(3,5-dimethoxyphenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone

HRID 845290
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 845290
[CH3:1][CH:2]([C:11](=[O:21])[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:28]=[C:29]([O:31][CH3:32])[CH:30]=1)[NH2:27].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1>[CH3:32][O:31][C:29]1[CH:28]=[C:26]([N:27]2[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:12][C:11](=[O:21])[C:2]([CH3:1])=[C:3]2[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:25]=[C:24]([O:23][CH3:22])[CH:30]=1
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Komponenten

5

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 663013,5-DimethoxyanilineHCID 143035452-Methyl-1,5-diphenylpentane-1,3,5-trione

Produkt 1

HCID 143035461-(3,5-dimethoxyphenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

To 170 ml of chlorobenzene were added 4.2 g (0.015 mole) of 2-methyl-1,5-diphenyl-1,3,5-pentanetrione, 11.5 g (0.075 mole) of 3,5-dimethoxyaniline, 5.2 g (0.027 mole) of para-toluenesulfonic acid and 35.0 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 200 ml of chloroform thereto. The organic layer was washed first with 200 ml of 10% hydrochloric acid and then with 200 ml of a 10% aqueous solution of sodium hydroxide. The organic layer was washed further with water and 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 recrystallization of the resultant crystals from a 2:1 mixed solvent of acetone and hexane, 2.0 g of 1-(3,5-dimethoxyphenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 232°-236° C. was obtained.

Aufarbeitung

  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 200 ml of chloroform
  5. washThe organic layer was washed first with 200 ml of 10% hydrochloric acid
  6. washThe organic layer was washed further with water
  7. dry with materialwas then dried over anhydrous sodium sulfate
  8. customSubsequent to removal of the sodium sulfate
  9. filtrationby filtration
  10. distillationthe solvent was distilled off
  11. customUpon recrystallization of the resultant crystals from a 2:1 mixed solvent of acetone and hexane, 2.0 g of 1-(3,5-dimethoxyphenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 232°-236° C.
  12. customwas obtained

Quellen und Nachweise

ORD-Eintrag
ord-55ab7280e130463098fd4a88ed231ceb
Quelldatensatz
uspto-grants-1988_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04757081

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