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

HRID 2350948

反応式

HRID 2350948 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3cb7d9adc1654650ae6197efa020bb29
出典データセット
uspto-grants-1989_10
特許番号
US04871751

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