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

HRID 845291

反応式

HRID 845291 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.[F:22][C:23]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:24]=1[NH2:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[F:22][C:23]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:24]=1[N:25]1[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][C:11](=[O:21])[C:2]([CH3:1])=[C:3]1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 796472,6-DifluoroanilineHCID 143035452-Methyl-1,5-diphenylpentane-1,3,5-trione

生成物 1

HCID 143036411-(2,6-difluorophenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone収率 18.7%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

実験手順

To 150 ml of xylene were added 2.8 g (0.010 mole) of 2-methyl-1,5-diphenyl-1,3,5-pentanetrione, 12.9 g (0.010 mole) of 2,6-difluoroaniline, 3.0 g (0.016 mole) of para-toluenesulfonic acid and 30.0 g of Molecular Sieves 5A, followed by refluxing the resulting mixture for 3 hours. After cooling the reaction mixture, solid matter was filtered off and the filtrate was washed successively with 50 ml of 10% hydrochloric acid, 50 ml of a 10% aqueous solution of sodium hydroxide and water. The filtrate 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 crystallized from a 2:1 mixed solvent of acetone and hexane to give 0.7 g of 1-(2,6-difluorophenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 219°-221° C.

後処理

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

出典と根拠

ORDレコード
ord-8f321758208b4194b5ef506faadd5911
出典データセット
uspto-grants-1988_07
特許番号
US04757081

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