Pentafluoroaniline → 3-methyl-1-(2,3,4,5,6-pentafluorophenyl)-2,6-diphenyl-4(1H)-pyridinone

HRID 845298

반응식

HRID 845298 반응식
[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[C:29]([F:30])=[C:28]([F:31])[C:27]([F:32])=[C:26]([F:33])[C:24]=1[NH2:25]>C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[C:11](=[O:21])[CH:12]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:25]([C:24]2[C:26]([F:33])=[C:27]([F:32])[C:28]([F:31])=[C:29]([F:30])[C:23]=2[F:22])[C:3]=1[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

참가 물질

4

반응물 2

HCID 13040PentafluoroanilineHCID 143035452-Methyl-1,5-diphenylpentane-1,3,5-trione

생성물 1

HCID 143036943-methyl-1-(2,3,4,5,6-pentafluorophenyl)-2,6-diphenyl-4(1H)-pyridinone수율 27.7%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

In 110 ml of xylene were dissolved 3.1 g (0.011 mole) of 2-methyl-1,5-diphenyl-1,3,5-pentanetrione, 20.0 g (0.11 mole) of 2,3,4,5,6-pentafluoroaniline, 3.1 g (0.016 mole) of paratoluenesulfonic acid and 22.0 g of Molecular Sieves 5A, followed by reflux for 1 hours. After cooling the reaction mixture, solid matter was removed by filtration and the filtrate was then concentrated. After 200 ml of chloroform was added, the resultant solution in chloroform was washed first with 50 ml of 10% hydrochloric acid and then with 50 ml of a 10% aqueous solution of sodium hydroxide. After washing the solution in chloroform 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 column chromatography (eluent: 50:1 mixed solvent of chloroform and methanol). The resulting crystals were recrystallized from a 1:1 mixed solvent of acetone and hexane, thereby affording 1.3 g of 3-methyl-1-(2,3,4,5,6-pentafluorophenyl)-2,6-diphenyl-4(1H)-pyridinone having a melting point of 192°-194° C.

후처리

  1. temperatureby reflux for 1 hours
  2. temperatureAfter cooling the reaction mixture, solid matter
  3. customwas removed by filtration
  4. concentrationthe filtrate was then concentrated
  5. additionAfter 200 ml of chloroform was added
  6. washthe resultant solution in chloroform was washed first with 50 ml of 10% hydrochloric acid
  7. washAfter washing the solution in chloroform further with water, it
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. customSubsequent to removal of the sodium sulfate
  10. distillationthe solvent was distilled off
  11. customThe resulting crystals were recrystallized from a 1:1 mixed solvent of acetone and hexane

출처 및 근거

ORD 기록
ord-4ef7abd484324b428735bd7ac7cba367
출처 데이터셋
uspto-grants-1988_07
특허 번호
US04757081

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