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

HRID 2350951

반응식

HRID 2350951 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.[Cl:22][C:23]1[C:29]([CH3:30])=[C:28]([Cl:31])[CH:27]=[CH:26][C:24]=1[NH2:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1>[Cl:22][C:23]1[C:29]([CH3:30])=[C:28]([Cl:31])[CH:27]=[CH:26][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

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 882822,4-Dichloro-m-toluidineHCID 143035452-Methyl-1,5-diphenylpentane-1,3,5-trione

생성물 1

HCID 143036882,4-dichloro-3-methylphenyl-3-methyl-2,6-diphenyl-4(1H)-pyridinone

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

실험 절차

In 170 ml of chlorobenzene were dissolved 3.4 g (0.012 mole) of 2-methyl-1,5-diphenyl-1,3,5-pentanetrione and 10.6 g (0.06 mole) of 2,4-dichloro-3-methylaniline, followed by further addition of 4.1 g (0.022 mole) of para-toluenesulfonic acid and 35.0 g of Molecular Sieves 5A to the solution. After heating the reaction mixture under reflux for 2 hours, solid matter was removed from the reaction mixture, followed by an addition of 200 ml of chloroform. The resultant mixture was washed first with 100 ml of 10% hydrochloric acid and then with 100 ml of a 10% aqueous solution of sodium hydroxide. The mixture was washed further with water and was then dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off and the residue was purified by 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, 0.7 g of 1-(2,4-dichloro-3-methylphenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 237°-238° C. was obtained.

후처리

  1. temperatureAfter heating the reaction mixture
  2. temperatureunder reflux for 2 hours
  3. customsolid matter was removed from the reaction mixture
  4. additionfollowed by an addition of 200 ml of chloroform
  5. washThe resultant mixture was washed first with 100 ml of 10% hydrochloric acid
  6. washThe mixture was washed further with water
  7. dry with materialwas then dried over anhydrous sodium sulfate
  8. customSubsequent to removal of the sodium sulfate
  9. distillationthe solvent was distilled off
  10. customthe residue was purified by chromatography on a silica gel column (eluent: ethyl acetate)
  11. customUpon recrystallization of the resultant crystals from a 2:1 mixed solvent of acetone and hexane, 0.7 g of 1-(2,4-dichloro-3-methylphenyl)-3-methyl-2,6-diphenyl-4(1H)-pyridinone having a melting point of 237°-238° C.
  12. customwas obtained

출처 및 근거

ORD 기록
ord-92581976988c440ea0569d9240c742fd
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04871751

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