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

HRID 2350951

反応式

HRID 2350951 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.[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-92581976988c440ea0569d9240c742fd
出典データセット
uspto-grants-1989_10
特許番号
US04871751

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