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

HRID 845292

反応式

HRID 845292 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[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[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[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[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 226912-Chloro-5-nitroanilineHCID 143035452-Methyl-1,5-diphenylpentane-1,3,5-trione

生成物 1

HCID 143036481-(2-chloro-5-nitrophenyl)-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 3.4 g (0.012 mole) of 2-methyl-1,5-diphenyl-1,3,5-pentanetrione, 10.4 g (0.060 mole) of 2-chloro-5-nitroaniline, 4.1 g (0.022 mole) of para-toluenesulfonic acid and 35.0 g of Molecular Sieves 5A, followed by refluxing for 2 hours. After cooling the reaction mixture, solid matter was removed from the reaction mixture, followed by 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, 1.9 g of 1-(2-chloro-5-nitrophenyl)-3-methyl- 2,6-diphenyl-4(1H)-pyridinone having a melting point of 277°-279° C. was obtained.

後処理

  1. temperatureby refluxing 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 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, 1.9 g of 1-(2-chloro-5-nitrophenyl)-3-methyl- 2,6-diphenyl-4(1H)-pyridinone having a melting point of 277°-279° C.
  12. customwas obtained

出典と根拠

ORDレコード
ord-08bcb19cabc64fe9a1ef037aa5a91841
出典データセット
uspto-grants-1988_07
特許番号
US04757081

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