Pyridine → 2,3,6-trimethyl-4-(1H-pyrazol-5-ylimino)cyclohexa-2,5-dien-1-one

HRID 345768

反応式

HRID 345768 の反応式
N1C=CC=CC=1.[CH3:7][C:8]1[C:9](=O)[CH:10]=[C:11]([CH3:16])[C:12](=[O:15])[C:13]=1[CH3:14].[NH2:18][C:19]1[CH:23]=[CH:22][NH:21][N:20]=1>ClC(Cl)C.[Ti](Cl)(Cl)(Cl)Cl>[CH3:14][C:13]1[C:12](=[O:15])[C:11]([CH3:16])=[CH:10][C:9](=[N:18][C:19]2[CH:23]=[CH:22][NH:21][N:20]=2)[C:8]=1[CH3:7]

参加物

6

反応物 3

HCID 1049PyridineHCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-HCID 178418806HCID 178418806、化合物

生成物 1

HCID 1784282552,3,6-trimethyl-4-(1H-pyrazol-5-ylimino)cyclohexa-2,5-dien-1-one収率 24.2%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 63651,1-Dichloroethane溶媒

実験手順

A 1.62 ml quantity of pyridine was dissolved in 60 ml of dichloroethane, and 0.55 ml of titanium tetrachloride was added thereto. The mixture was refluxed with heating for 15 minutes. Then, to the mixture were added 1.50 g of 2,3,5-trimethyl-1,4-benzoquinone and 0.83 g of 3-aminopyrazole, and the mixture was refluxed with heating for 2 hours. The reaction mixture was cooled to room temperature and filtered through a Celite pad and the insoluble materials were washed there with chloroform. The filtrate was concentrated, and the resulting crude product was purified by silica gel column chromatography (eluent: diethyl ether-hexane=1:1), giving 0.52 g of 2,3,6-trimethyl-4-(3-pyrazolylimino)-2,5-cyclohexadien-1-one (Compound 37a) as a yellow solid. Table 3 below shows the structure and properties of Compound 37a.

後処理

  1. temperatureThe mixture was refluxed
  2. temperaturewith heating for 15 minutes
  3. temperaturethe mixture was refluxed
  4. temperaturewith heating for 2 hours
  5. filtrationfiltered through a Celite pad
  6. washthe insoluble materials were washed there with chloroform
  7. concentrationThe filtrate was concentrated
  8. customthe resulting crude product was purified by silica gel column chromatography (eluent: diethyl ether-hexane=1:1)

出典と根拠

ORDレコード
ord-f8f076ed8eef4525bfae4655b36c182a
出典データセット
uspto-grants-1991_10
特許番号
US05059598

関連ノート

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