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

HRID 345768

반응식

HRID 345768 반응식
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]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 702912,5-Cyclohexadiene-1,4-dione, 2,3,5-trimethyl-HCID 178418806HCID 178418806, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 63651,1-Dichloroethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-f8f076ed8eef4525bfae4655b36c182a
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05059598

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