Hexafluoroacetylacetone → HCID 23036563, 화합물

HRID 1709696노트

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HRID 1709696 반응식
[F:1][C:2]([F:13])([F:12])[C:3](=O)[CH2:4][C:5](=O)[C:6]([F:9])([F:8])[F:7].[Cl:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[C:17]([Cl:24])[C:16]=1[NH:25][NH2:26]>CO>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([C:6]([F:9])([F:8])[F:7])[N:25]([C:16]2[C:17]([Cl:24])=[CH:18][C:19]([N+:21]([O-:23])=[O:22])=[CH:20][C:15]=2[Cl:14])[N:26]=1

참가 물질

4

반응물 2

HCID 73706HexafluoroacetylacetoneHCID 21179877(2,6-Dichloro-4-nitrophenyl)hydrazine

생성물 1

HCID 23036563HCID 23036563, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

1,1,1,5,5,5-Hexafluoro-2,4-pentanedione (0.56 g, 2.70 mmol) is added to a solution of 2,6-dichloro-4-nitrophenylhydrazine (0.30 g, 2.35 mmol) in 20 ml of methanol chilled in an ice bath. The mixture is stirred overnight at RT, after which the methanol is removed in vacuo. The residue is dissolved in toluene and a catalytic amount of p-toluenesulfonic acid (pTSOH) added. The mixture is heated under reflux and stirred for 2 hours, after which it is allowed to cool to RT and the solvent is removed in vacuo. The resulting crystals are dissolved in xylene, 40 mg of pTSOH is added and the mixture is heated under reflux for 2 hours. The resulting mixture is cooled, washed with methylene chloride, concentrated in vacuo and purified by flash chromatography to give 3,5-bis(trifluoromethyl)-1-(2,6-dichloro-4-nitrophenyl)pyrazole. Following the procedure of Example 5, the nitrophenylpyrazole is reduced by treatment with platinum dioxide and hydrogen to give 3,5-dichloro-4-[3,5-bis-(trifluoromethyl)-1-pyrazolyl]aniline.

후처리

  1. temperaturechilled in an ice bath
  2. customafter which the methanol is removed in vacuo
  3. dissolutionThe residue is dissolved in toluene
  4. additiona catalytic amount of p-toluenesulfonic acid (pTSOH) added
  5. temperatureThe mixture is heated
  6. temperatureunder reflux
  7. stirringstirred for 2 hours
  8. temperatureto cool to RT
  9. customthe solvent is removed in vacuo
  10. dissolutionThe resulting crystals are dissolved in xylene
  11. addition40 mg of pTSOH is added
  12. temperaturethe mixture is heated
  13. temperatureunder reflux for 2 hours
  14. temperatureThe resulting mixture is cooled
  15. washwashed with methylene chloride
  16. concentrationconcentrated in vacuo
  17. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-b8938db0d95e41869078690fb869ed87
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04950678

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