Ethylenediaminetetraacetic Acid → Penflufen

HRID 1645386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1645386
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[N:12]([CH3:13])[N:11]=[C:10]([CH3:14])[C:9]=1[C:15]([NH2:17])=[O:16].CNC1CCCCC1NC.Br[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH:35]([CH3:40])[CH2:36][CH:37]([CH3:39])[CH3:38].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>[Cu](I)I.C1(C)C=CC=CC=1>[CH3:40][CH:35]([C:30]1[CH:29]=[CH:34][CH:33]=[CH:32][C:31]=1[NH:17][C:15]([C:9]1[C:10]([CH3:14])=[N:11][N:12]([CH3:13])[C:8]=1[F:7])=[O:16])[CH2:36][CH:37]([CH3:38])[CH3:39]

Komponenten

8

Edukt 5

HCID 6049Ethylenediaminetetraacetic AcidHCID 11430Potassium CarbonateHCID 5510741-N,2-N-dimethylcyclohexane-1,2-diamineHCID 112981065-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideHCID 252085081-Bromo-2-(1,3-dimethylbutyl)benzene

Produkt 1

HCID 11674113Penflufen

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 0.221 g (1.16 mmol) of copper iodide, 3.21 g (23.22 mmol) of potash and 2.189 g of 5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide is admixed under argon with 330 mg (2.322 mmol) of N,N′-dimethyl-1,2-cyclohexanediamine, 2.8 g (11.6 mmol) of 1-bromo-2-(1,3-dimethylbutyl)benzene and 30 ml of toluene. After boiling under reflux for one day, the mixture is poured onto water and 10 ml of a 5% EDTA solution. Subsequently, the mixture is extracted three times with ethyl acetate and concentrated by evaporation under reduced pressure. The oily residue is dissolved in toluene and stirred into n-hexane. After the precipitated crystals have been filtered off with suction, 3.3 g (89% of the theoretical yield) of N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide are obtained with a purity (HPLC) of 99%.

Aufarbeitung

  1. temperatureunder reflux for one day
  2. extractionSubsequently, the mixture is extracted three times with ethyl acetate
  3. concentrationconcentrated by evaporation under reduced pressure
  4. dissolutionThe oily residue is dissolved in toluene
  5. filtrationAfter the precipitated crystals have been filtered off with suction, 3.3 g (89% of the

Quellen und Nachweise

ORD-Eintrag
ord-1528f37c1eeb4a31b964c448b13daa7a
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124786B2

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