3-(Trifluoromethyl)phenol → 2-Cyclopropyl-4-(3-trifluoromethylphenoxy)pyrimidine

HRID 411831

Reaktionsgleichung

Reaktionsgleichung von HRID 411831
Cl[C:2](Cl)=[CH:3][CH:4]=[O:5].[CH2:7]1[CH:9]([C:10]([NH2:12])=[NH:11])[CH2:8]1.Cl.[F:14][C:15]([F:24])([F:23])[C:16]1[CH:17]=[C:18](O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].COC(OC)C>C(COC)OC>[CH:9]1([C:10]2[N:12]=[C:4]([O:5][C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([C:15]([F:24])([F:23])[F:14])[CH:21]=3)[CH:3]=[CH:2][N:11]=2)[CH2:8][CH2:7]1

Komponenten

7

Edukt 5

HCID 73763-(Trifluoromethyl)phenolHCID 107951,1-DimethoxyethaneHCID 11430Potassium CarbonateHCID 175543,3-Dichloro-2-propenal2×HCID 2781916Cyclopropanecarboximidamide hydrochloride2×

Produkt 1

HCID 98604972-Cyclopropyl-4-(3-trifluoromethylphenoxy)pyrimidineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

3,3-Dichloroacrolein (10 mmoles) diluted with dimethoxyethane (35 ml), is slowly added to a mixture consisting of a cyclopropylcarbamidine hydrochloride (10 mmoles), 3-trifluoromethylphenol (11 mmoles), potassium carbonate (40 rnmoles) and dimethyoxyethane (40 ml), which is stirred under reflux. When the addition of 3,3-dichloroacrolein is completed additional cyclopropylcarbamidine hydrochloride (1 mmoles) is added. The reaction mixture is stirred for 3 hours under reflux and subsequently cooled down to ambient temperature over night and filtered through silica. The organic phase is concentrated in vacuo. The residue was purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 20/1) to yield 2.1 g (75%) of the pure product having as a colorless liquid; 1H NMR (CDC13); δ=2.10 ppm (m, N═C(═N)═CH).

Aufarbeitung

  1. additionis slowly added to a mixture
  2. temperatureunder reflux
  3. additionis added
  4. stirringThe reaction mixture is stirred for 3 hours
  5. temperatureunder reflux
  6. filtrationfiltered through silica
  7. concentrationThe organic phase is concentrated in vacuo
  8. customThe residue was purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 20/1)

Quellen und Nachweise

ORD-Eintrag
ord-1ec957835fbf4ea59e1c911d33f439c8
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559307B2

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