Water → 4-(3-Trifluoromethylphenoxy)-2-(4-Trifluoromethylphenyl)-Pyrimidine

HRID 411828

Reaktionsgleichung

Reaktionsgleichung von HRID 411828
O.Cl[C:3](Cl)(Cl)[CH2:4][CH:5](Cl)OCC.Cl.[F:13][C:14]([F:25])([F:24])[C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[NH:20])=[CH:17][CH:16]=1.[F:26][C:27]([F:36])([F:35])[C:28]1[CH:29]=[C:30]([OH:34])[CH:31]=[CH:32][CH:33]=1.C(=O)([O-])[O-].[K+].[K+].ClC(Cl)=CC=O>C(COC)OC>[F:26][C:27]([F:35])([F:36])[C:28]1[CH:29]=[C:30]([CH:31]=[CH:32][CH:33]=1)[O:34][C:3]1[CH:4]=[CH:5][N:21]=[C:19]([C:18]2[CH:22]=[CH:23][C:15]([C:14]([F:24])([F:25])[F:13])=[CH:16][CH:17]=2)[N:20]=1

Komponenten

8

Edukt 6

HCID 962WaterHCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 175543,3-Dichloro-2-propenalHCID 123508221,1,1,3-Tetrachloro-3-ethoxypropaneHCID 125357914-(Trifluoromethyl)benzamidine Hydrochloride2×

Produkt 1

HCID 99299504-(3-Trifluoromethylphenoxy)-2-(4-Trifluoromethylphenyl)-PyrimidineAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

Water (20 mmoles) is added to a solution of 1,1,1,3-tetrachloro-3-ethoxypropane (10 mmoles) in dimethoxyethane (25 ml). The reaction mixture is stirred for 2 h under reflux. The resulting mixture is slowly added to a mixture consisting of a 4-trifluoromethylbenzamidine hydrochloride (10 mmoles), 3-trifluoromethylphenol (11 mmoles), potassium carbonate (60 mmoles) and dimethoxyethane (50 ml), which is stirred under reflux. When the addition of 3,3-dichloroacrolein solution is completed additional 4-trifluoromethylbenzamidine hydrochloride (1 mmoles) is added. The reaction mixture is stirred for 2 hours under reflux and subsequently cooled down to ambient temperature, filtered through silica, and the organic phase is concentrated in vacuo. The residue is purified by chromatography on SiO2 (petrol ethers/diisopropylether: 6/1) to yield 3,07 g (80%) of the product having a melting point of 66-67° C.

Aufarbeitung

  1. temperatureunder reflux
  2. additionThe resulting mixture is slowly added to a mixture
  3. stirringis stirred
  4. temperatureunder reflux
  5. additionis added
  6. stirringThe reaction mixture is stirred for 2 hours
  7. temperatureunder reflux
  8. filtrationfiltered through silica
  9. concentrationthe organic phase is concentrated in vacuo
  10. customThe residue is purified by chromatography on SiO2 (petrol ethers/diisopropylether: 6/1)

Quellen und Nachweise

ORD-Eintrag
ord-c34d230f252a4708b6320892160c65d1
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06559307B2

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