Reaktion #499013

Reaktionsgleichung

dimethyoxyethane

3-trifluoromethylphenol

potassium carbonate

3,3-dichloroacrolein

cyclopropylcarbamidine hydrochloride

cyclopropylcarbamidine hydrochloride

3,3-Dichloroacrolein

→

pure product

Ausbeute 75.0%

2-Cyclopropyl-4-(3-Trifluoromethylphenoxy) Pyrimidine

Ausbeute 75.0%

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis slowly added to a mixture
2. 2
   Temperaturunder reflux
3. 3
   workup.ADDITIONis added
4. 4
   workup.STIRRINGThe reaction mixture is stirred for 3 hours
5. 5
   Temperaturunder reflux
6. 6
   Filtrationfiltered through silica
7. 7
   EinengenThe organic phase is concentrated in vacuo
8. 8
   SonstigeThe residue was purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 20/1)

Vorschrift

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).

Quelle