Reaction #738914

Reaction equation

3,3-dichloroacrolein

3-trifluoromethylphenol

potassium carbonate

cyclopropylcarbamidine hydrochloride

cyclopropylcarbamidine hydrochloride

3,3-Dichloroacrolein

→

pure product

Yield 75.0%

2-cyclopropyl-4-(3-trifluoromethylphenoxy)pyrimidine

Yield 75.0%

Solvents

dimethoxyethane

dimethoxyethane

Conditions

Workup

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

Procedure

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 mmoles) and dimethoxyethane (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 (CDCl3); δ=2.10 ppm (m, N═C(═N)—CH).

Source