Potassium Carbonate → 4-(3-Trifluoromethylphenoxy)-2-(4-Trifluoromethylphenyl)-Pyrimidine

HRID 411826

Reaction equation

HRID 411826 reaction equation
FC(F)(F)C1C=C(C=CC=1)O[C:7]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)=[CH:8][CH:9]=O.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:37]=[CH:36][C:32]([C:33]([NH2:35])=[NH:34])=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:21][C:18]([F:19])([F:20])[C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:11][C:7]1[CH:8]=[CH:9][N:35]=[C:33]([C:32]2[CH:31]=[CH:30][C:29]([C:28]([F:27])([F:38])[F:39])=[CH:37][CH:36]=2)[N:34]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27773904-(Trifluoromethyl)benzenecarboximidamideHCID 18541697HCID 18541697, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3,3-bis-(3-trifluoromethylphenoxy)-acrolein (10 mmoles), 4-trifluoromethylbenzamidine (10 mmoles), potassium carbonate (10 mmoles) and acetonitril (100 ml), is stirred at 80° C. for four hours. The reaction mixture is cooled down to ambient temperature and filtered through silica. The organic phase is washed with ethyl acetate and concentrated in vacuo. The residue is purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 2/1) to yield 3.06 g (80%) of the pure product having a melting point of 66° C.

Workup

  1. temperatureThe reaction mixture is cooled down to ambient temperature
  2. filtrationfiltered through silica
  3. washThe organic phase is washed with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 2/1)

Sources & evidence

ORD record
ord-ab955588beac4678837f619742f8937b
Source dataset
uspto-grants-2003_05
Patent number
US06559307B2

Linked notes

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