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

HRID 651729

Reaction equation

HRID 651729 reaction equation
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

Participants

8

Reactant 6

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-3a1cc3098a754159b141577cb43d17d3
Source dataset
uspto-grants-2001_08
Patent number
US06281358B1

Linked notes

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