3-(Trifluoromethyl)phenol → 2-Cyclopropyl-4-(3-trifluoromethylphenoxy)pyrimidine

HRID 411831

반응식

HRID 411831 반응식
Cl[C:2](Cl)=[CH:3][CH:4]=[O:5].[CH2:7]1[CH:9]([C:10]([NH2:12])=[NH:11])[CH2:8]1.Cl.[F:14][C:15]([F:24])([F:23])[C:16]1[CH:17]=[C:18](O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].COC(OC)C>C(COC)OC>[CH:9]1([C:10]2[N:12]=[C:4]([O:5][C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([C:15]([F:24])([F:23])[F:14])[CH:21]=3)[CH:3]=[CH:2][N:11]=2)[CH2:8][CH2:7]1

참가 물질

7

반응물 5

HCID 73763-(Trifluoromethyl)phenolHCID 107951,1-DimethoxyethaneHCID 11430Potassium CarbonateHCID 175543,3-Dichloro-2-propenal2회HCID 2781916Cyclopropanecarboximidamide hydrochloride2회

생성물 1

HCID 98604972-Cyclopropyl-4-(3-trifluoromethylphenoxy)pyrimidine수율 75%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

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).

후처리

  1. additionis slowly added to a mixture
  2. temperatureunder reflux
  3. additionis added
  4. stirringThe reaction mixture is stirred for 3 hours
  5. temperatureunder reflux
  6. filtrationfiltered through silica
  7. concentrationThe organic phase is concentrated in vacuo
  8. customThe residue was purified by chromatography on Al2O3 (petrol ethers/ethyl acetate: 20/1)

출처 및 근거

ORD 기록
ord-1ec957835fbf4ea59e1c911d33f439c8
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559307B2

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