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

HRID 411829

반응식

HRID 411829 반응식
Cl[C:2](Cl)=[CH:3][CH:4]=[O:5].Cl.[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[NH:14])=[CH:11][CH:10]=1.[F:18][C:19]([F:28])([F:27])[C:20]1[CH:21]=[C:22](O)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(COC)OC>[Cl:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]2[N:15]=[C:4]([O:5][C:24]3[CH:23]=[CH:22][CH:21]=[C:20]([C:19]([F:28])([F:27])[F:18])[CH:25]=3)[CH:3]=[CH:2][N:14]=2)=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 175543,3-Dichloro-2-propenal2회HCID 2034364-Chlorobenzene-1-carboximidamide hydrochloride2회

생성물 1

HCID 98632542-(4-Chlorophenyl)-4-(3-trifluoromethylphenoxy)pyrimidine수율 80%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매2회

실험 절차

3,3-Dichloroacrolein (10 mmoles) diluted with dimethoxyethane (35 ml), is slowly added to a mixture consisting of a 4-chlorobenzamidine 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 4-chlorobenzamidine 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 2.79 g (80%) of the pure product having a melting point of 92° C.

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-50784cb5d79444a4869a3c09146eedc7
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559307B2

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