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

HRID 411829

反応式

HRID 411829 の反応式
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

参加物

6

反応物 4

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 175543,3-Dichloro-2-propenal2 回HCID 2034364-Chlorobenzene-1-carboximidamide hydrochloride2 回

生成物 1

HCID 98632542-(4-Chlorophenyl)-4-(3-trifluoromethylphenoxy)pyrimidine収率 80%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-50784cb5d79444a4869a3c09146eedc7
出典データセット
uspto-grants-2003_05
特許番号
US06559307B2

関連ノート

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