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

HRID 411831

反応式

HRID 411831 の反応式
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

参加物

7

反応物 5

HCID 73763-(Trifluoromethyl)phenolHCID 107951,1-DimethoxyethaneHCID 11430Potassium CarbonateHCID 175543,3-Dichloro-2-propenal2 回HCID 2781916Cyclopropanecarboximidamide hydrochloride2 回

生成物 1

HCID 98604972-Cyclopropyl-4-(3-trifluoromethylphenoxy)pyrimidine収率 75%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

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).

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-1ec957835fbf4ea59e1c911d33f439c8
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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