Phenylacetaldehyde → 3-Phenyl-2-({4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-amino)propanenitrile

HRID 2184075노트

반응식

HRID 2184075 반응식
[C:1]1([CH2:7][CH:8]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([C:14]#[N:15])(C)C.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1>C(Cl)Cl.O>[C:1]1([CH2:7][CH:8]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]([OH:32])([C:24]([F:25])([F:26])[F:27])[C:28]([F:29])([F:30])[F:31])=[CH:21][CH:22]=2)[C:14]#[N:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 3

HCID 998PhenylacetaldehydeHCID 82115Trimethylsilyl cyanideHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

생성물 1

HCID 224756413-Phenyl-2-({4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl}-amino)propanenitrile수율 63%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

To a mixture of phenylacetaldehyde (0.7 mL, 5.8 mmol) and trimethylsilyl cyanide 0.8 mL, 6.0 mmol) in CH2Cl2 (2 mL) was added 2-(4-aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (Oakwood, 1.6 g, 6.1 mmol). The resulting mixture was stirred at ambient temperature over 18 h. The reaction mixture was diluted with CH2Cl2 and water. The organics were washed several times with water, dried (MgSO4), and concentrated in vacuo. Purification by flash chromatography (8:1 hexanes/EtOAc) afforded the title compound as a pale yellow solid (1.4 g, 63%). MS (ES+) m/z 389 (MH+).

후처리

  1. washThe organics were washed several times with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by flash chromatography (8:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-98cb879f487c46668b7f0e75c9956936
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06900244B2

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