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3-(Trifluoromethyl)aniline → 5-Oxo-3-(3-(trifluoromethyl)phenylamino)cyclohex-3-enecarboxylic acid

HRID 517191
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HRID 517191 반응식
O=[C:2]1[CH2:7][C:6](=[O:8])[CH2:5][CH:4]([C:9]([OH:11])=[O:10])[CH2:3]1.[F:12][C:13]([F:22])([F:21])[C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O.[OH-].[Na+]>O.CN(C)C=O>[O:8]=[C:6]1[CH2:5][CH:4]([C:9]([OH:11])=[O:10])[CH2:3][C:2]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:14]([C:13]([F:12])([F:21])[F:22])[CH:15]=2)=[CH:7]1
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참가 물질

7

반응물 4

HCID 73753-(Trifluoromethyl)anilineHCID 14798Sodium HydroxideHCID 2733225Ytterbium triflateHCID 143714583,5-Dioxocyclohexane-1-carboxylic acid

생성물 1

HCID 867323105-Oxo-3-(3-(trifluoromethyl)phenylamino)cyclohex-3-enecarboxylic acid

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3,5-dioxocyclohexanecarboxylic acid (1.00 g, 6.41 mmol), 3-(trifluoromethyl)aniline (880 μL, 1.14 g, 4.05 mmol), Ytterbium(III) trifluormethanesulfonate (20 mg, 32 μmol, 0.5 mol %) and N,N-dimethylformamide (3 mL) is stirred at room temperature over night. Water and aqueous sodium hydroxide are added and the mixture is washed with diethyl ether. The organic layer is discarded, and the aqueous layer is acidified with aqueous hydrogen chloride and extracted with diethyl ether. The organic layer is dried over Na2SO4 and concentrated under reduced pressure. Yield: 1.30 g; ESI mass spectrum [M+H]+=300, Retention time HPLC: 1.08 min (V001—006).

후처리

  1. washthe mixture is washed with diethyl ether
  2. extractionextracted with diethyl ether
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. custom1.08 min (V001—006)

출처 및 근거

ORD 기록
ord-e11995f4bf174f3eb075eea376459803
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09115093B2

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