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3-Fluoro-4-(trifluoromethyl)benzaldehyde → (NE,S)-N-[[3-fluoro-4-(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide

HRID 2370762
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HRID 2370762 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH:5]=O.[CH3:14][C:15]([S@@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])/[CH:5]=[N:20]/[S@:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19]
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참가 물질

5

반응물 2

HCID 27375373-Fluoro-4-(trifluoromethyl)benzaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

생성물 1

HCID 89310589(NE,S)-N-[[3-fluoro-4-(trifluoromethyl)phenyl]methylidene]-2-methylpropane-2-sulfinamide

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 3-fluoro-4-(trifluoromethyl)benzaldehyde (5.7 g, 29.7 mmol) in DCM (60 mL) was added (S)-2-methylpropane-2-sulfinamide (7.19 g, 59.3 mmol) and copper (II) sulfate (18.94 g, 119 mmol). The suspension was stirred at rt under N2 for 20 h. The suspension was then filtered through Celite® brand filter agent, and the solids were washed with DCM (2×20 mL). The filtrates were concentrated and purified by ISCO (120 g, SiO2, 10-50% EtOAc/hexanes) to give (S,E)-N-(3-fluoro-4-(trifluoromethyl)benzylidene)-2-methylpropane-2-sulfinamide as a white solid.

후처리

  1. filtrationThe suspension was then filtered through Celite® brand
  2. filtrationfilter agent
  3. washthe solids were washed with DCM (2×20 mL)
  4. concentrationThe filtrates were concentrated
  5. custompurified by ISCO (120 g, SiO2, 10-50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-f75cb5a45aee4b2dbd0bd1efb5c7a54c
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08710043B2

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