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Sodium Chloride → N-[1-Cyclopropyl-2,2-difluoro-2-(phenylsulfonyl)ethyl]-2-methyl-2-propanesulfinamide

HRID 1970972
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HRID 1970972 반응식
[CH:1]1(/[CH:4]=[N:5]/[S:6]([C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])[CH2:3][CH2:2]1.[F:12][CH:13]([F:23])[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Na+].[Cl-]>C1COCC1>[CH:1]1([CH:4]([NH:5][S:6]([C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7])[C:13]([F:12])([F:23])[S:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:15])=[O:16])[CH2:2][CH2:3]1
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참가 물질

6

반응물 4

HCID 5234Sodium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 11816356((Difluoromethyl)sulfonyl)benzeneHCID 12171914(E)-N-(cyclopropylmethylene)-2-methylpropane-2-sulfinamide

생성물 1

HCID 59543160N-[1-Cyclopropyl-2,2-difluoro-2-(phenylsulfonyl)ethyl]-2-methyl-2-propanesulfinamide

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

To a solution of N-[(1E)-cyclopropylmethylene]-2-methylpropane-2-sulfinamide (1.0 g, 5.8 mmol) and [(difluoromethyl)sulfonyl]benzene (1.1 g, 5.8 mmol) in THF (60 mL) was added dropwise NaHMDS (2 M, 4 mL, 8.2 mmol) at −78° C. The reaction mixture was stirred at this temperature for 2 h. A saturated NaCl solution (60 mL) was added to the reaction mixture to quench the reaction at −78° C. After warmed to room temperature, the mixture was extracted with EtOAc. The combined organic phases were dried, concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (400 MHz, CDCl3) δ 7.80 (d, 2H); 7.60 (t, 1H); 7.48 (d, 2H); 3.48 (d, 1H); 1.06-1.10 (m, 1H); 1.05 (s, 9H); 0.45-0.75 (m, 4H).

후처리

  1. customto quench
  2. customthe reaction at −78° C
  3. extractionthe mixture was extracted with EtOAc
  4. customThe combined organic phases were dried
  5. concentrationconcentrated
  6. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-94202cccd19b4ba8872463f484d9f6f8
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08431569B2

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