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m-Chloroperbenzoic acid → 2-nitro-N-(2-(oxiran-2-yl)ethyl)-N-phenylbenzenesulfonamide

HRID 404287
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HRID 404287 반응식
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]([N:16]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27])(=[O:19])=[O:18])[CH2:13][CH:14]=[CH2:15]>C(Cl)(Cl)Cl.O.C([O-])(O)=O.[Na+]>[N+:26]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[S:17]([N:16]([CH2:12][CH2:13][CH:14]1[CH2:15][O:9]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)(=[O:19])=[O:18])([O-:28])=[O:27]
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참가 물질

6

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 44131079N-(but-3-enyl)-2-nitro-N-phenylbenzenesulfonamide

생성물 1

HCID 580971922-nitro-N-(2-(oxiran-2-yl)ethyl)-N-phenylbenzenesulfonamide수율 97%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6212Chloroform용매
HCID 516892
Sodium Bicarbonate
용매

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온도
0 °C

실험 절차

mCPBA (77%, 0.0550 g, 0.246 mmol) was added to N-(but-3-enyl)-2-nitro-N-phenylbenzenesulfonamide (0.0653 g, 0.196 mmol) in 1 mL CHCl3 at 0° C. The mixture was stirred at 0° C. for 30 min, then gradually warmed up to room temperature and continued to stir for 18 hr. After TLC showed the disappearance of starting material, the reaction mixture was diluted with a 1:1 mixture of water and saturated NaHCO3 (2×10 mL) and water (10 mL). The organic layer was dried over anhydrous Na2SO4 and evaporated to afford the crude product, which was subjected to silica gel chromatography using Hexanes/EtOAc to afford 0.0662 g colorless oil as product, yield 96.9%.

후처리

  1. temperaturegradually warmed up to room temperature
  2. stirringto stir for 18 hr
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. customevaporated
  5. customto afford the crude product, which

출처 및 근거

ORD 기록
ord-ea8a6a5ef39141ab8782760242eef892
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08748473B2

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