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4-Chlorostyrene → 2-(4-Chlorophenyl)-1-(4-nitrophenylsulfonyl)aziridine

HRID 510780
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HRID 510780 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[CH:4][CH:3]=1.[N+:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:22]=C2CCCCI2C2C=CC=CC=2)(=[O:21])=[O:20])=[CH:15][CH:14]=1)([O-:12])=[O:11]>C(#N)C.CC#N.CC#N.CC#N.CC#N.F[P-](F)(F)(F)(F)F.[Cu+]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][N:22]2[S:19]([C:16]2[CH:15]=[CH:14][C:13]([N+:10]([O-:12])=[O:11])=[CH:18][CH:17]=2)(=[O:21])=[O:20])=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 140854-ChlorostyreneHCID 86651740(N-(p-nitrophenylsulfonyl)imino)phenyliodinane

생성물 1

HCID 118584672-(4-Chlorophenyl)-1-(4-nitrophenylsulfonyl)aziridine수율 81.8%

시약·촉매·용매 2

HCID 11068737tetrakis(acetonitrile)copper(I) hexafluorophosphate촉매HCID 6342Acetonitrile용매

실험 절차

To a suspension of 1-chloro-4-vinylbenzene (0.1195 ml, 0.9957 mmol), tetrakis(acetonitrile)copper(I) hexafluorophosphate (0.01856 g, 0.04979 mmol), and 4 angstrom molecular sieves (300 mg) in dry acetonitrile (2.5 ml) degassed with argon was added [N-[(p-nitrophenyl)sulfonyl]imino]phenyliodinane (0.6037 g, 1.494 mmol) portion-wise over 2 hours as a solid. It was stirred overnight under argon, then was loaded directly onto a Biotage SP1 system eluting with a 2-30% linear gradient of EtOAc in hexanes to yield 276 mg of the title compound (81.8% yield).

후처리

  1. customdegassed with argon
  2. washeluting with a 2-30% linear gradient of EtOAc in hexanes

출처 및 근거

ORD 기록
ord-0cf970067f88441290d75e45c2b70257
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096567B2

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