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

HRID 1021544Notes

Reaction equation

HRID 1021544 reaction equation
[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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 11068737tetrakis(acetonitrile)copper(I) hexafluorophosphateCatalystHCID 6342AcetonitrileSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-567edd0700a9435085e2bc6aec32b401
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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