4-Nitrobenzenesulfonamide → (RS)-S-Methyl-S-(4-nitrophenyl)-N-[(4-nitrophenyl)sulphonyl]sulphimide

HRID 548960Notes

Reaction equation

HRID 548960 reaction equation
C(O)(=O)C.C(O)(=O)C.I(C1C=CC=CC=1)=O.[CH3:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=1.[N+:28]([C:31]1[CH:36]=[CH:35][C:34]([S:37]([NH2:40])(=[O:39])=[O:38])=[CH:33][CH:32]=1)([O-:30])=[O:29].[O-2].[Mg+2]>ClCCl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[CH3:17][S:18]([C:19]1[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1)=[N:40][S:37]([C:34]1[CH:33]=[CH:32][C:31]([N+:28]([O-:30])=[O:29])=[CH:36][CH:35]=1)(=[O:39])=[O:38]

Participants

7

Reactant 4

HCID 227844-NitrobenzenesulfonamideHCID 961094-Nitrophenyl methyl sulfideHCID 6850729Magnesium monoxideHCID 73357407Acetic acid;iodosylbenzene

Product 1

HCID 59683175(RS)-S-Methyl-S-(4-nitrophenyl)-N-[(4-nitrophenyl)sulphonyl]sulphimideYield 74%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

879 mg (2.73 mmol) of iodosobenzene diacetate are added to a suspension of 300 mg (1.77 mmol) of 1-methylsulphanyl-4-nitrobenzene, 716 mg (3.55 mmol) of 4-nitrobenzenesulphonamide, 285 mg (7.10 mmol) of magnesium oxide and 78 mg (0.18 mmol) of rhodium(II) acetate dimer in 12 ml of dichloromethane at room temperature. The mixture is stirred for 24 h and then concentrated. The resulting residue is purified by chromatography (dichloromethane/ethanol 95:5). 484 mg (1.31 mmol; yield: 74%) of the product are obtained.

Workup

  1. concentrationconcentrated
  2. customThe resulting residue is purified by chromatography (dichloromethane/ethanol 95:5)
  3. custom484 mg (1.31 mmol; yield: 74%) of the product are obtained

Sources & evidence

ORD record
ord-618b738e40164c4286c0d8b868942ba5
Source dataset
uspto-grants-2011_05
Patent number
US07943629B2

Reaction notes

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