Methanesulfonamide → (RS)-S-(4-Nitrophenyl)-S-methyl-N-mesylsulphimide

HRID 548961Notes

Reaction equation

HRID 548961 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.[CH3:28][S:29]([NH2:32])(=[O:31])=[O:30].[O-2].[Mg+2]>ClCCl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[N+:25]([C:22]1[CH:21]=[CH:20][C:19]([S:18]([CH3:17])=[N:32][S:29]([CH3:28])(=[O:31])=[O:30])=[CH:24][CH:23]=1)([O-:27])=[O:26]

Participants

7

Reactant 4

HCID 72879MethanesulfonamideHCID 961094-Nitrophenyl methyl sulfideHCID 6850729Magnesium monoxideHCID 73357407Acetic acid;iodosylbenzene

Product 1

HCID 59683177(RS)-S-(4-Nitrophenyl)-S-methyl-N-mesylsulphimideYield 29%

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, 337 mg (3.55 mmol) of methanesulphonamide, 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). 133 mg (0.51 mmol; yield: 29%) of the product are obtained.

Workup

  1. concentrationconcentrated
  2. customThe resulting residue is purified by chromatography (dichloromethane/ethanol 95:5)
  3. custom133 mg (0.51 mmol; yield: 29%) of the product are obtained

Sources & evidence

ORD record
ord-06c18a7cc4ed40c8a13cf0baa5f8c74a
Source dataset
uspto-grants-2011_05
Patent number
US07943629B2

Reaction notes

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