Trifluoroacetamide → N-[(R)-Cyclopropyl(4-nitrophenyl)oxidosulphanylidene]-2,2,2-trifluoroacetamide

HRID 1027844Notes

Reaction equation

HRID 1027844 reaction equation
[CH:1]1([S:4]([C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)=[O:5])[CH2:3][CH2:2]1.[F:15][C:16]([F:21])([F:20])[C:17]([NH2:19])=[O:18].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[O-2].[Mg+2]>C(Cl)Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[CH:1]1([S:4]([C:6]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)(=[N:19][C:17](=[O:18])[C:16]([F:21])([F:20])[F:15])=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 67717TrifluoroacetamideHCID 6850729Magnesium monoxideHCID 12217721Iodo benzene diacetateHCID 595508341-(Cyclopropanesulfinyl)-4-nitrobenzene

Product 1

HCID 56949254N-[(R)-Cyclopropyl(4-nitrophenyl)oxidosulphanylidene]-2,2,2-trifluoroacetamideYield 78%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

1.58 g (3.58 mmol) of rhodium(II) acetate dimer was added, under argon, to a suspension of 15.1 g (71.53 mmol) (RS)-1-cyclopropane sulfinyl-4-nitrobenzene, 17.8 g (157.37 mmol) trifluoroacetamide, 38.0 g (118.02 mmol) iodobenzene diacetate and 12.7 g (314.73 mmol) magnesium oxide in 801 ml DCM and stirred overnight at room temperature. The mixture was filtered through Celite with suction and concentrated by evaporation. The residue that remained was purified chromatographically (hexane/ethyl acetate 2:1). 18.0 g (55.97 mmol; yield: 78%) of the product was obtained.

Workup

  1. filtrationThe mixture was filtered through Celite with suction
  2. concentrationconcentrated by evaporation
  3. customThe residue that remained was purified chromatographically (hexane/ethyl acetate 2:1)
  4. custom18.0 g (55.97 mmol; yield: 78%) of the product was obtained

Sources & evidence

ORD record
ord-434cfd0f4f854c89bf2637102c98f939
Source dataset
uspto-grants-2014_05
Patent number
US08735412B2

Reaction notes

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