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

HRID 2199510Notes

Reaction equation

HRID 2199510 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

A suspension of (RS)-1-cyclopropanesulphinyl-4-nitrobenzene, trifluoroacetamide, iodobenzene diacetate and magnesium oxide in DCM was admixed, under argon, with rhodium(II) acetate dimer and stirred overnight at room temperature. The mixture was filtered off with suction over Celite and concentrated by evaporation. The remaining residue was purified by means of chromatography (hexane/acetic ester 2:1) (yield: 78%).

Workup

  1. filtrationThe mixture was filtered off with suction over Celite
  2. concentrationconcentrated by evaporation
  3. customThe remaining residue was purified by means of chromatography (hexane/acetic ester 2:1) (yield: 78%)

Sources & evidence

ORD record
ord-5553505048354ffa84a33f9a9e44629f
Source dataset
uspto-grants-2016_06
Patent number
US09359306B2

Reaction notes

Loading…