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

HRID 1027844
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 tetraacetateCatalyst
HCID 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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08735412B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes