Trifluoroacetamide → HCID 89451651, compound

HRID 2277739Notes

Reaction equation

HRID 2277739 reaction equation
[CH3:1][S:2]([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=[O:3].[F:14][C:15]([F:20])([F:19])[C:16]([NH2:18])=[O:17].[O-2].[Mg+2].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2]>[F:14][C:15]([F:20])([F:19])[C:16]([N:18]=[S:2]([CH3:1])([CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=[O:3])=[O:17]

Participants

7

Reactant 4

HCID 67717TrifluoroacetamideHCID 6850729Magnesium monoxideHCID 12217721Iodo benzene diacetateHCID 89262547HCID 89262547, compound

Product 1

HCID 89451651HCID 89451651, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of (rac)-1-[(methylsulfinyl)methyl]-3-nitrobenzene (16.6 g; 83.1 mmol), trifluoroacetamide (18.8 g; 166.1 mmol), magnesium oxide (13.4 g; 332.3 mmol) and rhodium(II)-acetate dimer (1.7 g; 8.3 mmol) in DCM (2290 mL) was added iodobenzene diacetate (40.1 g; 124.6 mmol) at room temperature. The batch was stirred for 16 hours at room temperature, filtered and concentrated. The residue was purified by chromatography (DCM/ethanol 97:3) to give the desired product (25.6 g; 82.4 mmol).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was purified by chromatography (DCM/ethanol 97:3)

Sources & evidence

ORD record
ord-e277a905d0eb4c54825ad706cd6076e0
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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