Trifluoromethylsulfonamide → HCID 59683172, compound

HRID 548962Notes

Reaction equation

HRID 548962 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH3:13])=[CH:8][CH:7]=1)=[O:4].[F:16][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])([F:19])[F:18].[O-2].[Mg+2].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1>CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O.[Rh+2].[Rh+2].ClCCl>[CH3:13][S:12]([C:9]1[CH:10]=[CH:11][C:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:14])[F:15])=[CH:7][CH:8]=1)=[N:23][S:20]([C:17]([F:19])([F:18])[F:16])(=[O:22])=[O:21]

Participants

7

Reactant 4

HCID 79001TrifluoromethylsulfonamideHCID 266341HCID 266341, compoundHCID 6850729Magnesium monoxideHCID 12217721Iodo benzene diacetate

Product 1

HCID 59683172HCID 59683172, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 152122Dirhodium tetraacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

2.44 g (10.4 mmol) of 2,2,2-trifluoro-N-(4-methylsulphanylphenyl)acetamide and 2.80 g (18.8 mmol) of trifluoromethylsulphonamide are mixed with 145 ml of dichloromethane. 2.09 g (51.9 mmol) of magnesium oxide, 460 mg (1.04 mmol) of rhodium(II) acetate dimer and 6.68 g (20.75 mmol) of iodobenzene diacetate are added to the mixture. The mixture is stirred at room temperature for 1 hour and then filtered, and the filter cake is washed with dichloromethane. On concentration of the filtrate, crystals separate out and are filtered off with suction and washed with a little dichloromethane. Drying results in 3.60 g (9.42 mmol; yield: 91%) of the product.

Workup

  1. filtrationfiltered
  2. washthe filter cake is washed with dichloromethane
  3. customOn concentration of the filtrate, crystals separate out
  4. filtrationare filtered off with suction
  5. washwashed with a little dichloromethane
  6. customDrying
  7. customresults in 3.60 g (9.42 mmol; yield: 91%) of the product

Sources & evidence

ORD record
ord-6e0e543e8ee54d28b79424045cda3610
Source dataset
uspto-grants-2011_05
Patent number
US07943629B2

Reaction notes

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