2,2,2-Trifluoroethanesulfonyl chloride → N-(4-(2,4-Difluorophenoxy)phenyl)-N-(2,2,2-trifluoroethanesulfonyl)amine

HRID 392464Notes

Reaction equation

HRID 392464 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][S:4](Cl)(=[O:6])=[O:5].[F:10][C:11]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:12]=1[O:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:10][C:11]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:12]=1[O:13][C:14]1[CH:15]=[CH:16][C:17]([NH:18][S:4]([CH2:3][C:2]([F:9])([F:8])[F:1])(=[O:6])=[O:5])=[CH:19][CH:20]=1

Participants

5

Reactant 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 226635574-(2,4-Difluorophenoxy)aniline

Product 1

HCID 22663792N-(4-(2,4-Difluorophenoxy)phenyl)-N-(2,2,2-trifluoroethanesulfonyl)amine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2,2,2-Trifluoroethanesulfonyl chloride (10.0 g, 54.8 mmol) was added dropwise to a solution of 4-(2,4-difluorophenoxy)aniline (11.0 g, 50.0 mmol) and 4-dimethylaminopyridine (9.1 g, 74.6 mmol) in methylene chloride (100 mL) at 0° C. under nitrogen. The mixture was slowly warmed to room temperature, stirring for a total of 72 h. The mixture was washed with saturated aqueous sodium bicarbonate solution (200 mL), dried over MgSO4, filtered and the solvent was removed under reduced pressure to afford the crude product as an orange oil. This residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/chloroform (1:4), to provide the title compound as a yellow solid: mp 105-108° C.; TLC Rf (1:9 ethyl acetate/chloroform)=0.75; 1H NMR (300 MHz, CDCl3) 7.23 (d, J=8.9 Hz, 2H), 7.14-6.87 (m, 3H), 6.93 (d, J=8.9 Hz, 2H), 3.76 (q, J=8.8 Hz, 2H) ppm; APCI MS m/z 366 [C14H10F5NO3S—H]−.

Workup

  1. washThe mixture was washed with saturated aqueous sodium bicarbonate solution (200 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customto afford the crude product as an orange oil
  6. customThis residue was purified by flash column chromatography on silica gel
  7. washeluting with ethyl acetate/chloroform (1:4)

Sources & evidence

ORD record
ord-9ccda2022aef43d18ce7f7bbfb526b89
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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