Ethanesulfonyl chloride → N-(4-(2,4-Difluorophenoxy)phenyl)-N-ethylsulfonylamine

HRID 392463Notes

Reaction equation

HRID 392463 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[F:7][C:8]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:9]=1[O:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[F:7][C:8]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:9]=1[O:10][C:11]1[CH:12]=[CH:13][C:14]([NH:15][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 226635574-(2,4-Difluorophenoxy)aniline

Product 1

HCID 22663741N-(4-(2,4-Difluorophenoxy)phenyl)-N-ethylsulfonylamine

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Ethanesulfonyl chloride (9.4 mL, 99 mmol) was added dropwise over 5 min to a dark gray solution of 4-(2,4-difluorophenoxy)aniline (20.0 g, 90 mmol) and 4-dimethylaminopyridine (16.6 g, 136 mmol) in methylene chloride (180 mL) at room temperature under nitrogen, after which the mixture was stirred at room temperature for 26 h. The mixture was washed with saturated aqueous sodium bicarbonate solution (200 mL), brine (100 mL), dried over MgSO4, filtered and the solvent was removed under reduced pressure to afford the crude product as an amber oil. This residue was triturated with diethyl ether (300 mL) and filtered to provide an amber solid. This material was further purified by flash column chromatography on silica gel, eluting with ethyl acetate/chloroform (1:9), to provide the title compound as an off-white powder: 1H NMR (300 MHz, DMSO-d6) 9.69 (s, 1H), 7.52-7.44 (m, 1H), 7.28-7.09 (m, 2H), 7.20 (d, J=8.8 Hz, 2H), 6.95 (d, J=8.8 Hz, 2H), 3.03 (q, J=7.6 Hz, 2H), 2.50 (t, J=1.6 Hz, 3H).

Workup

  1. washThe mixture was washed with saturated aqueous sodium bicarbonate solution (200 mL), brine (100 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 amber oil
  6. customThis residue was triturated with diethyl ether (300 mL)
  7. filtrationfiltered
  8. customto provide an amber solid
  9. customThis material was further purified by flash column chromatography on silica gel
  10. washeluting with ethyl acetate/chloroform (1:9)

Sources & evidence

ORD record
ord-384455b494fe4875a46b1ed96d60b62c
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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