Dichloromethane → 5-bromo-4-chloro-2-fluoro-N-(2-methoxy-phenyl)-N-methyl-benzenesulfonamide

HRID 1891358Notes

Reaction equation

HRID 1891358 reaction equation
C(Cl)Cl.[Br:4][C:5]1[C:6]([Cl:16])=[CH:7][C:8]([F:15])=[C:9]([S:11](Cl)(=[O:13])=[O:12])[CH:10]=1.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][CH3:26].C(N(CC)CC)C>O>[Br:4][C:5]1[C:6]([Cl:16])=[CH:7][C:8]([F:15])=[C:9]([S:11]([N:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[O:18][CH3:17])[CH3:26])(=[O:13])=[O:12])[CH:10]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 27595792-Methoxy-N-methylanilineHCID 566047345-Bromo-4-chloro-2-fluoro-benzenesulfonyl chloride

Product 1

HCID 684711855-bromo-4-chloro-2-fluoro-N-(2-methoxy-phenyl)-N-methyl-benzenesulfonamideYield 61.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of DCM (36 mL) containing 5-bromo-4-chloro-2-fluoro-benzenesulfonyl chloride (5.5 g, 17.9 mmol) was added (2-methoxy-phenyl)-methyl-amine (2.6 g, 18.8 mmol) and triethylamine (7.1 mL, 53.7 mmol). The mixture was stirred for 16 hrs. 100 mL of DCM and 100 mL of water were added. The organic layer was separated, washed with water (2×50 mL) and dried over MgSO4. Concentration and purification by silica gel column chromatography eluting with hexane/ethyl acetate (9/1 to 5/1) yielded 5-bromo-4-chloro-2-fluoro-N-(2-methoxy-phenyl)-N-methyl-benzenesulfonamide as a white solid (4.5 g). MS: 408.0 (M+H)+; tR=8.83 min (method 2). NMR (CDCl3), δ, 7.925 (1H, d, J=6.9 Hz), 7.257-7.367 (3H, m), 6.959 (1H, m), 6.831 (1H, d, m), 3.490 (3H, s), 3.339 (3H, d, J=2.4 Hz).

Workup

  1. customThe organic layer was separated
  2. washwashed with water (2×50 mL)
  3. dry with materialdried over MgSO4
  4. concentrationConcentration and purification by silica gel column chromatography
  5. washeluting with hexane/ethyl acetate (9/1 to 5/1)

Sources & evidence

ORD record
ord-68a8ebfb0e2e4e339337ba81df5f5a8a
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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