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

HRID 2382679Notes

Reaction equation

HRID 2382679 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-d2c046555c054bc38f3d5439ebf7fb34
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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