5-Bromo-6-chloropyridine-3-sulfonyl chloride → 5-bromo-6-chloro-N-[2-(2,4-dichlorophenoxy)phenyl]pyridine-3-sulfonamide

HRID 746751Notes

Reaction equation

HRID 746751 reaction equation
Cl.[Cl:2][C:3]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:4]=1[O:5][C:6]1[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=1[NH2:8].[Br:18][C:19]1[CH:20]=[C:21]([S:26](Cl)(=[O:28])=[O:27])[CH:22]=[N:23][C:24]=1[Cl:25]>N1C=CC=CC=1.C(OCC)(=O)C.Cl>[Br:18][C:19]1[CH:20]=[C:21]([S:26]([NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C:4]2[CH:13]=[CH:14][C:15]([Cl:17])=[CH:16][C:3]=2[Cl:2])(=[O:28])=[O:27])[CH:22]=[N:23][C:24]=1[Cl:25]

Participants

6

Reactant 2

HCID 27936265-Bromo-6-chloropyridine-3-sulfonyl chlorideHCID 2795482Benzenamine, 4-(2,4-dichlorophenoxy)-, hydrochloride

Product 1

HCID 38564715-bromo-6-chloro-N-[2-(2,4-dichlorophenoxy)phenyl]pyridine-3-sulfonamide

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(2,4-Dichlorophenoxy)aniline HCl (1.14 g, 3.94 mmol) and 5-bromo-6-chloropyridine-3-sulfonyl chloride (1.26 g, 4.33 mmol) were dissolved in pyridine (4 mL) and allowed to stir at ambient temperature for 1 hour. The reaction mixture was then diluted with 100 mL of ethyl acetate, 80 mL of 0.5 M HCl. The organic layer was washed successively with 100 mL of 0.5 M HCl, twice with 100 mL of water, 100 mL of half-saturated brine and finally 100 mL of brine. Drying of the organic layer over sodium sulfate was followed by filtration and solvent removal under reduced pressure. The resulting residue was purified by silica gel chromatography (linear gradient 60-100% DCM in hexanes) to yield 5-bromo-6-chloro-N-[2-(2,4-dichlorophenoxy)phenyl]pyridine-3-sulfonamide, giving proton NMR and mass spectral data consistent with theory.

Workup

  1. washThe organic layer was washed successively with 100 mL of 0.5 M HCl, twice with 100 mL of water, 100 mL of half-saturated brine and finally 100 mL of brine
  2. dry with materialDrying of the organic layer over sodium sulfate
  3. filtrationwas followed by filtration and solvent removal under reduced pressure
  4. customThe resulting residue was purified by silica gel chromatography (linear gradient 60-100% DCM in hexanes)

Sources & evidence

ORD record
ord-6cdd4dbc66f34f7e8dffe72e4108591c
Source dataset
uspto-grants-2008_07
Patent number
US07393873B2

Reaction notes

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