m-Bromobenzenesulphonyl chloride → HCID 68782055, compound

HRID 2283303Notes

Reaction equation

HRID 2283303 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][C:3]=1[S:15]([NH2:18])(=[O:17])=[O:16].[Br:19][C:20]1[CH:21]=[C:22]([S:26](Cl)(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1>N1C=CC=CC=1>[Br:19][C:20]1[CH:21]=[C:22]([S:26]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([O:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[CH:4][C:3]=2[S:15]([NH2:18])(=[O:16])=[O:17])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 17943m-Bromobenzenesulphonyl chlorideHCID 68781949HCID 68781949, compound

Product 1

HCID 68782055HCID 68782055, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-5-phenoxybenzenesulfonamide (528 mg, 2 mmol) in pyridine (15 mL), 3-bromobenzenesulphonyl chloride (669.3 mg, 2.3 mmol) was added portionwise at 0° C. The reaction was stirred at RT overnight. The pyridine was removed in vacuo and the residue was dissolved in ethyl acetate. The organic phase was washed with aqueous 1N HCl, water and brine, dried over sodium sulfate, and concentrated under reduced pressure. The crude product was purified by flash column chromatography using ethyl acetate/hexane (1:3) as eluent to give the title compound (700 mg, 72%).

Workup

  1. customThe pyridine was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe organic phase was washed with aqueous 1N HCl, water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-189ef9061ec24529b20271b55cbf7db7
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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