m-Bromobenzenesulphonyl chloride → 2-(3-Bromobenzenesulfonylamino)-5-methyl-benzensulfonamide

HRID 2283296Notes

Reaction equation

HRID 2283296 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[Br:13][C:14]1[CH:15]=[C:16]([S:20](Cl)(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1>N1C=CC=CC=1>[Br:13][C:14]1[CH:15]=[C:16]([S:20]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=2[S:9]([NH2:12])(=[O:10])=[O:11])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 17943m-Bromobenzenesulphonyl chlorideHCID 2455842-Amino-5-methylbenzenesulfonamide

Product 1

HCID 687814742-(3-Bromobenzenesulfonylamino)-5-methyl-benzensulfonamideYield 63%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-5-methyl-benzenesulfonamide (Example 45a) (6.0 g, 32.3 mmol) in pyridine (20 mL), 3-bromobenzenesulphonyl chloride (8.24 g, 32.3 mmol) was added portionwise at 0° C. The reaction was stirred at RT for 10 h. The pyridine was removed in vacuo at 35° C. 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 (1:1) as eluent to give the title compound (8 g, 63%).

Workup

  1. customThe pyridine was removed in vacuo at 35° C.
  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-a937258c5a454c3a9582c6413dd4c337
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

Loading…