2-Amino-5-methylbenzenesulfonamide → 2-(2,3-Dichloro-benzenesulfonylamino)-5-methyl-benzenesulfonamide

HRID 2283301Notes

Reaction equation

HRID 2283301 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].[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[S:21](Cl)(=[O:23])=[O:22]>N1C=CC=CC=1>[Cl:13][C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][C:15]=1[S:21]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:10])=[O:11])(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 2455842-Amino-5-methylbenzenesulfonamideHCID 27342222,3-Dichlorobenzene-1-sulfonyl chloride

Product 1

HCID 577509312-(2,3-Dichloro-benzenesulfonylamino)-5-methyl-benzenesulfonamideYield 607.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-amino-5-methyl-benzenesulfonamide (1.86 g, 1 mmol) in pyridine (20 mL), 2,3-dichlorobenzenesulphonyl chloride (3.0 g, 1.25 mmol) was added at 0° C. The reaction was stirred at RT for 17 h. 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 (1:1) as eluent to give the title compound (2.4 g, 60%).

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-83f38265213d4d089a65c1d60b72b7b1
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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