2-Amino-5-methylbenzenesulfonamide → 2-[2-(4-Chloro-2-methoxy-phenyl)-ethenesulfonylamino]-5-methyl-benzenesulfonamide

HRID 2283362Notes

Reaction equation

HRID 2283362 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][S:10](Cl)(=[O:12])=[O:11])=[C:4]([O:14][CH3:15])[CH:3]=1.[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[S:24]([NH2:27])(=[O:26])=[O:25]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][S:10]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[S:24]([NH2:27])(=[O:25])=[O:26])(=[O:12])=[O:11])=[C:4]([O:14][CH3:15])[CH:3]=1

Participants

4

Reactant 2

HCID 2455842-Amino-5-methylbenzenesulfonamideHCID 739930052-(4-Chloro-2-methoxyphenyl)-ethenesulfonyl chloride

Product 1

HCID 687826342-[2-(4-Chloro-2-methoxy-phenyl)-ethenesulfonylamino]-5-methyl-benzenesulfonamideYield 54%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(4-Chloro-2-methoxy-phenyl)-ethenesulfonyl chloride (0.50 g, 1.87 mmol) was added slowly to a solution of 2-amino-5-methyl-benzenesulfonamide (0.38 g, 2.05 mmol) in anhydrous pyridine (10 mL) and the reaction mixture was stirred for 18 hours at room temperature. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (30 mL). The organic phase was washed with 1 M hydrochloric acid and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography gave 0.42 g (54% yield) of the title compound.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (30 mL)
  3. washThe organic phase was washed with 1 M hydrochloric acid and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography

Sources & evidence

ORD record
ord-55df97f10b5d466da5ed2aaefe123d3a
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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