2-Aminobenzenesulfonamide → 2-[2-(4-Chloro-2-methoxy-phenyl)-ethenesulfonylamino]-benzenesulfonamide

HRID 2283274Notes

Reaction equation

HRID 2283274 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][S:21](Cl)(=[O:23])=[O:22])=[C:15]([O:25][CH3:26])[CH:14]=1>N1C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][S:21]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[S:8]([NH2:11])(=[O:9])=[O:10])(=[O:22])=[O:23])=[C:15]([O:25][CH3:26])[CH:14]=1

Participants

4

Reactant 2

HCID 728942-AminobenzenesulfonamideHCID 739930052-(4-Chloro-2-methoxyphenyl)-ethenesulfonyl chloride

Product 1

HCID 687831872-[2-(4-Chloro-2-methoxy-phenyl)-ethenesulfonylamino]-benzenesulfonamideYield 41%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Aminobenzene sulfonamide (194 mg, 1.13 mmol) was added in one portion to a solution of 2-(4-chloro-2-methoxyphenyl)-ethenesulfonyl chloride (300 mg, 1.13 mmol) in pyridine (3 mL) at RT. After 1 h stirring, no more starting material was detected by tlc. The reaction mixture was concentrated and the residue was taken up in ethyl acetate with a small amount of methanol. The organic phase was washed with 1N HCl, saturated sodium bicarbonate, dried over MgSO4 and concentrated under reduced pressure. The crude product was purified on silica gel using DCM/methanol, 99:1 to afford material which was further purified by recrystallization from methanol to give the title compound (184 mg, 41%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washThe organic phase was washed with 1N HCl, saturated sodium bicarbonate
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified on silica gel
  6. customto afford material which
  7. customwas further purified by recrystallization from methanol

Sources & evidence

ORD record
ord-d286d92c92884b89b6e3dc6bcfcd8ac6
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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