2-Aminobenzenesulfonamide → 2-[[(E)-2-(4-Benzofuran-2-ylphenyl)ethenyl]sulfonylamino]benzenesulfonamide

HRID 2283259Notes

Reaction equation

HRID 2283259 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].[O:12]1[C:17]2=[CH:18][CH:19]=[CH:20][C:16]2=[CH:15][CH:14]=[C:13]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1/[CH:27]=[CH:28]/[S:29](Cl)(=[O:31])=[O:30]>N1C=CC=CC=1>[O:12]1[C:17]2=[CH:18][CH:19]=[CH:20][C:16]2=[CH:15][CH:14]=[C:13]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1/[CH:27]=[CH:28]/[S:29]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:9])=[O:10])(=[O:31])=[O:30]

Participants

4

Reactant 2

HCID 728942-AminobenzenesulfonamideHCID 86632000(E)-2-(4-benzofuran-2-ylphenyl)ethenesulfonyl chloride

Product 1

HCID 866319992-[[(E)-2-(4-Benzofuran-2-ylphenyl)ethenyl]sulfonylamino]benzenesulfonamideYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Aminobenzenesulfonamide (38 mg, 0.22 mmol) was dissolved in pyridine (2 ml), (E)-2-(4-benzofuran-2-ylphenyl)ethenesulfonyl chloride (70 mg, 0.22 mmol) was added and the mixture stirred for 2 h. The solvent was removed in vacuo and the residue was purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer) to give the title compound (46 mg, 46%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by preparative HPLC (XTerra MS C8 column, acetonitrile/ammonium acetate buffer)

Sources & evidence

ORD record
ord-f98fc5ad86e74249a4e08ca6fe18454e
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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