4-Methoxy-2-nitrobenzenesulphonyl chloride → Benzo[b]thiophene-2-sulfonic acid [2-(4-methoxy-2-nitro-benzenesulfonylamino)phenyl]-amide

HRID 730218Notes

Reaction equation

HRID 730218 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][S:9]([C:12]1[S:16][C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[CH:13]=1)(=[O:11])=[O:10].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[C:25]([N+:33]([O-:35])=[O:34])[CH:24]=1>C(Cl)Cl.N1C=CC=CC=1>[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8][S:9]([C:12]2[S:16][C:15]3[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=3[CH:13]=2)(=[O:11])=[O:10])(=[O:30])=[O:31])=[C:25]([N+:33]([O-:35])=[O:34])[CH:24]=1

Participants

5

Reactant 2

HCID 874524-Methoxy-2-nitrobenzenesulphonyl chlorideHCID 86240018Benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)amide

Product 1

HCID 11613294Benzo[b]thiophene-2-sulfonic acid [2-(4-methoxy-2-nitro-benzenesulfonylamino)phenyl]-amideYield 67%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzo[b]thiophene-2-sulfonic acid (2-aminophenyl) amide (1 mmol, prepared as in Example 1) in DCM (2 mL) and pyridine (2 mL), 4-methoxy-2-nitrobenzenesulfonyl chloride (1.1 mmol) was added at RT and the reaction mixture was then allowed to stir at RT overnight. The reaction mixture was then diluted with DCM (10 mL). The organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL) and brine (10 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM/EtOAc to obtain 348 mg of benzo[b]thiophene-2-sulfonic acid [2-(4-methoxy-2-nitro-benzenesulfonylamino)phenyl]-amide. LC: Tr 1.09 min; MS: 520.7 (M+1)+.

Workup

  1. washThe organic phase was washed with 10% aqueous HCl (10 mL), water (10 mL) and brine (10 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by flash column chromatography
  6. washeluting with DCM/EtOAc

Sources & evidence

ORD record
ord-527c11158a444d93bf584513855c198a
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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