N-(2-aminophenyl)-4-chlorobenzenesulfonamide → Benzo[b]thiophene-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amide

HRID 730216Notes

Reaction equation

HRID 730216 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[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[S:19]1[C:23]([S:24](Cl)(=[O:26])=[O:25])=[CH:22][C:21]2[CH:28]=[CH:29][CH:30]=[CH:31][C:20]1=2>C(Cl)Cl.N1C=CC=CC=1>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([S:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][S:24]([C:23]2[S:19][C:20]3[CH:31]=[CH:30][CH:29]=[CH:28][C:21]=3[CH:22]=2)(=[O:25])=[O:26])(=[O:11])=[O:10])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 241359N-(2-aminophenyl)-4-chlorobenzenesulfonamideHCID 27763331-Benzothiophene-2-sulfonyl chloride

Product 1

HCID 11554756Benzo[b]thiophene-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amideYield 75.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(2-aminophenyl)-4-chlorobenzenesulfonamide (0.5 mmol, prepared as in Example 11) in DCM (1 mL) and pyridine (1 mL), benzo[b]thiophene-2-sulfonyl chloride (0.55 mmol), prepared as above, was added at RT and the reaction mixture was then allowed to stir at RT overnight or until the reaction was complete as determined by TLC or LC-MS. The reaction mixture was then diluted with DCM (5 mL). The organic phase was washed with 10% HCl aqueous solution (5 mL), water (5 mL) and brine (5 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 afford 180 mg of benzo[b]thiophene-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amide. LC: Tr 1.23 min, MS: 479.8 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-e6cfc0f2065d40288c9cdd74cf74a267
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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