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

HRID 730216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 730216
[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

Komponenten

5

Edukt 2

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

Produkt 1

HCID 11554756Benzo[b]thiophene-2-sulfonic acid [2-(4-chlorobenzenesulfonylamino)phenyl]-amideAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e6cfc0f2065d40288c9cdd74cf74a267
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07582673B2

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