Sulfuric Acid → 5-Chloro-2-(ethoxycarbonyl)-1-(phenylsulfonyl)-1H-indole-3-sulfonic acid

HRID 260485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 260485
[S:1](=[O:5])(=O)([OH:3])[OH:2].[C:6]([C:11]1[N:12]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:23])=[O:22])[C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([Cl:20])=[CH:15][CH:14]=2)([O:8][CH2:9][CH3:10])=[O:7]>C(OC(=O)C)(=O)C.ClCCl>[C:6]([C:11]1[N:12]([S:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[O:22])=[O:23])[C:13]2[C:18]([C:19]=1[S:1]([OH:3])(=[O:5])=[O:2])=[CH:17][C:16]([Cl:20])=[CH:15][CH:14]=2)([O:8][CH2:9][CH3:10])=[O:7]

Komponenten

5

Edukt 2

HCID 1118Sulfuric AcidHCID 22401489ethyl 5-chloro-1-(phenylsulfonyl)-1H-indole-2-carboxylate

Produkt 1

HCID 224015045-Chloro-2-(ethoxycarbonyl)-1-(phenylsulfonyl)-1H-indole-3-sulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 7918Acetic AnhydrideLösungsmittel

Versuchsvorschrift

Concentrated sulfuric acid (2.50 ml, 90 mmol) was added dropwise over 5 min at 0° C. to a stirred solution of 2-carboethoxy-5-chloro-1-phenylsulfonylindole (7.28 g, 20.0 mmol) in acetic anhydride (10 ml) and dry dichloromethane (50 ml). The resulting tan solution was warmed to RT (room temperature) and after 3 hours was poured onto ice and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried (Na2SO4) and evaporated in vacuo to a syrup. Residual acetic anhydride was removed by azeotroping with toluene (3×50 ml), and the residue was crystallized from dichloromethane. The dichloromethane was evaporated in vacuo to give the title compound as a tan powder:

Aufarbeitung

  1. additionafter 3 hours was poured onto ice
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo to a syrup
  6. customResidual acetic anhydride was removed
  7. customby azeotroping with toluene (3×50 ml)
  8. customthe residue was crystallized from dichloromethane
  9. customThe dichloromethane was evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a4073bd5786745159d1df1d99396482d
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05527819

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