Acetic Anhydride → 3-Acetyl-1-benzenesulfonylindole-5-carboxylic acid methyl ester

HRID 1634295

Reaktionsgleichung

Reaktionsgleichung von HRID 1634295
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](OC(=O)C)(=[O:7])[CH3:6].[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH:20]=[CH:19]2)=[O:15]>ClC(Cl)C>[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[N:21]([S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)(=[O:26])=[O:27])[CH:20]=[C:19]2[C:5](=[O:7])[CH3:6])=[O:15]

Komponenten

5

Edukt 3

HCID 7918Acetic Anhydride2×HCID 6451240Aluminum(III) Chloride2×HCID 575174331H-Indole-5-carboxylic acid, 1-(phenylsulfonyl)-, methyl ester

Produkt 1

HCID 698902803-Acetyl-1-benzenesulfonylindole-5-carboxylic acid methyl esterAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel2×

Versuchsvorschrift

To a suspension of 10.7 g (80 mmol) of aluminum chloride in dichloroethane (80 ml) was added dropwise 4.83 g (40 mmol) of acetic anhydride. After stirring for 15 min, to the mixture was added dropwise 6.31 g (20 mmol) of the above-mentioned 1-benzenesulfonylindole-5-carboxylic acid methyl ester in dichloroethane (60 ml). After stirring for 2 hours at room temperature, to the mixture were added 5.33 g (40 mmol) of aluminum chloride and 2.04 g (20 mmol) of acetic anhydride. After stirring for 30 min, the mixture was poured into ice-water, extracted with ethyl acetate. The extract was washed twice with water, aqueous sodium bicarbonate and dried, and then concentrated. The obtained crystal was washed with isopropyl ether to give 6.82 g of 3-acetyl-1-benzenesulfonylindole-5-carboxylic acid methyl ester. Yield: 96%.

Aufarbeitung

  1. stirringAfter stirring for 2 hours at room temperature, to the mixture
  2. stirringAfter stirring for 30 min
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed twice with water, aqueous sodium bicarbonate
  5. customdried
  6. concentrationconcentrated
  7. washThe obtained crystal was washed with isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-90f8636fb2dd48a4ab4339c0f690cc78
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506787B2

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