Methanol → methyl 5-[N-acetyl-N-(2-methoxyethyl)amino]-4,7-dihydro-4,7-dioxobenzo[b]thiophene-2-carboxylate

HRID 1582186Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582186
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[C:7](=[O:20])[C:8]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[S:10][C:9]=2[C:17](=[O:19])[CH:18]=1.CO.[C:23](OC(=O)C)(=[O:25])[CH3:24]>S(=O)(=O)(O)O>[C:23]([N:5]([C:6]1[C:7](=[O:20])[C:8]2[CH:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[S:10][C:9]=2[C:17](=[O:19])[CH:18]=1)[CH2:4][CH2:3][O:2][CH3:1])(=[O:25])[CH3:24]

Komponenten

5

Edukt 3

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 12987499Methyl 4,7-dihydro-5-(2-methoxyethyl)amino-4,7-dioxobenzo[b]thiophene-2-carboxylate

Produkt 1

HCID 12987500methyl 5-[N-acetyl-N-(2-methoxyethyl)amino]-4,7-dihydro-4,7-dioxobenzo[b]thiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidKatalysator

Versuchsvorschrift

Five drops of concentrated sulfuric acid was added to a solution of methyl 4,7-dihydro-5-(2-methoxyethyl)amino-4,7-dioxobenzo[b]thiophene-2-carboxylate (1.2 g) in acetic anhydride (20 ml) and the mixture was stirred at room temperature for 1 hour. Methanol (20 ml) was gradually added to the reaction solution and then the solvent was evaporated. Water was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous sodium sulfate. After evaporation of the solvent, the residue was purified by silica gel column chromatography (elution with ethyl acetate-hexane 1:1 solution) to give methyl 5-[N-acetyl-N-(2-methoxyethyl)amino]-4,7-dihydro-4,7-dioxobenzo[b]thiophene-2-carboxylate (0.39 g) as a reddish brown powder.

Aufarbeitung

  1. customthe solvent was evaporated
  2. additionWater was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was purified by silica gel column chromatography (elution with ethyl acetate-hexane 1:1 solution)

Quellen und Nachweise

ORD-Eintrag
ord-2e2bbaa28f084a4fad4e4dc16740994c
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06734203B2

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