2-Acetylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl ester → HCID 2830693, Verbindung

HRID 1351242

Reaktionsgleichung

Reaktionsgleichung von HRID 1351242
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH2:17][CH2:16][CH2:15][C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2].S([O-])([O-])(=O)=[O:20].[Ce+4].S([O-])([O-])(=O)=O>C(O)(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH2:18][CH2:17][CH2:16][C:15](=[O:20])[C:8]=2[S:9][C:10]=1[NH:11][C:12](=[O:14])[CH3:13])=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 986822-Acetylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl esterHCID 159684Ceric sulfate

Produkt 1

HCID 2830693HCID 2830693, VerbindungAusbeute 29,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of 2-Acetylamino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid ethyl ester (140 g) in acetic acid (1.5 L) and water (1.5 L) was added gradually cerium (IV) sulfate 4 hydrate (900 g) with vigorously stirring. After the solution was stirred overnight, the solid was removed by filtration and the filtrate was concentrated. The solution was then neutralized with aqueous ammonia and extracted 3 times with ethyl acetate-tetrahydrofuran (=4:1). The organic layers were combined and evaporated in vacuo. The resulting solid was washed with tetrahydrofuran to provide the title compound (44 g) as a pale yellow solid.

Aufarbeitung

  1. stirringAfter the solution was stirred overnight
  2. customthe solid was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. extractionextracted 3 times with ethyl acetate-tetrahydrofuran (=4:1)
  5. customevaporated in vacuo
  6. washThe resulting solid was washed with tetrahydrofuran

Quellen und Nachweise

ORD-Eintrag
ord-fb6ee0870ef94dcd9f3de61a065dd6d4
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217723B2

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