Dimethylformamide → Benzo[b]thiophene-2-propionic acid

HRID 1725601

Reaktionsgleichung

Reaktionsgleichung von HRID 1725601
[SH:1][CH2:2][C:3](OCC)=O.[CH3:8]N(C)C=O.[N+]([C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O)([O-])=O.[C:24](=[O:27])([O-])[O-:25].[K+].[K+]>O>[C:24]([CH2:8][CH2:3][C:2]1[S:1][C:16]2[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=2[CH:18]=1)([OH:25])=[O:27]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 111012-NitrobenzaldehydeHCID 11430Potassium CarbonateHCID 12185Ethyl Thioglycolate

Produkt 1

HCID 12713652Benzo[b]thiophene-2-propionic acidAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Ethyl 2-mercaptoacetate is added to a solution of dimethylformamide (800 ml), 2-nitrobenzaldehyde (73 g, 0.48 mol) and potassium carbonate (80 g, 0.57 mol) cooled to 0° C., while the temperature is maintained at 0° C. After stirring for 24 hours, the mixture is poured into 2 l of water and this aqueous phase is extracted with ether. The ether phase is dried over sodium sulfate and concentrated. The crude product obtained is purified on a column of alumina (petroleum ether) to give 34 g (35%) of a yellow oil.

Aufarbeitung

  1. temperatureis maintained at 0° C
  2. extractionthis aqueous phase is extracted with ether
  3. dry with materialThe ether phase is dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product obtained
  6. customis purified on a column of alumina (petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-6ca8b5f3e4834ee6953cf70138192c3c
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07491733B2

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