Water → Ethyl 2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylate

HRID 649894

Reaktionsgleichung

Reaktionsgleichung von HRID 649894
[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].F[C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[F:23][C:21]1[CH:20]=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[C:17]([CH:22]=1)[NH:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 699464Ethyl 2-amino-1-benzothiophene-3-carboxylate

Produkt 1

HCID 18422317Ethyl 2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylateAusbeute 44,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Ethyl 2-aminobenzo[b]thiophene-3-carboxylate (69.3 g) and 2,4-difluoronitrobenzene (50 g) were dissolved in dimethyl sulfoxide (550 ml) and heated to 50° C. Thereto was added potassium carbonate (63 g) and the mixture was stirred at 100° C. for 70 min. After cooling, the reaction mixture was allowed to cool to 70° C. and poured into water (2.5 L). The reaction mixture was allowed to stand still, and filtered. The filtrated orange crystals were washed with ethyl acetate to give ethyl 2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylate (50.7 g).

Aufarbeitung

  1. temperatureAfter cooling
  2. temperatureto cool to 70° C.
  3. filtrationfiltered
  4. washThe filtrated orange crystals were washed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-81c6691c52ce497596d581f65bc3fe64
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06271225B1

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