Potassium Carbonate → Ethyl 3-amino-6-nitro-1-benzothiophene-2-carboxylate

HRID 43797

Reaktionsgleichung

Reaktionsgleichung von HRID 43797
[N+]([C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7])([O-])=O.C(=O)([O-])[O-].[K+].[K+].[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH2:22][SH:23]>CN(C=O)C>[NH2:7][C:6]1[C:5]2[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:4]=2[S:23][C:22]=1[C:21]([O:25][CH2:26][CH3:27])=[O:24]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 5540822,4-Dinitrobenzonitrile

Produkt 1

HCID 67549245Ethyl 3-amino-6-nitro-1-benzothiophene-2-carboxylateAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2,4-Dinitrobenzonitrile (5.08 g, 26.3 mmol) was dissolved in DMF (55 ml). Potassium carbonate (4.36 g, 31.6 mmol) and ethyl thioglycolate (3.17 g, 26.3 mmol) were added, and the mixture was stirred at room temperature for three days. The reaction solution was concentrated under reduced pressure, diluted with ethyl acetate, washed with water, and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was recrystallized from ethyl acetate/hexane to obtain 2.27 g of the title compound as crystals (32%).

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentration under reduced pressure
  6. customthe residue was recrystallized from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-9fd42774e03b4419938ca01fdb1efa66
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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