Water → Ethyl 5-nitro-1-benzothiophene-2-carboxylate

HRID 545478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545478
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.C([O-])([O-])=O.[K+].[K+].[CH2:19]([O:21][C:22](=[O:25])[CH2:23][SH:24])[CH3:20].O>CN(C=O)C>[CH2:19]([O:21][C:22]([C:23]1[S:24][C:2]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=2[CH:4]=1)=[O:25])[CH3:20]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 729332-Chloro-5-nitrobenzaldehyde

Produkt 1

HCID 737499Ethyl 5-nitro-1-benzothiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 2-chloro-5-nitro-benzaldehyde (31.01 g, 167.1 mmol) in 330 mL of anhydrous DMF at 0° C. was added K2CO3 (27.80 g, 201.1 mmol), followed by slow addition of mercapto-acetic acid ethyl ester (18.5 mL, 168.7 mmol). After stirring at 0° C. for 20 min, the resulting mixture was allowed to warm to rt and stir at rt overnight. The reaction mixture was then poured into 1.5 L of water. The solid formed was filtered and washed with 600 mL of water. After drying, 5-nitro-benzo[b]thiophene-2-carboxylic acid ethyl ester was obtained as pale solid. MS (EI): cal'd 252.0 (MH+), exp 252.1 (MH+).

Aufarbeitung

  1. temperatureto warm to rt
  2. stirringstir at rt overnight
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with 600 mL of water
  6. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-9f97d3dcf8c34e81b139d12cd1494b78
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935724B2

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