Sodium Hydroxide → 2-Anilino-5-phenylthiophene-3-carboxylic acid

HRID 1967157Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1967157
[NH:1]([C:8]1[S:9][C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:11][C:12]=1[C:13]([O:15]CC)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.Cl.O.C(OCC)(=O)C>[NH:1]([C:8]1[S:9][C:10]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:11][C:12]=1[C:13]([OH:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 2

HCID 14798Sodium HydroxideHCID 58256479Ethyl 2-anilino-5-phenylthiophene-3-carboxylate

Produkt 1

HCID 582564742-Anilino-5-phenylthiophene-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of ethyl 2-anilino-5-phenylthiophene-3-carboxylate (51.7 mg, 0.160 mmol) in ethanol (3 mL) was added water (0.6 mL) and aqueous sodium hydroxide solution (2 M, 0.400 ml, 0.799 mmol). The reaction suspension was heated to 80° C. to afford a clear yellow solution; after one hour the suspension was allowed to cool to room temperature before being diluted with an aqueous hydrogen chloride solution (2 M, 1 mL), water (1.5 mL), and ethyl acetate (10 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (5 mL). The combined organic layers were combined and concentrated to afford 2-anilino-5-phenylthiophene-3-carboxylic acid.

Aufarbeitung

  1. customto afford a clear yellow solution
  2. temperatureto cool to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (5 mL)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8f6e7ec8a746425fabfb7f9b73d02a28
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420695B2

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