2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl 2-acetamido-1-benzothiophene-3-carboxylate

HRID 1594228

Reaktionsgleichung

Reaktionsgleichung von HRID 1594228
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=2[S:8][C:7]=1[NH:15][C:16](=[O:18])[CH3:17])=[O:5])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1.C([O-])(O)=O.[Na+]>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[S:8][C:7]=1[NH:15][C:16](=[O:18])[CH3:17])=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 986822-Acetylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl ester

Produkt 1

HCID 3722285Ethyl 2-acetamido-1-benzothiophene-3-carboxylateAusbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A solution of 1a (3.0 g, 11.24 mmol) in benzene (100 mL) was mixed with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (3.8 g, 16.85 mmol). The resultant mixture was heated at reflux for 2 h, diluted with saturated NaHCO3 solution (300 mL) and extracted with ethyl acetate (300 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated. Flash chromatography (hexanes/ethyl acetate, 8:1) then provided the title compound (1.06 g, 35%) as a yellow solid: MS (ES) m/z 264 (M+H)+;

Aufarbeitung

  1. temperatureat reflux for 2 h
  2. extractionextracted with ethyl acetate (300 mL, 3×)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ca82a885f0e3499ca73fc9c89411321a
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07300952B2

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