Triethylamine → HCID 35177757, Verbindung

HRID 1049960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1049960
CS[C:3]([S:13][CH3:14])=[C:4]([C:10](=O)[CH3:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(O)(=O)C.[C:19]([NH2:27])(=[NH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>C(O)C>[CH3:11][C:10]1[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:3]([S:13][CH3:14])[N:27]=[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:26]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 4997384Butanoic acid, 2-[bis(methylthio)methylene]-3-oxo-, ethyl esterHCID 12238987Benzenecarboximidamide, monoacetate

Produkt 1

HCID 35177757HCID 35177757, VerbindungAusbeute 60,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-(bis(methylthio)methylene)-3-oxobutanoate (500 mg, 2 mmol) in ethanol was added benzamidine acetate (732 mg, 6 mmol) and triethyl amine (1.41 mL) and the reaction mixture was refluxed overnight. The reaction mixture was concentrated and partitioned between ethyl acetate and water and the organic layer washed with water and dried over Na2SO4 and the solvent evaporated in vacuum. The crude product was purified by column chromatography over silica gel using 1% ethyl acetate in petroleum ether as eluent to give the desired product (350 mg). 1H-NMR 400 Hz (CDCl3): δ 8.50 (d, J=7.6 Hz, 2H), 7.50-7.46 (m, 3H), 4.45 (q, J=7.2 Hz, 2H), 2.67 (s, 3H), 2.65 (s, 3H), 1.44 (t, J=7.2 Hz, 3H); MS m/z 288.7 (M+1).

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompartitioned between ethyl acetate and water
  4. washthe organic layer washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent evaporated in vacuum
  7. customThe crude product was purified by column chromatography over silica gel using 1% ethyl acetate in petroleum ether as eluent

Quellen und Nachweise

ORD-Eintrag
ord-7cc380c8dd94472d8ddbc567fbf4f0ef
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382277B2

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