P-Anisidine → 3-Amino-N-(4-methoxyphenyl)-4-phenylthiophene-2-carboxamide

HRID 1775603

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C[Al](C)C.[NH2:14][C:15]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][S:17][C:16]=1[C:26](OC)=[O:27]>C1(C)C=CC=CC=1>[NH2:14][C:15]1[C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:18][S:17][C:16]=1[C:26]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:27]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

p-Anisidine (29 mg, 0.24 mmol) was dissolved in toluene (2 ml) in a reaction vessel, and trimethylaluminum (2 M in TIIF, 0.12 ml) was added thereto at 0° C. After stirring for 10 min, to the mixture was added methyl 3-amino-4-phenylthiophene-2-carboxylate (50 mg, 0.21 mmol). The resulting mixture was heated to reflux at 120° C. for 16 hr. The completion of the reaction was confirmed by TLC. The reaction mixture was allowed to cool to room temperature, extracted with EtOAc, dried over anhydrous MgSO4, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography (hexane:EtOAc=5:1) to give (57 mg, 0.18 mmol, 84% yield) of the title compound.

Aufarbeitung

customat 0° C
temperatureThe resulting mixture was heated
temperatureto cool to room temperature
extractionextracted with EtOAc
dry with materialdried over anhydrous MgSO4
concentrationconcentrated under reduced pressure
customThe concentrate was purified by silica gel column chromatography (hexane:EtOAc=5:1)

Quellen und Nachweise

ORD-Eintrag: ord-9d507646114648c5bd9f984a4ea6a178
Quelldatensatz: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09260448B2

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