Ethyl Acetate → 4-[2-(4-Iodo-phenoxy)-acetylamino]-thiophene-3-carboxylic acid methyl ester

HRID 14589

Reaktionsgleichung

[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:15])[CH2:12]CCl)=[CH:8][S:7][CH:6]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[I:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1.C(OCC)(=O)C>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH:10][C:11](=[O:15])[CH2:12][O:29][C:26]2[CH:27]=[CH:28][C:23]([I:22])=[CH:24][CH:25]=2)=[CH:8][S:7][CH:6]=1)=[O:4]

Komponenten

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

To a solution of 4-(3-chloro-propionylamino)-thiophene-3-carboxylic acid methyl ester ([51486-30-7], 2.0 g, 8.6 mmol) in dimethylformamide (30 mL) was added potassium carbonate (1.77 g, 12.8 mmol) and 4-iodophenol (2.26 g, 10.3 mmol) and the reaction mixture was then stirred overnight at 90° C. To the reaction mixture was added ethyl acetate (approximately 30 mL). The solid was filtered and washed with ethyl acetate. The filtrate was then reduced in vacuo and dissolved in dichloromethane (approximately 50 mL). The solution was filtered again over charcoal and to the filtrate was added isopropylether. After reducing the solution slowly in vacuo the solid was filtered to yield the title compound (3.57 g, 79%).

Aufarbeitung

filtrationThe solid was filtered
washwashed with ethyl acetate
dissolutiondissolved in dichloromethane (approximately 50 mL)
filtrationThe solution was filtered again over charcoal and to the filtrate
additionwas added isopropylether
filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag: ord-359696935bbe465abbd89b8f25825cb3
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07732452B2

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