Acetic Acid → (Z)-Ethyl 3-((2-amino-2-oxoethyl)amino)-3-(2,5-dimethoxyphenyl)acrylate

HRID 75536

Reaktionsgleichung

C[O-].[Na+].Cl.[NH2:5][CH2:6][C:7]([NH2:9])=[O:8].C(O)(=O)C.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[C:24](=O)[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]>CO>[NH2:9][C:7](=[O:8])[CH2:6][NH:5]/[C:24](/[C:17]1[CH:18]=[C:19]([O:22][CH3:23])[CH:20]=[CH:21][C:16]=1[O:15][CH3:14])=[CH:25]\[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

A 5-L reaction vessel was charged with methanol (3.3 L), sodium methoxide (102.4 g, 1.8 moles), and glycinamide hydrochloride (202 g, 1.8 moles). The mixture was heated at 65° C. for 1 hour before cooling to 50° C. and adding acetic acid (514.25 mmoles, 30.88 g, 29.47 mL) and ethyl 3-(2,5-dimethoxyphenyl)-3-oxopropanoate (300 g, 1.03 mole). After heating at reflux for 16 hours, the reaction mixture was stirred as it was cooled to 10° C. After 30 min the resulting solid was collected by vacuum filtration, pulling dry to form a cake that was dried in a vacuum oven (20 mm Hg, 65° C.) for 14 hours to afford the title compound (339.4 g).

Aufarbeitung

temperaturebefore cooling to 50° C.
temperatureAfter heating
temperatureat reflux for 16 hours
temperaturewas cooled to 10° C
filtrationAfter 30 min the resulting solid was collected by vacuum filtration
custompulling dry
customto form a cake that
customwas dried in a vacuum oven (20 mm Hg, 65° C.) for 14 hours

Quellen und Nachweise

ORD-Eintrag: ord-ae6cc591b0874408b7eafea63e8ea75b
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08835449B2

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