Acetic Acid → 4-[(acetyloxy)methyl]-1,3-dihydro-5-(4-methoxybenzoyl)-2H-imidazol-2-one

HRID 370553

Reaktionsgleichung

Br[CH2:2][C:3]1[NH:7][C:6](=[O:8])[NH:5][C:4]=1[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1.[C:19]([OH:22])(=[O:21])[CH3:20]>C([O-])(=O)C.[Ag+].[Ag]Br>[C:19]([O:22][CH2:2][C:3]1[NH:7][C:6](=[O:8])[NH:5][C:4]=1[C:9](=[O:18])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)(=[O:21])[CH3:20]

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

5-(Bromomethyl)-1,3-dihydro-4-(4-methoxybenzoyl)-2H-imidazol-2-one (3.1 g) is dissolved in 80 ml of acetic acid by warming on a steam bath. The solution obtained is allowed to cool to about 25°-45° C. and 1.7 g of silver acetate is added. The mixture is stirred at 25° C. for 16 hours and the precipitate which forms (silver bromide) is removed by filtration. The filtrate is concentrated to about 10 ml and a solid crystallizes. This is separated by filtration and recrystallized from acetic acid to give 4-[(acetyloxy)methyl]-1,3-dihydro-5-(4-methoxybenzoyl)-2H-imidazol-2-one melting at about 155°-162° C. This compound has the following structural formula: ##STR7##

Aufarbeitung

temperatureby warming on a steam bath
customThe solution obtained
temperatureto cool to about 25°-45° C.
customis removed by filtration
concentrationThe filtrate is concentrated to about 10 ml
customa solid crystallizes
customThis is separated by filtration
customrecrystallized from acetic acid

Quellen und Nachweise

ORD-Eintrag: ord-b352a1b7a6e44e7789fb391720e00d48
Quelldatensatz: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04526981

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