Potassium Carbonate → 2-Methyl-3-[2-(4-nitro-phenyl)-ethyl]-5,5-diphenyl-3,5-dihydro-imidazol-4-one

HRID 507401

Reaktionsgleichung

[CH3:1][C:2]1[NH:6][C:5](=[O:7])[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:3]=1.Br[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][C:2]1[N:6]([CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([N+:29]([O-:31])=[O:30])=[CH:27][CH:28]=2)[C:5](=[O:7])[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 70 °C

Versuchsvorschrift

2-Methyl-5,5-diphenyl-3,5-dihydro-imidazol-4-one (1 g, 4 mmol) and 1-(2-bromo-ethyl)-4-nitro-benzene (919 mg, 4 mmol) and potassium carbonate (669 mg, 4.8 mmol) are dissolved in 12 mL acetone and the reaction mixture is heated at 70° C. for 5 min in the microwave oven (Biotage Initiator) and again heated for 5 min at 120° C. The mixture is cooled to room temperature, filtered and the filtrate evaporated to yield the crude product which is subjected to flash chromatography. ISCO Companion CombiFlash, 80 g silica gel, cyclohexane/ethyl acetate, followed by a second purification step, 40 g silica gel, acetone/cylohexane to yield 2-methyl-3-[2-(4-nitro-phenyl)-ethyl]-5,5-diphenyl-3,5-dihydro-imidazol-4-one (750 mg, 45%). LC/MS at 254 nm; [M+H] 400; Rt 3.391 min.

Aufarbeitung

temperatureagain heated for 5 min at 120° C
temperatureThe mixture is cooled to room temperature
filtrationfiltered
customthe filtrate evaporated
customto yield the crude product which
customISCO Companion CombiFlash, 80 g silica gel, cyclohexane/ethyl acetate, followed by a second purification step, 40 g silica gel, acetone/cylohexane

Quellen und Nachweise

ORD-Eintrag: ord-71e545d6397c40efb131e2111786c2ee
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07786155B2

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