1,1'-Carbonyldiimidazole → Methyl 3-[3-(3-isopropylphenyl)-2-oxo-imidazolidin-1-yl]benzoate

HRID 751013Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH2:11][CH2:12][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH:20]([CH3:22])[CH3:21])[CH:15]=2)[CH:5]=1.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25]>ClCCCl>[CH:20]([C:16]1[CH:15]=[C:14]([N:13]2[CH2:12][CH2:11][N:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([O:2][CH3:1])=[O:23])[C:24]2=[O:25])[CH:19]=[CH:18][CH:17]=1)([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

To the solution of 3-[2-(3-isopropylphenylamino)ethylamino]benzoic acid methyl ester (0.83 g, 2.7 mmol) prepared above in dry 1,2-dichloroethane (5.0 mL) was added, under nitrogen, 1,1′-carbonyldiimidazole (0.65 g, 4.0 mmol). The mixture was then heated at 90° C. for 24 h. After cooling to room temperature, the mixture was washed with water, diluted HCl, water and brine, then dried over anhydrous Na2SO4 and concentrated. The crude product was obtained after the removal of the solvent and further purified by column chromatography (silica gel, hexanes:ethyl acetate, 9:1) to give methyl 3-[3-(3-isopropylphenyl)-2-oxo-imidazolidin-1-yl]benzoate as colorless needles (0.78 g, 85.7%). MS (ES+) m/z: 339.

Workup

additionwas added, under nitrogen
temperatureAfter cooling to room temperature
washthe mixture was washed with water, diluted HCl, water and brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customThe crude product was obtained
customafter the removal of the solvent
customfurther purified by column chromatography (silica gel, hexanes:ethyl acetate, 9:1)

Sources & evidence

ORD record: ord-9e91cc6b1f8c4acd815b0e6f152aaa42
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405233B2

Reaction notes

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