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

HRID 600930Notes

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-c5fa6ec5c46f4df5904bc4a65ca6d4a4
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902241B2

Reaction notes

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