Water → 1-[2-(2-Fluoro-phenyl)-2-oxo-ethyl]-3-isopropenyl-1,3-dihydro-benzimidazol-2-one

HRID 1747353Notes

Reaction equation

[C:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]1=[O:13])([CH3:3])=[CH2:2].C(=O)([O-])[O-].[K+].[K+].[F:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23](=[O:26])[CH2:24]Br.O>CN(C=O)C.C(OCC)(=O)C>[F:20][C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][C:22]=1[C:23](=[O:26])[CH2:24][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:4]([C:1]([CH3:3])=[CH2:2])[C:5]1=[O:13]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 1-isopropenyl-1,3-dihydro-benzimidazol-2-one (1 g, 5.7 mmol) in DMF (50 ml) was added potassium carbonate (1.6 g, 11.5 mmol) followed by 2-fluorophenacyl bromide (1.5 g, 6.9 mmol). The resulting mixture was warmed to 80° C. for 2 h and cooled to ambient temperature. The reaction was poured into water and ethyl acetate and the layers were separated. The aqueous phase was extracted with ethyl acetate (2×) and the combined organics were dried (MgSO4). Filtration and concentration gave the crude product which was purified via column chromatography (silica gel, 50% EtOAc/hexanes). The product-containing fractions were combined and concentrated to give 1.6 g (90%) of the desired product.

Workup

temperaturecooled to ambient temperature
customthe layers were separated
extractionThe aqueous phase was extracted with ethyl acetate (2×)
dry with materialthe combined organics were dried (MgSO4)
filtrationFiltration and concentration
customgave the crude product which
customwas purified via column chromatography (silica gel, 50% EtOAc/hexanes)
concentrationconcentrated

Sources & evidence

ORD record: ord-b2aab438645747a9a7a61566b05551da
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

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