Water → 1,3-Diallyl-5-[2-(2-chloro-4-methoxy-phenyl)-propionyl]-1,3-dihydro-benzoimidazol-2-one

HRID 2096815Notes

Reaction equation

[Mg].[Cl:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11](Cl)[CH3:12].CON(C)[C:17]([C:19]1[CH:34]=[CH:33][C:22]2[N:23]([CH2:30][CH:31]=[CH2:32])[C:24](=[O:29])[N:25]([CH2:26][CH:27]=[CH2:28])[C:21]=2[CH:20]=1)=[O:18].O>C1COCC1>[CH2:30]([N:23]1[C:22]2[CH:33]=[CH:34][C:19]([C:17](=[O:18])[CH:11]([C:4]3[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=3[Cl:2])[CH3:12])=[CH:20][C:21]=2[N:25]([CH2:26][CH:27]=[CH2:28])[C:24]1=[O:29])[CH:31]=[CH2:32]

Participants

Conditions

Temperature: -10 °C

Procedure

A 1M suspension of Rieke magnesium in THF (1.3 ml) was added to THF (2 ml). The mixture was cooled to −10° C., and a solution of 2-chloro-1-(1-chloro-ethyl)-4-methoxy-benzene (136 mg) in THF (2 ml) was added. The mixture was stirred for 15 min. A solution of 1,3-diallyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methoxy-methyl-amide (100 mg) in THF (2 ml) was added at −10° C. The mixture was stirred overnight at room temperature. Water was added and extracted with EtOAc. The combined organic layers were dried over Na2SO4 and then concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane) to give the title compound (72 mg) as a light yellow foam. MS (m/e)=411.2 [M+H+].

Workup

stirringThe mixture was stirred overnight at room temperature
extractionextracted with EtOAc
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated to an oil
customThe residue was purified by flash chromatography (SiO2, 0 to 100% EtOAc/heptane)

Sources & evidence

ORD record: ord-7facfa80d763499b91d7a6a3c9ce14f8
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450313B2

Reaction notes

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