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

HRID 2096815
Notes
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Reaction equation

HRID 2096815 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 5462224MagnesiumHCID 610834622-Chloro-1-(1-chloro-ethyl)-4-methoxy-benzeneHCID 866458781,3-Diallyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methoxy-methyl-amide

Product 1

HCID 666973501,3-Diallyl-5-[2-(2-chloro-4-methoxy-phenyl)-propionyl]-1,3-dihydro-benzoimidazol-2-oneYield 52.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

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

  1. stirringThe mixture was stirred overnight at room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated to an oil
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes