Water → HCID 66697318, compound

HRID 2386789Notes

Reaction equation

HRID 2386789 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH2:12][C:13]([C:15]1[CH:26]=[CH:25][C:18]2[N:19]([CH3:24])[C:20](=[O:23])[N:21]([CH3:22])[C:17]=2[CH:16]=1)=[O:14].[CH3:27]I.O>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH:12]([CH3:27])[C:13]([C:15]1[CH:26]=[CH:25][C:18]2[N:19]([CH3:24])[C:20](=[O:23])[N:21]([CH3:22])[C:17]=2[CH:16]=1)=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66697385HCID 66697385, compound

Product 1

HCID 66697318HCID 66697318, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (55% in mineral oil, 139 mg) was added to a solution of 5-[2-(2-chloro-4-methoxy-phenyl)-acetyl]-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (1 g) in DMF (16 ml) at 0° C. The mixture was stirred for 30 min, then methyl iodide (0.2 ml) was added at 0° C. Water was added to the mixture and extracted with DCM. The combined organic layers were dried over Na2SO4 and concentrated to an oil. The residue was purified by flash chromatography (SiO2, 0 to 60% EtOAc/DCM) to give the title compound (830 mg) as light yellow oil. MS (m/e)=359.0 [M+H+].

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated to an oil
  4. customThe residue was purified by flash chromatography (SiO2, 0 to 60% EtOAc/DCM)

Sources & evidence

ORD record
ord-3821217ed43b4b96b181af3f22fd32a1
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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