Water → HCID 66697318, compound

HRID 2096800Notes

Reaction equation

HRID 2096800 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-f8c52940d6f242b49774f648910fc1de
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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