Methyl iodide → 1-Cyclobutyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester

HRID 1828187Notes

Reaction equation

HRID 1828187 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:18]=[CH:17][C:8]2[N:9]([CH:13]3[CH2:16][CH2:15][CH2:14]3)[C:10](=[O:12])[NH:11][C:7]=2[CH:6]=1)=[O:4].[H-].[Na+].I[CH3:22]>CS(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[CH:18]=[CH:17][C:8]2[N:9]([CH:13]3[CH2:16][CH2:15][CH2:14]3)[C:10](=[O:12])[N:11]([CH3:22])[C:7]=2[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 695855151-cyclobutyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester

Product 1

HCID 695853001-Cyclobutyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl esterYield 98.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 1-cyclobutyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester (17.01 g, 69.1 mmol) in methyl sulfoxide (60 ml) was added sodium hydride (2.76 g as a 60% dispersion in oil, 69 mmol). The reaction mixture was stirred for 30 minutes prior to the dropwise addition of iodomethane (4.3 ml, 69.1 mmol). The reaction was stirred for 1 hour, was diluted with water and extracted with ethyl acetate. The organic layer was dried with sodium sulfate and concentrated in vacuo to give 17.76 g of 1-Cyclobutyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid methyl ester.

Workup

  1. stirringThe reaction was stirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8eaeffe3d1974e689d93cce52d626fde
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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