2-(Methylthio)benzimidazole → 1-{[2-(methylthio)-1H-benzimidazol-1-yl]methyl}-4-propylpyrrolidin-2-one

HRID 2358246Notes

Reaction equation

HRID 2358246 reaction equation
C(N(CC)C(=O)O[CH2:6][N:7]1[CH2:11][CH:10]([CH2:12][CH2:13][CH3:14])[CH2:9][C:8]1=[O:15])C.[CH3:19][S:20][C:21]1[NH:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1>C(#N)C>[CH3:19][S:20][C:21]1[N:22]([CH2:6][N:7]2[CH2:11][CH:10]([CH2:12][CH2:13][CH3:14])[CH2:9][C:8]2=[O:15])[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[N:25]=1

Participants

4

Reactant 2

HCID 235392-(Methylthio)benzimidazoleHCID 11448237(2-Oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate

Product 1

HCID 111508421-{[2-(methylthio)-1H-benzimidazol-1-yl]methyl}-4-propylpyrrolidin-2-oneYield 40.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (2-oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate a26 (1 eq, 3.18 mmol, 0.5 g) and 2-(methylthio)-benzimidazole (1.25 eq, 3.90 mmol, 0.64 g) in acetonitrile (4 ml) was heated under reflux for 42 h. The solvent was evaporated under reduce pressure and purification by preparative chromatography on reverse phase afforded 390 mg of 1-{[2-(methylthio)-1H-benzimidazol-1-yl]methyl}-4-propylpyrrolidin-2-one 90 (HPLC purity (U.V.): 85%; Yield: 40.3%).

Workup

  1. temperatureunder reflux for 42 h
  2. customThe solvent was evaporated
  3. custompressure and purification by preparative chromatography on reverse phase

Sources & evidence

ORD record
ord-dfb68b0cebcc4193b5a1c03c263d52dc
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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