Water → 4-benzyloxy-1-methyl-2-dimethylamino-1H-benzimidazole

HRID 636502Notes

Reaction equation

HRID 636502 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([NH:18][CH3:19])[N:14]([CH3:20])[C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]I.O>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([N:18]([CH3:23])[CH3:19])[N:14]([CH3:20])[C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 106594804-benzyloxy-1-methyl-2-methylamino-1H-benzimidazole

Product 1

HCID 106842294-benzyloxy-1-methyl-2-dimethylamino-1H-benzimidazoleYield 47.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-benzyloxy-1-methyl-2-methylamino-1H-benzimidazole (200 mg) in dimethylformamide (2 ml) was added sodium hydride (32.9 mg) under ice-cooling, and the mixture was stirred for 15 minutes. To the mixture was added methyl iodide (127 mg), and the mixture was stirred for 15 minutes under ice-cooling and then for 2 hours at ambient temperature. Water was added to the reaction mixture, and extracted with chloroform. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (chloroform:methanol=50:1, v/v) to give 4-benzyloxy-1-methyl-2-dimethylamino-1H-benzimidazole (100 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 15 minutes under ice-
  3. temperaturecooling
  4. waitfor 2 hours at ambient temperature
  5. extractionextracted with chloroform
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography (chloroform

Sources & evidence

ORD record
ord-cd427960f30f46b4a0720bcacabe6ebe
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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