Water → 4-Benzyloxy-6-bromo-1-methoxymethyl-2-methyl-1H-benzimidazole

HRID 969528Notes

Reaction equation

HRID 969528 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[NH:14][C:13]=2[CH:12]=[C:11]([Br:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:23][O:24][CH3:25].O>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([CH2:23][O:24][CH3:25])[C:13]=2[CH:12]=[C:11]([Br:19])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 672202147-(benzyloxy)-5-bromo-2-methyl-1H-benzo[d]imidazole

Product 1

HCID 691352384-Benzyloxy-6-bromo-1-methoxymethyl-2-methyl-1H-benzimidazoleYield 26.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

2.0 g (6.3 mmol) 4-Benzyloxy-6-bromo-2-methyl-1H-benzimidazole were solved in dimethylformamide (10 ml) and the solution was cooled to 0° C. 151 mg (6.5 mmol) sodium hydride (60%) were added in portions and the reaction was stirred for 20 min. 435 μl (6.3 mmol) 1-Chloro-1-methoxy-methane were added and the reaction was stirred at 0° C. After 2 h the mixture was poured into water (200 ml) and extracted with ethyl acetate. The organic layers were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel (toluene/dioxane=6:1) to afford 0.6 g (26%) of the title compound as a yellow oil.

Workup

  1. stirringthe reaction was stirred at 0° C
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layers were dried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (toluene/dioxane=6:1)

Sources & evidence

ORD record
ord-0e4e6c3d99c64eb5bf8d5d65fa1fc9d2
Source dataset
uspto-grants-2007_12
Patent number
US07307084B2

Reaction notes

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