Sodium hydride → 2-Chloro-1-[[2-(trimethylsilanyl)ethoxy]methyl]-benzimidazole

HRID 553453Notes

Reaction equation

HRID 553453 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[H-].[Na+].[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18]Cl>CN(C=O)C>[CH3:13][Si:14]([CH3:21])([CH3:20])[CH2:15][CH2:16][O:17][CH2:18][N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[Cl:1]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 785722-ChlorobenzimidazoleHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 597528982-Chloro-1-[[2-(trimethylsilanyl)ethoxy]methyl]-benzimidazoleYield 60.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-1H-benzo[d]imidazole (1 g, 6.6 mmol.) in dry DMF (10 mL) was added sodium hydride (60%, 0.26 g, 6.5 mmol.) at room temperature under nitrogen atmosphere. 2-(trimethylsilyl)ethoxymethyl chloride (SEMCl, 1.14 g, 6.8 mmol.) was added dropwise after the solution stirred for 1.5 h. The resulting mixture stirred overnight and then quenched with water and extracted with ethyl acetate (30 mL×3). The combined organic layers was washed with water, dried over sodium sulfate and concentrated to give a residue. The residue was purified by column chromatography to give 1-((2-(trimethylsilyl)ethoxy)methyl)-2-chloro-1H-benzo[d]imidazole (1.13 g, 60.8%).

Workup

  1. stirringThe resulting mixture stirred overnight
  2. customquenched with water
  3. extractionextracted with ethyl acetate (30 mL×3)
  4. washThe combined organic layers was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customto give a residue
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b811916265cc42fe96013d0183c43469
Source dataset
uspto-grants-2011_11
Patent number
US08048862B2

Reaction notes

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