Sodium hydride → 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile

HRID 1040452Notes

Reaction equation

HRID 1040452 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[C:6]([C:8]#[N:9])[N:5]=[CH:4]1.[CH3:10][Si:11]([CH2:14][CH2:15][O:16][CH2:17]Cl)([CH3:13])[CH3:12]>C1COCC1>[CH3:10][Si:11]([CH3:13])([CH3:12])[CH2:14][CH2:15][O:16][CH2:17][N:3]1[CH:7]=[C:6]([C:8]#[N:9])[N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178510437HCID 178510437, compound

Product 1

HCID 584311371-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrileYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a round bottom flask was added NaH (60% in mineral oil) (200 mg, 5.22 mmol) in dry THF (12 ml), followed by the addition of 1H-imidazole-4-carbonitrile (400 mg, 4.3 mmol), SEMCl (1433 mg, 8.6 mmol). The reaction mixture was stirred at room temperature for 18 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc/sat. NaHCO3. The organic phase was separated, washed with water, brine, dried over anhy. Na2SO4, filtered and concentrated. The resulting residue was purified by flash chromatography on silica gel (0-3% MeOH/CH2Cl2). The product fractions were collected and concentrated to afford 355 mg of 1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-4-carbonitrile, m/z 224.6 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc/
  3. customThe organic phase was separated
  4. washwashed with water, brine
  5. customdried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography on silica gel (0-3% MeOH/CH2Cl2)
  9. customThe product fractions were collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5ddbc26188464738a1e1065c3d4f8871
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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