Methyl iodide → N-(1-methylimidazol-2-yl)benzylideneamine

HRID 741708Notes

Reaction equation

HRID 741708 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:14]C(C)([O-])C.[K+].CI>CN(C=O)C>[CH3:14][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[N:6]=[CH:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 53795682N-[(1E)-phenylmethylidene]-1H-imidazol-2-amine

Product 1

HCID 53843952N-(1-methylimidazol-2-yl)benzylideneamineYield 49.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(2-imidazolyl)benzylideneamine (0.2 g) was dissolved in DMF (4 ml), and potassium t-butoxide (0.15 g) and methyl iodide (0.18 g) were added. The mixture was stirred at room temperature for 3 hours. The solvent was evaporated, and water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (eluent: chloroform). The resulting crude crystals were recrystallized from diethyl ether--hexane to give the title compound (0.1 g, 49.9%) as pale yellow needles.

Workup

  1. customThe solvent was evaporated
  2. additionwater was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (eluent: chloroform)
  8. customThe resulting crude crystals were recrystallized from diethyl ether

Sources & evidence

ORD record
ord-4e1abe74d4f54f24aa0ee8eaf6f59d0b
Source dataset
uspto-grants-1996_09
Patent number
US05552427

Reaction notes

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