Methyl iodide → HCID 67107877, compound

HRID 1910802Notes

Reaction equation

HRID 1910802 reaction equation
[H-].[Na+].[CH:3]([C:6]1[NH:7][CH:8]=[C:9]([C:11]([CH3:22])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[CH3:12])[N:10]=1)([CH3:5])[CH3:4].I[CH3:24]>C1COCC1>[CH:3]([C:6]1[N:10]([CH3:24])[C:9]([C:11]([CH3:12])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[CH3:22])=[CH:8][N:7]=1)([CH3:5])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178440051HCID 178440051, compound

Product 1

HCID 67107877HCID 67107877, compoundYield 35.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) slurry of 50% sodium hydride (84 mg, 1.75 mmol) in THF (3 mL) was added 2-isopropyl-4-[1-methyl-1-(3-nitro-phenyl)-ethyl]-1H-imidazole (0.4 g, 1.46 mmol). The mixture was warmed to r.t. and stirred for 30 min. Iodomethane (0.13 mL, 2.1 mmol) was added and the reaction maintained for 2 h. The solvent was evaporated under reduced pressure and the residue partitioned between DCM and water. The organic phase was dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (60-120 mesh), eluting with 25% ethyl acetate/hexane to obtain 2-isopropyl-1-methyl-5-[1-methyl-1-(3-nitro-phenyl)-ethyl]-1H-imidazole (0.148 g, 35%) as a colourless semisolid.

Workup

  1. temperaturethe reaction maintained for 2 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue partitioned between DCM and water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (60-120 mesh)
  8. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-51ca71a431494b099a3ccdd7fe68e72c
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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