Dinitrofluorobenzene → 1-(2,4-Dinitrophenyl)-2-(chloromethyl)imidazole

HRID 1587485Notes

Reaction equation

HRID 1587485 reaction equation
Cl.[Cl:2][CH2:3][C:4]1[NH:5][CH:6]=[CH:7][N:8]=1.[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1F)([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:9]([C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[N:5]1[CH:6]=[CH:7][N:8]=[C:4]1[CH2:3][Cl:2])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 6264DinitrofluorobenzeneHCID 11430Potassium CarbonateHCID 27609292-(Chloromethyl)-1H-imidazole hydrochloride

Product 1

HCID 156371921-(2,4-Dinitrophenyl)-2-(chloromethyl)imidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(Chloromethyl)imidazole hydrochloride (920 mg) was dissolved in 5 ml of acetonitrile. To this solution was added 830 μL of 2,4-dinitrofluorobenzene and 2.5 g of potassium carbonate. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and water. The organic layer was dried (sodium sulfate) and concentrated. The crude reaction product was purified by flash silica gel chromatography (1:1 ethyl acetate-hexane elution) to give 710 mg of the title compound as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated
  5. customThe crude reaction product
  6. customwas purified by flash silica gel chromatography (1:1 ethyl acetate-hexane elution)

Sources & evidence

ORD record
ord-6ad5cbefef4a4d379546e094972756db
Source dataset
uspto-grants-1993_06
Patent number
US05218115

Reaction notes

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