Potassium Carbonate → 2-Ethyl-1-(2-nitro-5-fluorophenyl)-4-methyl-1H-imidazole

HRID 374095Notes

Reaction equation

HRID 374095 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12]([C:14]1[NH:15][CH:16]=[C:17]([CH3:19])[N:18]=1)[CH3:13].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:12]([C:14]1[N:15]([C:2]2[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=2[N+:9]([O-:11])=[O:10])[CH:16]=[C:17]([CH3:19])[N:18]=1)[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679672,4-DifluoronitrobenzeneHCID 178437635HCID 178437635, compound

Product 1

HCID 150765552-Ethyl-1-(2-nitro-5-fluorophenyl)-4-methyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Combine 100 g of 2,4-difluoronitrobenzene, 69 g of 2-ethyl-4-methylimidazole and 100 g of K2CO3 in 700 mL of acetonitrile, and stir at room temperature for 4 days. Remove the solvent under vacuum. Slurry the residue in 300 mL of CH2Cl2 and chromatograph over 1 kg of silica gel using CH2Cl2. Combine the appropriate fractions and remove the solvent under vacuum. Crystallize the residue from pet ether to provide the title compound.

Workup

  1. customRemove the solvent under vacuum
  2. customremove the solvent under vacuum
  3. customCrystallize the residue from pet ether

Sources & evidence

ORD record
ord-71805efd4d9e45e782272370cca5ac0d
Source dataset
uspto-grants-1992_11
Patent number
US05166344

Reaction notes

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