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

HRID 345001Notes

Reaction equation

HRID 345001 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-1a92986e04664143a75c129ce6cb4ef2
Source dataset
uspto-grants-1991_10
Patent number
US05055465

Reaction notes

Loading…