Imidazole → 1-(4-Methyl-2-nitrophenyl)-1H-imidazole

HRID 1445435Notes

Reaction equation

HRID 1445435 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1>CN(C=O)C>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 1362874-Fluoro-3-nitrotoluene

Product 1

HCID 153886721-(4-Methyl-2-nitrophenyl)-1H-imidazoleYield 75.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

4-fluoro-3-nitro-toluene (346 mg, 2.2 mmol) and imidazole (299 mg, 4.4 mmol) was dissolved in DMF (5 mL) and the reaction heated to 90° C. for 16 h. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and 1 M HCl (aq). The aqueous layer was separated and basified with NaOH (s) and extracted with DCM. The DCM was concentrated in vacuo and the residue purified by flash chromatography (Silica, EtOAc:Heptane) to afford the title compound (337 mg, 75%). LC/MS: (00-60% B in A): tR=1.69 min, >90%, m/z (ESI)=204 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between ethyl acetate and 1 M HCl (aq)
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM
  5. concentrationThe DCM was concentrated in vacuo
  6. customthe residue purified by flash chromatography (Silica, EtOAc:Heptane)

Sources & evidence

ORD record
ord-15500b37989146198eb999aa93392e36
Source dataset
uspto-grants-2010_02
Patent number
US07666834B2

Reaction notes

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