Imidazole → 1-(3-Methyl-4-nitrophenyl)-1H-imidazole

HRID 1354595Notes

Reaction equation

HRID 1354595 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.[OH-].[K+].[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1>CS(C)=O>[CH3:11][C:4]1[CH:3]=[C:2]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 14797Potassium HydroxideHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 144502461-(3-Methyl-4-nitrophenyl)-1H-imidazoleYield 82.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-fluoro-2-methyl-1-nitro-benzene (300 mg, 1.84 mmol) in DMSO (2 mL) were added KOH (20 mg, 3.87 mmol) and imidazole (263 mg, 3.88 mmol). The reaction mixture was heated to 100° C. for 3.5 h, cooled to room temperature, and diluted with ice-cold water. The resulting precipitate was filtered, washed with ice-cold water, and dried under vacuum to give the title compound (310 mg, 80%) as a yellow powder. 1H NMR (300 MHz, DMSO-d6) δ 8.46 (1H, s), 8.16 (1H, d, J=8.9 Hz), 7.90–7.92 (2H, m), 7.78 (1H, dd, J=2.5, 8.9 Hz), 7.17 (1H, s), 2.61 (3H, s). LRMS (M+H)+ m/z 204.

Workup

  1. temperaturecooled to room temperature
  2. additiondiluted with ice-cold water
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with ice-cold water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-c729bac57d3d4dfcb4666ff48acffd84
Source dataset
uspto-grants-2007_05
Patent number
US07223757B2

Reaction notes

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