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

HRID 568378Notes

Reaction equation

HRID 568378 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.[NH:12]1[CH:16]=[CH:15][N:14]=[CH:13]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:11][C:4]1[CH:3]=[C:2]([N:12]2[CH:16]=[CH:15][N:14]=[CH:13]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 10340Sodium CarbonateHCID 949565-Fluoro-2-nitrotoluene

Product 1

HCID 144502461-(3-Methyl-4-nitrophenyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-fluoro-2-methylnitrobenzene (15.5 g), imidazole (6.8 g), and sodium carbonate (11.1 g) was heated at 100° for 24 hours in dimethylformamide (DMF). The mixture was then concentrated in vacuo, the residue was acidified to pH1 with 4M hydrochloric acid, and the resulting solution was extracted with chloroform (2×25 cm3). The aqueous phase was basified to pH10 with 2.5M sodium hydroxide solution and the mixture was extracted with chloroform (3×100 cm3). The dried (MgSO4) organic extracts were evaporated to give a solid which was recrystallised from ethyl acetate to afford 1-(3-methyl-4-nitrophenyl)imidazole, m.p. 112°-115°, (10.0 g).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. extractionthe resulting solution was extracted with chloroform (2×25 cm3)
  3. extractionthe mixture was extracted with chloroform (3×100 cm3)
  4. dry with materialThe dried (MgSO4) organic extracts
  5. customwere evaporated
  6. customto give a solid which
  7. customwas recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-78b1f21e79954137bcfc563a7ff9137a
Source dataset
uspto-grants-1988_03
Patent number
US04728653

Reaction notes

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