Water → 4-Iodo-2-methyl-1-(3-methyl-4-nitrophenyl)-1H-imidazole

HRID 649542Notes

Reaction equation

HRID 649542 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=1.[I:12][C:13]1[N:14]=[C:15]([CH3:18])[NH:16][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[I:12][C:13]1[N:14]=[C:15]([CH3:18])[N:16]([C:2]2[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH3:8])[CH:7]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 949565-Fluoro-2-nitrotolueneHCID 178433060HCID 178433060, compound

Product 1

HCID 198670994-Iodo-2-methyl-1-(3-methyl-4-nitrophenyl)-1H-imidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-fluoro-2-nitrotoluene (7.9 g), 4-iodo-2-methylimidazole (9.0 g) and sodium carbonate (4.5 g) was heated with stirring in dimethylformamide (50 cm3) at 120° for 16 hours under nitrogen. The mixture was poured into water (50 cm3) and extracted with chloroform (3×100 cm3). The combined and dried (MgSO4) organic extracts were concentrated in vacuo to give a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with ethyl acetate:toluene, 1:5 by volume. Combination and evaporation of appropriate fractions afforded a solid which was recrystallised from dichloromethane-hexane to give the title compound, m.p. 146°-8°, (4.0 g).

Workup

  1. temperaturewas heated
  2. extractionextracted with chloroform (3×100 cm3)
  3. dry with materialdried (MgSO4) organic extracts
  4. concentrationwere concentrated in vacuo
  5. customto give a solid which
  6. customwas chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  7. washeluting with ethyl acetate
  8. customCombination and evaporation of appropriate fractions
  9. customafforded a solid which
  10. customwas recrystallised from dichloromethane-hexane

Sources & evidence

ORD record
ord-c72c938b0d074c4aa6176c102f341c5d
Source dataset
uspto-grants-1988_04
Patent number
US04740513

Reaction notes

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