Butanedione → 4,5-Dimethyl-1-(3-nitrophenyl)imidazole

HRID 1835471Notes

Reaction equation

HRID 1835471 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].P(=O)(O)(O)O.[CH3:16][C:17](=O)[C:18](=O)[CH3:19].C=O.[Cl-].[NH4+:25].[C:26](=O)([O-])O.[Na+]>O>[CH3:16][C:17]1[N:25]=[CH:26][N:7]([C:6]2[CH:8]=[CH:9][CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:18]=1[CH3:19]

Participants

8

Reactant 6

HCID 650ButanedioneHCID 712FormaldehydeHCID 1004Phosphoric AcidHCID 74233-NitroanilineHCID 25517Ammonium ChlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 235036474,5-Dimethyl-1-(3-nitrophenyl)imidazoleYield 4.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of m-nitroaniline (2.0 g), phosphoric acid (1.67 ml), butane-2,3-dione (1.27 ml) and an aqueous solution of formaldehyde (35% w/w, 1.24 ml) in water (15 ml) was added an aqueous solution of ammonium chloride (5M, 6 ml) dropwise at 100° C. After stirring for 2 hours at 100° C., the mixture was poured into an aqueous saturated sodium hydrogen carbonate solution. The mixture was extracted with ethyl acetate. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified with a silica gel column chromatography eluting with 0-3% methanol/dichloromethane to give 4,5-dimethyl-1-(3-nitrophenyl)imidazole (135 mg, 4.3%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe separated organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified with a silica gel column chromatography
  6. washeluting with 0-3% methanol/dichloromethane

Sources & evidence

ORD record
ord-3a1fe0e0cf9b46539813ee48e7ae68e1
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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