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

HRID 1835474Notes

Reaction equation

HRID 1835474 reaction equation
[CH3:1][CH:2]([N:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH:7]=O)[C:3](=O)[CH3:4].C([O-])(=O)C.[NH4+:22].C(O)(=O)C.[OH-].[Na+]>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[CH3:4][C:3]1[N:22]=[CH:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 517165Ammonium AcetateHCID 23503659N-(1-methyl-2-oxo-propyl)-N-(3-nitrophenyl)formamide

Product 1

HCID 235036474,5-Dimethyl-1-(3-nitrophenyl)imidazoleYield 73.4%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of N-(1-methyl-2-oxo-propyl)-N-(3-nitrophenyl)formamide (1.17 g), ammonium acetate (3.82 g) and acetic acid (1 ml) in xylene (20 ml) was refluxed for 2 hours. After adding ethyl acetate and an aqueous solution of sodium hydroxide (1N, 100 ml), the mixture was stirred for 10 minutes. The separated aqueous layer was extracted with ethyl acetate. The combined organic layers were 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 1-3% unethanol/dichloromethane to give 4,5-dimethyl-1-(3-nitrophenyl)imidazole (0.79 g, 73.1%).

Workup

  1. temperaturewas refluxed for 2 hours
  2. extractionThe separated aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified with a silica gel column chromatography
  7. washeluting with 1-3% unethanol/dichloromethane

Sources & evidence

ORD record
ord-7850bd0863fc47e4ba0fa9ec4933ede5
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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