Acetic Acid → 4-methyl-1-(3-nitrophenyl)-1H-imidazole

HRID 1835477Notes

Reaction equation

HRID 1835477 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]([CH2:13][C:14](=O)[CH3:15])[CH:11]=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C([O-])(=O)C.[NH4+:21].C(O)(=O)C>C1(C)C(C)=CC=CC=1>[CH3:15][C:14]1[N:21]=[CH:11][N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 517165Ammonium AcetateHCID 23503669N-(3-nitrophenyl)-N-(2-oxo-propyl)-formamide

Product 1

HCID 150301664-methyl-1-(3-nitrophenyl)-1H-imidazoleYield 83.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A suspension of N-(3-nitrophenyl)-N-(2-oxo-propyl)-formamide (265 mg), ammonium acetate (919 mg) and acetic acid (0.3 ml) in xylene (5 ml) was refluxed for 2.5 hours and then evaporated under reduced pressure. To the residue were added ethyl acetate and an aqueous solution of sodium hydroxide (1N, 25 ml), and the mixture was stirred for 10 minutes. The separated organic layer was washed with water and brine, dried over magnesium sulfate and evaporated to give 4-methyl-1-(3-nitrophenyl)imidazole (203 mg, 83.9%).

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. customevaporated under reduced pressure
  3. additionTo the residue were added ethyl acetate
  4. washThe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-1c5c924e2e034c0295c02e79a42132ed
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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