Nitric Acid → HCID 86724374, compound

HRID 1754368Notes

Reaction equation

HRID 1754368 reaction equation
C(OC(=O)C)(=O)C.[CH3:8][C:9]1[NH:13][CH:12]=[N:11][C:10]=1[N+:14]([O-:16])=[O:15].[N+]([O-])(O)=O.[F:21][C:22]1[CH:28]=[CH:27][C:25](N)=[CH:24][CH:23]=1>O.CO>[CH3:8][C:9]1[N:13]([C:25]2[CH:27]=[CH:28][C:22]([F:21])=[CH:23][CH:24]=2)[CH:12]=[N:11][C:10]=1[N+:14]([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 97314-FluoroanilineHCID 178433696HCID 178433696, compound

Product 1

HCID 86724374HCID 86724374, compoundYield 43.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Acetic anhydride (1.65 mL) was added to 5-methyl-4-nitro-1H-imidazole (254 mg, 2.00 mmol) at room temperature. Nitric acid (70%, 200 μL) was added and the reaction was stirred for three days. The reaction was then poured onto ice. The product was extracted with dichloromethane three times. The combined organic layers was washed with saturated sodium bicarbonate solution and dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the crude 5-methyl-1,4-dinitro-1H-imidazole (235 mg) was dissolved in methanol (3 mL) at ambient temperature. A methanol (0.8 mL) solution of 4-fluoroaniline (157 μL, 1.63 mmol) was added dropwise and the reaction was stirred at this temperature for five days. Water was added to the reaction mixture and the product was extracted with dichloromethane three times. The combined organic layers were dried over anhydrous sodium sulfate. After removal of solvent under reduced pressure, the crude material was purified using silica gel column chromatography (33-60% ethyl acetate in hexanes) to give 5-methyl-4-nitro-1-(4-fluorophenyl)-1H-imidazole (157 mg, 0.712 mmol, 36% yield over two steps).

Workup

  1. additionThe reaction was then poured onto ice
  2. extractionThe product was extracted with dichloromethane three times
  3. washThe combined organic layers was washed with saturated sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removal of the solvent under reduced pressure
  6. dissolutionthe crude 5-methyl-1,4-dinitro-1H-imidazole (235 mg) was dissolved in methanol (3 mL) at ambient temperature
  7. stirringthe reaction was stirred at this temperature for five days
  8. extractionthe product was extracted with dichloromethane three times
  9. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  10. customAfter removal of solvent under reduced pressure
  11. customthe crude material was purified

Sources & evidence

ORD record
ord-528a769b80ad4ca6a48824d0074006ae
Source dataset
uspto-grants-2015_10
Patent number
US09169248B2

Reaction notes

Loading…