Ethyl Acetate → HCID 67424079, compound

HRID 1930548Notes

Reaction equation

HRID 1930548 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[O:17][CH3:18].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.ClCCl.CCCCCC>[CH3:18][O:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1.[CH3:18][O:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:3]1[C:2]([CH3:1])=[CH:6][N:5]=[CH:4]1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 144519681-Fluoro-2-methoxy-4-nitrobenzeneHCID 178418800HCID 178418800, compound

Product 2

HCID 454801801-(2-methoxy-4-nitrophenyl)-4-methyl-1H-imidazoleHCID 67424079HCID 67424079, compoundYield 83.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 4-methyl imidazole (500 mg, 6 mmol), 2-fluoro-5-nitro anisole (1.02 g, 5.9 mmol) and potassium carbonate (1.68 g, 12 mmol) in DMF (15 mL) was heated overnight at 85° C. in a sealed tube. The reaction mixture was cooled, transferred into a round bottom flask using ethyl acetate and concentrated under high vacuum to 5 mL volume. The residue was suspended in water and extracted with dichloromethane (3×25 mL). The organic extracts were combined, washed with brine, dried over anhydrous MgSO4, filtered and concentrated to give an orange solid. The solid was dissolved in dichloromethane (10 mL) and diluted with hexane until the solution became slightly turbid. The turbid solution was left at room temperature. The separated orange solid was filtered, washed with hexane to give 1-(2-methoxy-4-nitro-phenyl)-4-methyl-1H-imidazole and 1-(2-methoxy-4-nitro-phenyl)-5-methyl-1H-imidazole (577 mg, 43%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customtransferred into a round bottom flask
  3. concentrationconcentrated under high vacuum to 5 mL volume
  4. extractionextracted with dichloromethane (3×25 mL)
  5. washwashed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give an orange solid
  10. waitThe turbid solution was left at room temperature
  11. filtrationThe separated orange solid was filtered
  12. washwashed with hexane

Sources & evidence

ORD record
ord-660190258d374e91b91c45adc59c4b61
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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