Aniline → methyl 5-(4-methoxybutyl)-2-methyl-1-phenyl-1H-imidazole-4-carboxylate

HRID 1184226Notes

Reaction equation

HRID 1184226 reaction equation
[C:1]([NH:4][CH:5]([C:10](=O)[CH2:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:6]([O:8][CH3:9])=[O:7])(=O)[CH3:2].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.FC(F)(F)C(O)=O>C(#N)CCC>[CH3:16][O:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]1[N:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:1]([CH3:2])=[N:4][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 6115AnilineHCID 6422Trifluoroacetic acidHCID 58355553Methyl 2-(acetylamino)-7-methoxy-3-oxoheptanoate

Product 1

HCID 58355289methyl 5-(4-methoxybutyl)-2-methyl-1-phenyl-1H-imidazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Procedure

Methyl 2-(acetylamino)-7-methoxy-3-oxoheptanoate (5.45 g), 5 aniline (3.01 ml) and trifluoroacetic acid (2.48 ml) were dissolved in butyronitrile (30 ml), and the reaction mixture was heated under reflux for 2 hr. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. 3.6M Aqueous potassium carbonate solution was added to the obtained residue and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (10:90-100:0) was concentrated under reduced pressure to give the object product (3.88 g).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 hr
  3. concentrationconcentrated under reduced pressure
  4. addition3.6M Aqueous potassium carbonate solution was added to the obtained residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. washa fraction eluted with ethyl acetate-hexane (10:90-100:0)
  10. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-9af817765664445a9d57c4f9134aa957
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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