Aniline → methyl 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylate

HRID 1428989Notes

Reaction equation

HRID 1428989 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH:4]([NH:8][C:9](=O)[CH3:10])[C:5](=O)[CH3:6].[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.FC(F)(F)C(O)=O>C(#N)CCC>[CH3:10][C:9]1[N:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:5]([CH3:6])=[C:4]([C:3]([O:2][CH3:1])=[O:12])[N:8]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 6422Trifluoroacetic acidHCID 11084356Methyl 2-acetamido-3-oxobutanoate

Product 1

HCID 14003955methyl 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylateYield 46%

Reagents, catalysts & solvents 1

HCID 8008ButyronitrileSolvent

Procedure

Part C: To a magnetically stirred solution of 2-acetylamino-3-oxo-butyric acid methyl ester (5 gram, 28.9 mmol) in butyronitrile was added aniline (3.42 ml) and trifluoroacetic acid (2.89 ml) and the resulting mixture was heated at reflux for 45 minutes. The butyronitrile was removed in vacuo at room temperature and the resulting residues was taken up dichloromethane and washed twice with an aqueous potassium carbonate solution. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified by flash chromatography (diethyl ether/acetone=4/1 (v/v)) to give methyl 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylate (3.0 gram, 46% yield). 1H-NMR (400 MHz, CDCl3): 2.22 (s, 3H), 2.33 (s, 3H), 3.91 (s, 3H), 7.18-7.22 (m, 2H), 7.51-7.59 (m, 3H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 45 minutes
  3. customThe butyronitrile was removed in vacuo at room temperature
  4. washwashed twice with an aqueous potassium carbonate solution
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by flash chromatography (diethyl ether/acetone=4/1 (v/v))

Sources & evidence

ORD record
ord-ca9562fb5275471095917e066ade6b2f
Source dataset
uspto-grants-2015_01
Patent number
US08937184B2

Reaction notes

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