Potassium Carbonate → 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

HRID 1783464Notes

Reaction equation

HRID 1783464 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[C:6](Br)[CH:7]=1.[CH3:13][C:14]1[N:15]=[CH:16][NH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C>C(OCC)(=O)C>[CH3:13][C:14]1[N:15]=[CH:16][N:17]([C:6]2[CH:7]=[C:2]([NH2:1])[CH:3]=[C:4]([C:9]([F:12])([F:10])[F:11])[CH:5]=2)[CH:18]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 27358803-Bromo-5-(trifluoromethyl)anilineHCID 178418800HCID 178418800, compound

Product 1

HCID 120028253-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-amino-5-bromo-benzotrifluoride (17.1 g, 71.24 mmol), 4-methylimidazole (17.6 g, 213.72 mmol), potassium carbonate (9.8 g, 71.24 mmol), cupper (1.1 g, 17.81 mmol), and cupper iode (II) (3.4 g, 17.81 mmol) were added to N,N-dimethylacetamide (100 ml) at room temperature, and mixed therewith at 140˜150° C. for 16 hr. After the reaction was completed, the temperature of the reaction vessel was cooled to RT. Then, ethyl acetate (200 ml) was added thereto and mixed therewith for 30 min. The reaction mixture was filtered with Celite, and an organic layer of the filtered solution was washed with water, dried with magnesium sulfate, distilled under vacuum, and washed with n-hexane to give the titled compound as pale white solid.

Workup

  1. additionmixed
  2. additionmixed
  3. waitfor 30 min
  4. filtrationThe reaction mixture was filtered with Celite
  5. washan organic layer of the filtered solution was washed with water
  6. dry with materialdried with magnesium sulfate
  7. distillationdistilled under vacuum
  8. washwashed with n-hexane

Sources & evidence

ORD record
ord-2a51e84d22ac42abaf14a4270c721b0e
Source dataset
uspto-grants-2009_03
Patent number
US07501424B2

Reaction notes

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