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

HRID 1051264Notes

Reaction equation

HRID 1051264 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].CC(N(C)C)=O.[CH3:19][C:20]1[N:21]=[CH:22][NH:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C.[Cu]I>[CH3:19][C:20]1[N:21]=[CH:22][N:23]([C:2]2[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=2)[NH2:5])[CH:24]=1

Participants

7

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)anilineYield 67%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

3-Bromo-5-(trifluoromethyl)aniline (0.2 mL, 1.43 mmol) was stirred in a solvent of dimethylacetamide (10 mL). The reaction solution was added with 4-methyl-1H-imidazole (0.35 g, 4.26 mmol), K2CO3 (0.20 g, 5.23 mmol), Cu (0.022 g, 0.346 mmol) and CuI (0.068 g, 0.115 mmol), and stirred for about 2 days at 140° C. The reaction mixture was diluted with ethyl acetate, and washed with a saturated aqueous sodium bicarbonate solution and saline. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (0.23 g, 67%).

Workup

  1. washwashed with a saturated aqueous sodium bicarbonate solution and saline
  2. customThe organic layer thus obtained
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e83cd808f5a04f0ba438a9b00630c151
Source dataset
uspto-grants-2016_07
Patent number
US09388165B2

Reaction notes

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