2-Methylimidazole → 3-(2-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)-benzonitrile
Reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[C:5]#[N:6].[CH3:14][C:15]1[NH:16][CH:17]=[CH:18][N:19]=1>CN(C)C(=O)C>[CH3:14][C:15]1[N:16]([C:2]2[CH:3]=[C:4]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=2)[C:5]#[N:6])[CH:17]=[CH:18][N:19]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 145 °C
Procedure
A mixture of 3-fluoro-5-(trifluoromethyl)-benzonitrile (Lancaster Synthesis GmbH; 17 g, 89 mmol) and 2-methylimidazole (Fluka, Buchs, Switzerland; 22.2 g, 270 mmol) in N,N-dimethylacetamide (80 mL) is stirred at 145° C. for 19 h. The solvent is evaporated off under reduced pressure and the residue is dissolved in ethyl acetate (200 mL). The solution is washed with brine (200 mL), dried (Na2SO4) and the solvent is evaporated off under reduced pressure to give the crude product which is purified by recrystallisation from ether—hexane to afford the title compound as yellow crystalline solid, m.p. 132-134° C.
Workup
- customThe solvent is evaporated off under reduced pressure
- dissolutionthe residue is dissolved in ethyl acetate (200 mL)
- washThe solution is washed with brine (200 mL)
- dry with materialdried (Na2SO4)
- customthe solvent is evaporated off under reduced pressure
- customto give the crude product which
- customis purified by recrystallisation from ether—hexane
Sources & evidence
- ORD record
- ord-319d93f8cd3548c0b4a89973d4b1207b
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07569566B2
Reaction notes
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