2-Methylimidazole → 3-(2-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)-benzonitrile

HRID 1375605Notes

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]=1

Participants

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-a8292033fc4b4dc1bcc3fae7e2e25175
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07169791B2

Reaction notes

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