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

HRID 2420772Notes

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-d57978f860cd4529b5b819b30f43ee27
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07956053B2

Reaction notes

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