Diethyl Ether → HCID 20141783, compound

Participants

Reaction Steps

Methyllithium (219 cm3 of a 1.5M solution in ether) was added dropwise to a stirred suspension of 1-(4-amino-3-methylphenyl)-5-cyano-2,4-dimethylimidazole (9.3 g) in ether (100 cm3) at -70° under nitrogen. The mixture was allowed to warm to room temperature over 1 hour and then heated under reflux for 5 hours. The mixture was quenched by the dropwise addition of water (50 cm3), acidified with 2M hydrochloric acid (50 cm3), and warmed on a steam bath for 5 minutes. The mixture was basified with 10% sodium carbonate solution to pH9 and extracted with dichloromethane (3×200 cm3). The combined and dried (MgSO4) organic extracts were evaporated in vacuo to give a residue which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]). Elution of the column with hexane:ethyl acetate, 1:1, gave firstly fractions containing recovered starting material (2.9 g). Further elution with hexane:ethyl acetate, 1:4, followed by combination and evaporation of the appropriate fractions, afforded the title compound as an oil (5.6 g), which was used (Preparation 11) without further purification.

Provenance & Evidence