2-(4-((2-Butyl-4-chloro-5-formylimidazol-1-yl)methyl)phenyl)benzonitrile → HCID 178441683, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.11 g of 2-butyl-4-chloro-5-formyl-1-(2'-cyanobiphenyl-4-yl)methylimidazole, 8.38 g of trioctyltin azide (tri-n-octyltin azide) and 10 ml of toluene was stirred at 120° C. for 18 hours. After cooling, the reaction mixture was concentrated. To the residue was added 10 ml of ethanol as well as an aqueous solution of sodium nitrite (1.3 g/5 ml) and the mixture was adjusted to pH 3.3 with concentrated hydrochloric acid. The mixture was diluted with 20 ml of water and extracted with two 20 ml portions of ethyl acetate. The ethyl acetate solution was concentrated and the residue was purified by chromatography on 30 g of silica gel (CH2Cl2 -MeOH). The active fraction was concentrated to provide 1.82 g of 2-butyl-4-chloro-5-formyl-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methylimidazole. Yield 73%. 1H NMR (CDCl3) δ: 0.78-1.80 (9H), 2.53 (3H, t), 5.51 (2H, s), 6.9-8.0 (12H, m), 9.66 (1H, s) IR(KBr): 2964, 1668, 1518, 1466, 1382, 1280, 758 cm-1

Provenance & Evidence