Sodium hydride → HCID 86735282, compound

Participants

Reaction Steps

A solution of 1-(5-chloro-2-thienyl)-2-(1-imidazolyl) ethanol (1.1 g, 4.8 mmole) dissolved in dry tetrahydrofuran (10 ml) was added to a stirred suspension of sodium hydride (0.4 g, as 80% dispersion in oil, 16 mmole) in dry tetrahydrofuran (40 ml). After stirring for 1 hour at room temperature the mixture was cooled in ice and a solution of 2-bromomethyl-3-chloro-thiophene (1.0 g, 4.7 mmole) in dry tetrahydrofuran (10 ml) was added dropwise. The mixture was allowed to stir for a further 1 hour at 15° C and the solvent then removed under vacuum. The residue was extracted several times with diethyl ether and the etheral extracts were combined and evaporated. The residue was taken up in a little diethyl ether and treated with a solution of hydrogen chloride in diethyl ether to precipitate a gum which solidified on trituration with acetone and ether. Recrystallization from a mixture of acetone, methanol and diisopropyl ether gave 1-[2-(5 -chloro-2-thienyl)-2-(3-chloro-2-thienyl methoxy)ethyl]imidazole hydrochloride as a white solid (0.5 g, 32%) m.p. 120°-121° C. (Found: C, 41.6; H, 3.35; N, 6.9. C14H12N2Cl2OS2. HCl requires C, 42.5; H, 3.3; N, 7.1%).

Provenance & Evidence