4-Fluorophenyl isocyanate → 1-(4-[2-[4-(2,4-Dioxothiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazol-6-yloxy]phenyl)-1-n-hexyl-3-(4-fluorophenyl)urea

Participants

Reaction Steps

A mixture of 5-[4-[6-(4-n-hexylaminophenoxy)-1-methyl-1H-benzimidazol-2-ylmethoxy]benzyl]thiazolidine-2,4-dione (0.39 g), 4-fluorophenyl isocyanate (0.11 g) and anhydrous tetrahydrofuran (20 ml) was allowed to stand at room temperature for 2 days. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=3:2 as the eluant and the product was reprecipitated from a mixture of ethyl acetate and diisopropyl ether to afford the title compound (0.32 g, Rf=0.45: thin layer chromatography on a silica gel plate using ethyl acetate:n-hexane=2:1 as the eluant).

Provenance & Evidence