Tetrahydrofuran → HCID 10098027, compound

Participants

Reaction Steps

A solution of 450 mg (1.16 mmole) of 4-(4- aminobenzyl)-3-n-butyl-5-(4-chlorobenzylthio)-4H-1,2,4-triazole (Step B), 438 μl (325 mg, 2.52 mmole) of N,N-diisopropylethylamine and 418 mg (2.53 mmole) of 2-cyanobenzyl chloride [R. Scholl and W. Neuberger, Monatsh. Chem. 33, 507 (1911)] in 10 ml of dry THF was stirred overnight at room temperature under N2. The mixture was filtered, and the filtrate was concentrated in vacuo. The residue was dissolved in 50 ml of ethyl acetate and washed with 2×60 ml of saturated NaHCO3 solution followed by 50 ml of saturated NACl. The organic phase was then dried (MgSO4), filtered, and concentrated. A solution of the residue in CH2Cl2 was treated with approximately 2 g of silica gel, and the mixture was evaporated to give a dry powder, which was added as a slurry in hexane to the top of a silica gel column packed in the same solvent. The column was eluted briefly with hexane and then with a stepwise gradient from 1:1 hexane-EtOAc to 100% EtOAc. Two major products were eluted, the second of which correspond to the desired product. Fractions containing this material were combined and concentrated to give 229 mg (36%) of the title compound as a solid, mp 75°-77° C. dec., homogeneous by TLC in 1:3 hexane-EtOAc; mass spectrum (FAB) m/e 516 (M+1)+.

Provenance & Evidence