Chlorine → HCID 10379727, compound

Participants

Reaction Steps

Chlorine gas was bubbled through a stirred solution of 5.00 g (17.1 mmole) of 5-n-butyl-2,4-dihydro-4-(4-nitrobenzyl)-3H-1,2,4-triazole-3-thione in 260 ml of dry CH2Cl2 for 1.5 hours. A precipitate formed after 10 minutes. (This material, which is not the desired final product, is not isolated). The reaction mixture was poured into 400 ml of ethyl acetate and washed with 3×500 ml of saturated NaHCO3 solution, 400 ml of H2O, and finally 400 ml of saturated NaCl solution. The ethyl acetate phase was dried over MgSO4, filtered, and concentrated. The residue was pre-absorbed onto silica gel by evaporation from methanol. This was added as a slurry to the top of a silica gel column, which was eluted with a gradient of 0-1% methanol in CH2Cl2. Concentration of pooled product fractions yielded 1.90 g (37%) of a yellow oil, which showed satisfactory purity by TLC in 19:1CH 2 Cl2 --MeOH and gave a positive Bellstein test for chlorine; mass spectrum (EI) m/e 294 (M+).

Provenance & Evidence