1-Bromo-3-chloropropane → 5-(5-[(3-chloropropyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl)-2-methylquinoline

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (2.65 g, 60% in oil) was added portionwise to stirred absolute ethanole at 0° C., under a nitrogen atmosphere. Then 4-methyl-5-(2-methyl-5-quinolinyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (21.8 g) (intermediate 7) was added portionwise and the reaction mixture was allowed to reach room temperature. Then 1-bromo-3-chloropropane (12.6 ml) was added over 10 min and the reaction mixture was brought to 80° C. and left to react an additional hour after which time the reaction mixture was allowed to reach room temperature and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel with 90% ethyl acetate-acetone to give the title compound (14.18 g) as a white solid.

Provenance & Evidence