alpha-Bromo-o-chlorotoluene → HCID 59006446, compound

Participants

Reaction Steps

Sodium hydride (55%, 24 mg) was added to a THF (10 ml) solution of 5-[1-(3-chloro-4-methyl-2-thienyl)cyclopentyl]-4-methyl-2,4-dihydro-3H-1,2,4-triazol-3-thione (154 mg) at 0° C. and the whole was stirred for 5 minutes. Then, 2-chlorobenzyl bromide (0.07 ml) was added thereto, followed by stirring at 0° C. for 3 hours. The reaction solution and chloroform were added to a saturated aqueous sodium hydrogen carbonate solution and then the organic layer was separated. Furthermore, the organic layer washed with brine, dried over anhydrous sodium sulfate, and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by column chromatography (hexane:ethyl acetate=1:1) to obtain 200 mg of 3-[(2-chlorobenzyl)thio]-5-[1-(3-chloro-4-methyl-2-thienyl)cyclopentyl]-4-methyl-4H-1,2,4-triazole (pale yellow foam). It was converted into an ethyl acetate (5 ml) solution and 4M hydrogen chloride-ethyl acetate (0.23 ml) was added, followed by removal of the solvent by evaporation under reduced pressure. The resulting solid washed with ether to obtain 185 mg of 3-[(2-chlorobenzyl)thio]-5-[1-(3-chloro-4-methyl-2-thienyl)cyclopentyl]-4-methyl-4H-1,2,4-triazole hydrochloride (colorless solid).

Provenance & Evidence