1-Chloro-4-(chloromethyl)benzene → 1-(4-chlorobenzyl)-1H-1,2,4-triazol-3-amine

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Reaction Steps

Sodium metal (460 mg, 20 mmol) was dissolved in 30 ml of methanol and 3-amino-1,2,4-triazole (1.682 g, 20 mmol) added. The resulting clear solution was stirred for 1 hour at room temperature, evaporated to dryness and the sodium salt suspended in 45 ml DMF. A solution of 4-chlorobenzyl chloride (3.221 g, 20 mmol) in 5 ml DMF was slowly added to the heavily stirred suspension obtained previously. After 3 hours at room temperature, a cloudy solution was obtained, which was stirred overnight at 20° C. The resulting mixture was concentrated in the rotatory evaporator and the oily residue treated with 100 ml of dichloromethane. Insoluble material was filtered off and the filtrate concentrated to give a brownish oil which solidified on standing. Chromatography on silica gel using dichloromethane/methanol 98:2 v/v as an eluent gave a poor separation of the two regioisomers. However, a pure fraction (215 mg, 5%) of the title compound could be obtained as a colorless solid after trituration with diethyl ether. MS ISP (m/e): 209.0 & 211.0 (100 & 43) [(M+H)+].

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