Carbon Disulfide → HCID 178527924, compound

Participants

Reaction Steps

To a suspension of (6-chloro-pyridazin-3-yl)-hydrazine (1 g, 6.917 mmol) in ethanol (12 mL) was added a solution of KOH (390 mg, 6.917 mmol) in water (12 mL) dropwise. Carbon disulfide (0.84 mL, 13.84 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 48 h. Another 0.84 mL CS2 and 390 mg KOH were added, and the reaction mixture was further stirred for 24 h, before concentrating in vacuo. The residue was treated with 1 M aqueous NaOH and filtered. The filtrate was acidified to pH 3 with 1 N aqueous HCl, and the precipitate was filtered off. The resulting filtrate was extracted with ethyl acetate (3×), and the combined organics were dried over sodium sulfate, filtered, concentrated and dried in vacuo to provide 485 mg of 6-chloro-[1,2,4]triazolo[4,3-b]pyridazine-3-thiol as a yellow solid (38% yield): 1H NMR (DMSO-d6): δ 7.48 (d, 1H), 8.24 (d, 1H); MS (m/z) 187 [M+H+]+.

Provenance & Evidence