Sodium Iodide → 1-But-3-ynyl-1H-[1,2,3]triazole

Participants

Reaction Steps

A suspension of NaOH (37.86 g, 946.5 mmol), sodium iodide (94.65 g, 631.5 mmol) and 1H-[1,2,3]triazole (61.03 g, 883.6 mmol) in 2-methyl-2-butanol (750 mL) was refluxed for 1 h under an inert atmosphere. After cooling to room temperature the methane sulfonate (94.18 g, 631.2 mmol) was added within 5 minutes. The resulting suspension was then heated to reflux for 3 h, cooled to room temperature and concentrated in vacuo at 45° C. Water (500 mL) and dichloro methane (1 L) were added and the organic phase was separated, dried over sodium sulfate and the volatiles removed at 30° C. The residue was distilled at 1 mmHg. A forerun was collected at 20–70° C. The main fraction distilled at 123–129° C. as a colorless, turbid liquid. After filtration over Celite 1-but-3-ynyl-1H-[1,2,3]triazole was obtained as a colorless liquid (29.77 g, 38.9%).

Provenance & Evidence