Propargyl bromide → HCID 178460803, compound

Participants

Reaction Steps

To a solution of 21.8 g of potassium hydroxide in 400 ml of methanol under nitrogen was added 33.37 g of 1,2,4-triazole-3-thiol. The resulting mixture was stirred at ambient temperature for ~1 hour. To this mixture was added 33.4 ml of propargyl bromide dropwise while keeping the reaction temperature below 30° C. After the addition, the resulting mixture was stirred at ambient temperature for ~4 hours and was then concentrated under reduced pressure. The residue was triturated in 300 ml of water. The precipitate was collected by filtration, washed with water and then hexanes, air dried and then dried in oven to give 24.6 g of the title product as a solid, m.p. 102°-104° C. NMR (DMSO-d6): 3.14 (t, 1H); 3.92 (d, 2H); 8.48 (s, 1H); 14.2 (bs, 1H).

Provenance & Evidence