1,3-di(tetrazol-5-yl)propane synthesis

Yield:26670-17-7 96%

Reaction Conditions:

with sodium azide;triethylamine hydrochloride in toluene at 100 - 110; for 20 h;

Steps:

2.2.1. 1,3-Di(1H-tetrazol-5-yl)propane (1)

Triethylammonium chloride (68.8 g, 0.5 mol) and sodium azide(32.5 g, 0.5 mol) were added to a solution of glutaronitrile (21.6 g,0.23 mol) in toluene (300 ml), and the mixture was stirred at100-110 C for 20 h. After cooling the reaction mixture to roomtemperature, distilled water (250 ml) was added, the aqueous layerwas separated and the toluene layer was washed with water(3 50 ml). The joint aqueous layers were acidified to pH 2 using conc. hydrochloric acid. The precipitate that formed was filteredoff, washed with water and dried in a vacuum oven, giving a whitepowder. Yield: 96% (39.8 g, 0.22 mol). Mp: 205-210 C (Lit. 198 C[32]). 1H NMR (500 MHz, CD3CN) d, ppm: 2.25 (quintet, 2H, CH2),2.95 (t, 4H, 2 CH2). 13C NMR (125 MHz, CD3CN) d, ppm: 23.3,27.5, 155.4 (Cring).

References:

Grigoriev, Yuri V.;Ivashkevich, Ludmila S.;Ivashkevich, Oleg A.;Kersting, Berthold;Klose, Jennifer;Lyakhov, Alexander S.;Shiman, Dmitriy I.;Voitekhovich, Sergei V. [Polyhedron,2020,vol. 190,art. no. 114793]