These common heterocyclic compound, 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 4-[1,2,4]Triazol-1-yl-benzaldehyde
A mixture of beta ionone (0.48 g, 0.507 ml, 2.5 mmol), 4-(1H-1,2,4-triazol-1-yl) benzaldehydes (0.346 g, 2 mmol), cetyltrimethyl ammonium bromide (0.028 g, 0.20 mmol), sodium hydroxide (0.240 g, 6 mmol) and water (10 ml) was stirred at room temperature for 24 h. Reaction progress was monitored by TLC and compound was extracted with ethyl acetate (2 ¡Á 30 ml). The combined organic extract was washed with water (2 ¡Á 30 ml), brine solution (25 ml), dried (Na2SO4) and the solvent was removed in vacuum. The crude product was purified by column chromatography (SiO2, 60-120 mesh). Elution with 10 % ethyl acetate in hexane furnished a yellow coloured solid (0.164 g, 24%). Mp: 103-104OC; IR (KBr, cm-1): 2929, 1643 (C=O), 1590 (C=N); 1H NMR (CDCl3, 300 MHz): delta 1.05 (s, 6 H, CH3-8? and CH3-9?), 1.41-1.45 (m, 2H, CH2-5?), 1.55-1.61 (m, 2H, CH2-4?), 1.77 (s, 3H, CH3-7?), 2.04 (t, J = 6 Hz, 2 H, H-3?), 6.42 (d, J = 16 Hz, 1H, H-4), 6.96 (d, J = 16 Hz, 1H, H-2), 7.48 (d, J = 16 Hz, 1H, H-5), 7.61 (d, J = 16 Hz, 1H, H-1), 7.67 (brs, 4H, H-2?, H-3?, H-5? and H-6?), 8.06 (s, 1H, H-3???), 8.55 (s, 1H, H-5???); 13C NMR (CDCl3, 75 MHz): delta 18.86, 21.89, 2¡Á28.87, 33.76, 34.18, 39.85, 2¡Á120.08, 126.64, 129.35, 2¡Á129.63, 134.87, 136.50, 137.26, 137.89, 140.69, 140.82, 143.54, 152.78, 188.66; ESI-MS m/z: 348 [M+1]+; Analysis calculated for C22H25N3O: C, 76.05; H, 7.25; N, 12.09; Found: C, 76.10; H, 7.19; N, 12.11.
The synthetic route of 4-[1,2,4]Triazol-1-yl-benzaldehyde has been constantly updated, and we look forward to future research findings.
Reference:
Article; Suryawanshi; Tiwari, Avinash; Kumar, Santosh; Shivahare, Rahul; Mittal, Monika; Kant, Padam; Gupta, Suman; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 2925 – 2928;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics