Some common heterocyclic compound, 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine, molecular formula is C3H6N4, 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. Formula: C3H6N4
General procedure: 3-Amino-1,2,4-triazole 8a-f (1.0 mmol), o-hydroxybenzaldehyde9a-e (1.0 mmol), acetone (10) (0.22 ml,3.0 mmol), and abs. EtOH (2 ml) were mixed in amicrowave process vial, and then 4 N solution of HCl indioxane (0.07 ml, 0.3 mmol) was added. The mixture wasirradiated at 150C for 30 min. The reaction mixture wascooled by an air flow and stirred for 24 h at roomtemperature for complete precipitation of the product. Theprecipitate was filtered off, washed with EtOH (1 ml) andEt2O (3¡Á1 ml), and dried. Compounds 1a-w were obtainedin a form of white solids.2,5-Dimethyl-11,12-dihydro-5,11-methano[1,2,4]triazolo[1,5-c][1,3,5]benzoxadiazocine (11a). Yield 48%,mp 310-311C. IR spectrum, nu, cm-1: 757, 1091, 1138,1325, 1485, 1548, 1625, 2885, 2922, 3070, 3421. 1H NMRspectrum, delta, ppm: 7.76 (1H, s, NH); 7.33-7.26 (1H, m,H Ar); 7.20-7.12 (1H, m, H Ar); 6.98-6.90 (1H, m, H Ar);6.82-6.76 (1H, m, H Ar); 4.52 (1H, s, 11-CH); 2.30 (2H, s,13-CH2); 2.02 (3H, s, 2-CH3); 1.91 (3H, s, 5-CH3).13C NMR spectrum, delta, ppm: 157.3 (C); 153.9 (C); 151.0(C); 130.0 (CH); 129.4 (CH); 124.4 (C); 121.2 (CH); 116.7(CH); 82.3 (C); 44.3 (CH); 32.3 (CH2); 24.0 (CH3); 14.2(CH3). Mass spectrum, m/z: 242 [M]+. Found, %: C 64.34;H 5.54; N 23.29. C13H14N4O. Calculated, %: C 64.45;H 5.82; N 23.12.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4923-01-7, its application will become more common.
Reference:
Article; Guemue?, Mustafa K.; Gorobets, Nikolay Yu.; Sedash, Yuriy V.; Chebanov, Valentin A.; Desenko, Sergey M.; Chemistry of Heterocyclic Compounds; vol. 53; 11; (2017); p. 1261 – 1267; Khim. Geterotsikl. Soedin.; vol. 53; 11; (2017); p. 1261 – 1267,7;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics