Some common heterocyclic compound, 252742-72-6, name is 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one, molecular formula is C3H4ClN3O, 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 3-(Chloromethyl)-1H-1,2,4-triazol-5(4H)-one
Step 1(e): 3-chloro-5-({2-oxo-1-[(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl}oxy)benzonitrile (1-6) A suspension of the 3-chloro-5-{[2-hydroxy-4-(trifluoromethyl)pyridin-3-yl]oxy}benzonitrile (1-4; 2.00 g; 6.36 mmol), 5-(chloromethyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (1-5; 0.849 g; 6.36 mmol) and K2CO3 (0.878 g; 6.36 mmol) in DMF (32 mL) was stirred for 2 hours at room temperature, at which point LCMS analysis indicated complete conversion. The mixture was diluted with 200 mL Me-THF and washed with 150 mL 1:1:1 H2O:brine:saturated aqueous NH4Cl, then further washed with 2.x.150 mL 1:1 H2O:brine. The aqueous fractions were further extracted with 150 mL Me-THF, then the combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Purification by ISCO CombiFlash (80 g column; dry load; 100:0 to 90:10 EtOAc:EtOH over 25 minutes) provided the title compound (1-6) as a white solid. 1HNMR (400 MHz, DMSO): delta 11.46 (s, 1 H); 11.39 (s, 1 H); 7.93 (d, J=7.3 Hz, 1 H); 7.76 (s, 1 H); 7.58 (s, 1 H); 7.51 (s, 1 H); 6.67 (d, J=7.3 Hz, 1 H); 5.02 (s, 2 H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 252742-72-6, its application will become more common.
Reference:
Patent; Burch, Jason; Cote, Bernard; Nguyen, Natalie; Li, Chun Sing; St-Onge, Miguel; Gauvreau, Danny; US2011/245296; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics