4-(4-CHLOROPHENYL)-5-(4-METHYLPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL synthesis
- Product Name:4-(4-CHLOROPHENYL)-5-(4-METHYLPHENYL)-4H-1,2,4-TRIAZOLE-3-THIOL
- CAS Number:451501-95-4
- Molecular formula:C15H12ClN3S
- Molecular Weight:301.79
Yield:713128-34-8 23.5%
Reaction Conditions:
with potassium carbonate in acetone at 20; for 14 h;
Steps:
5.1.1 Preparation of 2-(4-(4-chlorophenyl)-5-p-tolyl-4H-1,2,4-triazol-3-ylthio)-1-(3,4-dihydroxyphenyl)ethanone (4, XDW-1)
To a solution of the 4-(4-chlorophenyl)-5-p-tolyl-4H-1,2,4-triazole-3-thiol (3) (CAS No. 451501-95-4) (0.6g, 1.99mmol) in acetone (30mL) was added K2CO3 (0.3g, 2.17mmol) followed by 2-chloro-1-(3,4-dihydroxyphenyl)ethanone (2) (0.35g, 1.88mmol). The resulting solution was stirred at room temperature for 14h, diluted with water and extracted with EtOAc. The organic layer waswashed with water, dried on anhydrous Na2SO4, then filtered and evaporated under reduced pressure to afford white solid as crude product. Then recrystallization of the crude product in ethanol/ petroleum(60-90) gave the purified product 2-(4-(4-chlorophenyl)-5-p-tolyl-4H-1,2,4-triazol-3-ylthio)-1-(3,4-dihydroxyphenyl)ethanone (XDW-1, 4) as white solid. Yield: 0.20g, 23.5%; Rf=0.50 (petroleum 60-90/EtOAc, 1:1). 1H NMR (400MHz, DMSO-d6, ppm) δ: 9.71 (2H, brs, 2×OH), 7.62 (2H, d, J=8.6Hz), 7.46 (2H, d, J=8.7Hz), 7.44 (1H, dd, J=8.7, 2.4Hz), 7.36 (1H, d, J=2.4Hz), 7.23 (2H, d, J=8.2Hz), 7.17 (2H, d, J=8.2Hz), 6.84 (1H, d, J=8.2Hz), 4.80 (2H, s, S-CH2), 2.28 (3H, s, Me). ESI-MS: m/z 452.3 (M+1), 454.4 (M+3). C23H18ClN3O3S (451.076).
References:
Song, Yu'Ning;Lin, Xiaoqian;Kang, Dongwei;Li, Xiao;Zhan, Peng;Liu, Xinyong;Zhang, Qingzhu [European Journal of Medicinal Chemistry,2014,vol. 82,p. 293 - 307]