2,4-Triazole-3-thione,2,4-dihydro-5-methyl-4-phenyl-3H-1 synthesis

7synthesis methods

Product Name:2,4-Triazole-3-thione,2,4-dihydro-5-methyl-4-phenyl-3H-1
CAS Number:6232-82-2
Molecular formula:C9H9N3S
Molecular Weight:191.25

13153-00-9
3 suppliers
$106.00/50MG

2,4-Triazole-3-thione,2,4-dihydro-5-methyl-4-phenyl-3H-1

6232-82-2
13 suppliers
$219.00/500mg

Yield:6232-82-2 79%

Reaction Conditions:

with potassium hydroxide in water; for 3 h;Reflux;

Steps:

2.4.1 3-Mercapto-4-phenyl-5-methyl-1,2,4-triazole, 1

To a solution of acethydrazide (814mg, 10 mmole, 90% purity) in abs. ethanol (10mL), phenyl isothiocyanate (1.35g, 10 mmole) was added. The mixture was heated at reflux temperature for 1h, it was allowed to cool at room temperature, and then it was refrigerated for 3h. The crystalline material was filtered, sequentially washed with cold isopropanol (2×5mL) and hexanes (1×10mL), and air-dried. The resulting 2-acetyl-N-phenylhydrazine-1-carbothioamide (1.96g, 9.38 mmole) was added to a solution of KOH (741mg, 11.25 mmole, 85% purity) in water (30mL), and the mixture was heated at reflux temperature for 3h. The cold reaction mixture was filtered, and then the filtrate was treated dropwise under efficient stirring with 10% HCl until pH2. The solid material was filtered, washed thoroughly with water, air-dried and recrystallized to give colorless crystals (1.415g, 79%), mp 214-215°C (ethanol). IR spectrum (KBr pellet), ν_max: 3099s, 3051s, 2916s, 2906s, 2758m, 2729s, 1582m, 1501vs. ¹H NMR, (400.13MHz, δ (ppm), DMSO-d₆): 13.65 (s, 1H, NH), 7.59-7.42 (m, 5H, aromatic protons), 2.09 (s, 3H, CH₃). ¹³C NMR, (100.6MHz, δ (ppm), DMSO-d₆): 167.4 (C=S), 149.1 (C-CH₃), 133.8 (C-N), 129.3, 128.1 (aromatic carbon atoms), 11.7 (CH₃). Anal. Calcd. for C₉H₉N₃S (M=191.25g/mol), %: C, 56.52; H, 4.74; N, 21.97; S, 16.77. Found: C, 56.34; H, 4.52; N, 21.85; S, 16.87.

References:

Turcan-Trofin, Georgiana-Oana;Zaltariov, Mirela-Fernanda;Roman, Gheorghe;Shova, Sergiu;Vornicu, Nicoleta;Balan-Porcarasu, Mihaela;Isac, Dragos Lucian;Neamtu, Andrei;Cazacu, Maria [Journal of Molecular Liquids,2019,vol. 294,art. no. 111560]