Measurement and Correlation of Solubility of Methyl 1,2,4-Triazole-3-carboxylate in 14 Pure Solvents from 278.15 to 318.15 K

Abstract

The solubility of methyl 1,2,4-triazole-3-carboxylate in 14 solvents (methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, isobutyl alcohol, acetonitrile, acetone, 2-pentanone, 3-pentanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, tetrahydrofuran) in the range from 278.15 to 318.15 K and at atmospheric pressure was measured in this study. The solubility of methyl 1,2,4-triazole-3-carboxylate in all solvents increases with the increasing temperature. The solubility of methyl 1,2,4-triazole-3-carboxylate in the solvents except for methanol and cyclohexanone does not show much difference, and is significantly smaller than that in methanol and cyclohexanone. The solubility of methyl 1,2,4-triazole-3-carboxylate is not strictly related to polarity of the solvents as it is to the existence of other factors. The solubility of methyl 1,2,4-triazole-3-carboxylate was correlated by the λh equation, modified Apelblat model, and Yaws model. The Yaws model is the best one among the three models with average relative deviation (ARD) and average root-mean-square deviation (104(RMSD)) of 1.18% and 0.364. The work in this study provides important solubility data for purification and synthesis of methyl 1,2,4-triazole-3-carboxylate.

Measurement of Solubility and Molecular Simulation of Dissolution Behavior of Isonicotinamide in 15 Pure Solvents

“…A semiempirical model describing the linear relationship between solubility and temperature was proposed by Yaws in 1999. Solubility data and temperatures were commonly correlated using the Yaws model. − The three parameters of this model are A Yaws , B Yaws , and C Yaws , and the expression can be described as eq . …”

Solubility Determination, Modeling, and Thermodynamic Analysis of 3-Aminophenol in Ten Monosolvents and Three Binary Mixed Solvents

“…The Yaws model , can be expressed as follows ln nobreak0em0.25em⁡ x 1 = D + E T + F T 2 where x 1 is the mole fraction of 3-aminophenol, T is the absolute thermodynamic temperature, and D , E , and F are model parameters.…”

Comprehensive Review on the Synthetic Strategies toward Anti-SARS-CoV-2 Drug Ensitrelvir

“…As shown in Figure 3A, commercially available chloroacetonitrile (35 USD/kg) was first reacted with methanol to obtain acetimidate under basic condition to form methyl 2chloroacetimidate 5, 19 and then N-methyl-N-formylhydrazine was used for the cyclization reaction to obtain the 1,2,4-triazole scaffold. 20 Finally, chlorination was performed with POCl 3 with a 54.0% yield on a 39 g scale from the starting material. 21 The key methyl 2-chloroacetimidate 5 was also obtained under acidic conditions.…”

“…21 The key methyl 2-chloroacetimidate 5 was also obtained under acidic conditions. 20 A one-pot procedure was developed starting from N-methyl-N-formylhydrazine and chloroacetonitrile using similar reagents with a yield of 82.0% on a 30 g scale. Although toxic chloroacetonitrile was unavoidable, as we know, the synthetic strategy was used as a recommended protocol for the pilot scale.…”

“…Thereafter, cyclization was performed with methyl hydrate using sulfuric acid as catalyst with up to 90.6% yield at the 120 g scale. 20 The alternative strategy for the preparation of 2-chloro-N-formylacetamide 6, oxidation of 2chloro-N-(hydroxymethyl)acetamide, was reported using manganese dioxide (MnO 2 ) in a 70.0% yield. 22 However, the advantages of the price of starting material 2-chloro-N-(hydroxymethyl)acetamide and the yield of the first step with unmanageable waste (MnO 2 ) were not remarkable.…”