Triazoles

Reference of 1455-77-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1455-77-2 name is 3,5-Diamino-1,2,4-triazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Added to three neck fever bottle 126mmol oleic acid, 60mmol3,5-diamino -1, 2, 4-three nitrogen […] 20.9g glycol solvent, under the protection of argon gas, heating 80 ¡ãC after melting, by adding 3mmol potassium hydroxide, wherein the oleic acid: 3,5-diamino -1, 2, 4-triazole: potassium hydroxide mole ratio is 2.1: 1 : 0.05, glycol as the above-mentioned reactant of the total weight of the 50percent. Continued heating to 150 ¡ãC, reaction 12h rear, with 1percent sodium carbonate water solution, in order to remove unreacted oleic acid and the solvent is ethylene glycol, yellow solid is obtained after drying a heterocycle-containing fatty acid amide-based intermediate A.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Diamino-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Patent; China Petroleum & Chemical Corporation; Yu, Jianye; Lu, Minhui; Yuan, Ping; Yuan, Yufeng; (9 pag.)CN105693640; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 1257633-67-2, These common heterocyclic compound, 1257633-67-2, name is 1-(tert-Butyl)-4-(diethoxymethyl)-1H-1,2,3-triazole, its 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.

Synthesis of 1-tert-butyl-1H-1,2,3-triazole-4-carbaldehyde To a 50-mL round bottom flask was added a solution of 1-tert-butyl-4-(diethoxymethyl)-1H-1,2,3-triazole (1.28 g, 5.63 mmol) in dichloromethane (6.0 mL), followed by addition of water (3.0 mL) and trifluoroacetic acid (1.0 mL). The reaction was stirred vigorously under nitrogen for 3 h until TLC analysis indicated the complete disappearance of the starting material (10% EtOAc in dichloromethane, starting material Rf 0.5, product Rf 0.6, KMnO4 stain). The reaction mixture was diluted with EtOAc (100 mL), washed with sat aq NaHCO3 (3*40 mL) and brine (40 mL). The combined organic phases were dried over anhydrous MgSO4, filtered, and concd in vacuo to provide 0.71 g of a light yellow oil (yield: 82%). The crude product was used without purification.

Statistics shows that 1-(tert-Butyl)-4-(diethoxymethyl)-1H-1,2,3-triazole is playing an increasingly important role. we look forward to future research findings about 1257633-67-2.

Reference:
Patent; Albert Einstein College of Medicine of Yeshiva Uni; Wu, Peng; Soriano del Amo, David; Wang, Wei; Marlow, Florence L.; US2013/295019; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 143426-50-0, name is 4-(1,2,4-Triazol-1-yl)benzyl Alcohol, belongs to triazoles compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 143426-50-0, COA of Formula: C9H9N3O

A mixture of 14 (100 mg, 0.34 mmol), [4-(1H-1,2,4-triazol-1-yl)phenyl]methanol16 (118 mg, 0.67 mmol)and (tributylphosphoranylidene)acetonitrile (163 mg, 0.68 mmol) in toluene (2 mL) wasstirred at 100 C for 1.5 h and allowed to cool to room temperature. Themixture was evaporated in vacuo and the crude mixture was purifiedusing amino-functionalized silica-gel column chromatography (CHCl3)and washed with diisopropyl ether to give N-ethyl-5-(2-methyl-8-{[4-(1H-1,2,4-triazol-1-yl)phenyl]methoxy}imidazo[1,2-a]pyridin-3-yl)pyridine-2-carboxamide (87 mg). Next, 4M HCl in EtOAc (0.20 mL,0.80 mmol) was added to a 2.2 mL EtOAc-EtOH (10:1) solution of thiscompound. After stirring at room temperature, the precipitate was filteredto give the product as a beige solid (87 mg, 49% yield [2 steps]).1H NMR (DMSO-d6) delta ppm 1.16 (3H, t, J=7.1 Hz), 2.50 (3H, s),3.33-3.43 (2H, m), 5.59 (2H, s), 7.39 (1H, dd, J=8.0, 6.9 Hz), 7.63(1H, d, J=8.2 Hz), 7.80-7.85 (2H, m), 7.94-7.99 (2H, m), 8.24-8.32(4H, m), 8.88 (1H, dd, J=2.0, 1.0 Hz), 8.96 (1H, t, J=6.1 Hz), 9.37(1H, s); MS (ESI) m/z [M+H]+ 454. HRMS (ESI) m/z calcd forC25H24N7O2 ([M+H]+): 454.1986. Found: 454.1989. Anal. calcd forC25H23N7O21.5HCl¡¤2.3H2O0.15EtOAc: C, 54.63; H, 5.43; N, 17.42;Cl, 9.45. Found: C, 54.87; H, 5.32; N, 17.72; Cl, 9.10.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(1,2,4-Triazol-1-yl)benzyl Alcohol, and friends who are interested can also refer to it.

Reference:
Article; Sekioka, Ryuichi; Honda, Shugo; Honjo, Eriko; Suzuki, Takayuki; Akashiba, Hiroki; Mitani, Yasuyuki; Yamasaki, Shingo; Bioorganic and Medicinal Chemistry; vol. 28; 1; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 288-36-8 as follows.

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1,2,3-triazole (2.1 g, 30.5 mmol), CsCO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dimethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-2, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. A solution of the acid (3.56 g, 17.52 mmol) in 150 mL of DCM was stirred and cooled to 00C. The solution was treated with oxalyl chloride (1.9 mL, 21.9 mmol) and DMF (68 muL, .878 mmol). The solution was slowly warmed to room temperature and stirred overnight. Solvent was concentrated and the resulting solid was azetroped with DCM and concentrated to provide A-4 as a yellow solid.

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; FLORES, Broc; SCHREIER, John, D.; WO2010/48016; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C2H3N3

To a solution of 5-fluoro-2-iodo- benzoic acid (3.86 g, 14.65 mmol), 2H-[1 ,2,3]triazole (2.5 g, 36.2 mmol),Cs2CO3 (8.62 g, 24.5 mmol), trans-N, N’-dimethyl-cyclohexane-1 ,2-diamine (0.4 ml_), Cul (244 mg) and DMF (13 ml_) were added to a microwave ready vessel and heated to 100 C for 10 min. The mixture was cooled, diluted with water, and extracted with EtOAc. The aqueous layer was acidified and extracted with EtOAc. The organic layer was dried over Na2SO and concentrated. The residue was purified by FCC (SiO2, gradient DCM to 10% MeOH/1 %HOAc/DCM) gave the product as a white powder, (2.14 g, 71 %). 1H NMR (400 MHz, CD3OD): 7.91 (s, 2H), 7.76 (dd, J = 8.9, 4.8 Hz, 1 H), 7.59 (dd, J = 8.5, 2.9 Hz, 1 H), 7.49 – 7.42 (m, 1 H).; Intermediate 53: 2-[1 ,2,3]Triazol-1 -yl-benzoic acid.The title compound was isolated from the synthesis of Intermediate 13. 1H NMR (400 MHz, CD3OD): 6.70 (d, J = 0.9 Hz, 1 H), 6.50 (dd, J = 7.7, 1 .5 Hz, 1 H), 6.30 (d, J = 1 .0 Hz, 1 H), 6.24.6.18 (m, 1 H), 6.17 -6.1 1 (m, 1 H), 6.01 (dd, J = 7.8, 1 .0 Hz, 1 H).

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 6523-49-5, These common heterocyclic compound, 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, its 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.

A solution of Intermediate 11 (96mg, 0.23mmol, leq), and 4-(7No.-l,2,4-triazol-l- yl)aniline (38mg, 0.24mmol, 1.05mmol) in acetic acid (2mL) was heated at reflux. After Ih the reaction was allowed to cool to room temperature, concentrated in vacuo and treated with a saturated aqueous solution OfK2CO3 until effervescence ceased. The resulting mixture was then concentrated in vacuo to dryness to yield a brown residue. The residue was purified using flash column chromatography, eluting initially with 200:8:1 and then 100:8:1 CH2Cl2 :EtOH:NH3. The title compound was isolated as an off-white solid (48mg, 40%). Rf = 0.39 (40:8:1 CH2Cl2:Et0H:NH3). 1H-NMR (DMSCwZ6) 2.11 (s, 6H), 2.17 (s, 3H), 2.43 (m, 2H), 2.68 (t, 2H), 4.08 (t, 2H), 7.23 (m, IH), 7.56 (m, IH), 7.75 (m, 3H), 7.93 (m, 2H), 8.08 (m, 2H), 8.50 (s, IH), 8.68 (s, IH), 9.14 (s, IH), 9.92 (br. s, IH). LC-MS rt 2.08 m/z 527 ES+

Statistics shows that 4-(1,2,4-Triazol-1-yl)aniline is playing an increasingly important role. we look forward to future research findings about 6523-49-5.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1533519-85-5, These common heterocyclic compound, 1533519-85-5, name is Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, its 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.

Example 11. Preparation of methyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate [076] To a flask added methyl 2-((4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate (4.0 g, 11.8 mmol), l,3-Dibromo-5,5-dimethylhydantoin (11.8 mmol) and ethyl acetate (100 mL) to form a mixture, the mixture was heated to reflux, after the reaction was complete, the mixture was cooled to room temperature, then worked up to obtain phenyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate as a yellow solid 4.9 g, yield 99%, LC-Ms: m/z (ESI): 418,420 (M+H)+, 1H NMR (400 MHz, CDC13): delta 8.57 (d, J=8.0 Hz, 1 H), 7.69 (m, 1 H), 7.61 (m, 1 H), 7.39 (s, 2 H), 7.26 (d, J=8.4 Hz, 1 H), 4.07 (dd, J=16.0, 25.6 Hz, 2 H), 3.75 (s, 3 H), 2.46 (m, 1 H), 1.20 (m, 2 H), 0.91 (m, 2 H).

The synthetic route of 1533519-85-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CHEN, Weiqiang; LUO, Jian; LIU, Lixue; FAN, Yuping; WO2014/198241; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, belongs to triazoles compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1455-77-2, Recommanded Product: 3,5-Diamino-1,2,4-triazole

To a solution of 54.2 g (0.786 mol) of sodium nitrite in63.3 mL water at -10 to -5 ¡ãC, we added a solution of 8 g(0.081 mol) of DAT in 169.5 mL 1.2 mol/L sulfuric acid for1.5 h, the reaction mixture was heated up to 60 ¡ãC and stirredfor another 1 h, then cooled the reaction mixture to roomtemperature. 26.9 mL 6 mol/L sulfuric acid and 4.7 g (0.048mol) aminosulfuric acid were added to reaction system andstirred for another 0.5 h, extracted with 90 ¡Á 5 mL of ether,dried with magnesium sulfate and the solvent was removedunder reduced pressure and 7.89 g yellow oil 3,5-dinitro-1,2,4-triazole (DNT) was obtained with a yield of 61.4 percent. 1H NMR(DMSO-d6, 500 MHz), d: 6.424 (s, 1H, NH); 13C NMR(DMSO-d6, 125 MHz), d: 162.56; IR (KBr, nmax, cm-1), 3224(-NH-), 1659, 1382 (-NO2); Anal. calcd for C2H3N5O5: C 13.57,N 39.55, H 1.71; found C 13.73, N 38.91, H 2.13; MS (m/z):159 [M+].

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Li, Ya-Nan; Liu, Ning; Su, Peng-Fei; Wang, Ying-Lei; Ge, Zhong-Xue; Li, Hui; Wang, Bo-Zhou; Asian Journal of Chemistry; vol. 26; 21; (2014); p. 7151 – 7156;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 288-88-0, name is 1H-1,2,4-Triazole, A new synthetic method of this compound is introduced below., name: 1H-1,2,4-Triazole

Example 2 Synthesis of 2-((1H-1,2,4-triazol-1-yl)methyl)-2-(2,4-difluorophenyl)-1,3-dioxolane-4-thiol Sodium triazole was prepared in-situ by azeotropically distilling a mixture of 1,2,4-triazole (0.5 mol), sodium hydroxide solution (50%, 35.2 mL), toluene, (250 mL) and dimethylsulfoxide (250 mL) to a Karl Fisher water content less than 0.4% (by a Karl Fisher titration). The solution was cooled to 25 C., then a anhydrous toluene solution of 2-(bromomethyl)-2-(2,4-difluorophenyl)-4-(ethylthio)-1,3-dioxolane (Chemical Structure 8, 1.8 mol) was added. The temperature was increased to 75 C. and held at that temperature to reaction completion (monitored by TLC). Then the reaction mixture was cooled to 35 C. and quenched with dilute sodium hydroxide aqueous solution slowly to keep the temperature below 45 C. After the resulting mixture was cooled to 25 to 35 C., water and toluene were added. After the phases were separated, the aqueous phase was washed with toluene 3 to 5 times. The combined organic phases were concentrated under a maximum temperature of 70 C. The ethyl group of the thioester (1 mol) was removed by treated the resulting residue with sodium methoxide (approximately 8 mol) in dimtheylformamide (300 mL). The reaction mixture was stirred under nitrogen over night at 120 C. After cooling to room temperature, the reaction was quenched by adding methyl iodide (5 mol) under constantly stirring. Then the mixture was poured into water (350 mL) and extracted with tert-butyl methyl ether (100 mL*3). The organic phase was washed with saturated sodium sulphate solution and condensed. The residue was dissolved in warm toluene and washed with dilute hydrochloric acid aqueous solution, up to two times. After filtration of the precipitate and crystallization from isopropanol/Isopropyl ether (8/2, v/v), the D form of Chemical Structure A where X is -SH was obtained in ~65% yield (Chemical Structure 9).

The synthetic route of 288-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wu, Nian; Keller, Brian Charles; US2010/143455; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., Recommanded Product: 7170-01-6

resultant compoundH N_is in turn reacted with three (3) equivalents of N in 4-Me-2-pentanol to produce

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; TRIPP, Jonathan Clive; FANFAIR, Dayne Dustan; SCHULTZ, Mitchell J.; MURUGESAN, Saravanababu; FOX, Richard J.; CHEN, Chung-Pin H.; IVY, Sabrina E.; PAYACK, Joseph Francis; DOUBLEDAY, Wendel W.; WO2012/106189; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics