Triazoles

Some common heterocyclic compound, 28938-17-2, name is 4,5-Dibromo-2-methyl-2H-1,2,3-triazole, molecular formula is C3H3Br2N3, 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. category: Triazoles

4-bromo-2-methyl-2H-l,2,3-triazole. n-Butyllithium (8.3 mL) was added dropwise to a solution of 4,5-dibromo-2-methyl-2H-l,2,3-triazole (2.0 g, 8.37 mmol) in tetrahydrofuran (50 mL) under -78C, Once addition was completed, the mixture was stirred for another 30 minutes at -78C. The reaction was quenched with water, extracted with ethyl acetate (50 mL x 3), washed by brine (30 mL x 3). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated in vacuo to afford 4-bromo-2-methyl-2H- 1,2,3- triazole.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28938-17-2, its application will become more common.

Reference:
Patent; CONSTELLATION PHARMACEUTICALS, INC.; ALBRECHT, Brian, K.; GEHLING, Victor, S.; HEWITT, Michael, C.; TAYLOR, Alexander, M.; HARMANGE, Jean-Christophe; WO2012/151512; (2012); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 956317-36-5, 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. 956317-36-5 name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, 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.

To a solution of compound 6 (2.40 g, 11.76 mmol), compound 5 (2.86 g, 14.11 mmol), 1-hydroxy-1H-benzotriazole (1.90 g, 14.11 mmol), and dry triethylamine (3.56 g, 35.28 mmol) in 18 mL of dry DMF was added EDC hydrochloride (2.70 g, 14.11 mmol), and the reaction was stirred 2 h at room temperature. The reaction was partitioned between EtOAc and saturated aqueous NaHCO3, the layers were separated and the organic was added to aqueous citric acid stirring for 1 h. Water was added and the mixture was partitioned. Combined the water layers and added saturated aqueous Na2CO3 to regulate pH > 9, then extracted with three portions of EtOAc. The organic layers were combined, dried over MgSO4 and concentrated by rotary evaporation to provide compound 7 as a white power 4.30 g in 93% yield. Mp: 108-109 C, [alpha]D25 -58.4 (c 1.01, MeOH). 1H NMR (600 MHz, DMSO-d6): delta 8.00-7.76 (m, 3H), 7.37-7.17 (m, 7H), 4.40-4.09 (m, 1H), 3.63-3.48 (m, 2H), 3.44-3.02 (m, 3H), 2.82-2.75 (m, 1H), 2.63-2.47 (m, 1H), 2.63-2.14 (m, 5H), 2.02- 1.63 (m, 2H), 1.17-0.99 (m, 3H); MS (ESI) m/z: 390.30 [M+H]+. HR-MS(ESI): m/z [M+H] calcd. for C23H27N5O: 390.2288; found: 390.2281.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, and friends who are interested can also refer to it.

Reference:
Article; Chen, Yin; Zhou, Yan; Li, Jun-Hong; Sun, Jia-Quan; Zhang, Gui-Sen; Chinese Chemical Letters; vol. 26; 1; (2015); p. 103 – 107;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7411-23-6, These common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-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.

Step 1:To a suspension of NaH (60% in mineral oil, 194.0 mg, 4.8 mmol) in THF (20 mL) at 000 is added a solution of triazole A6a (1 .0 g, 4.4 mmol, Matrix) in THF (20 mL). The reaction mixture is allowed to warm to RT and is stirred for 30 mm. It is then cooled again to 0C and allyl bromide A9a (762.9 iL, 8.8 mmol, Aldrich) is added. The reaction mixture is stirred overnight at RT and diluted with EtOAc (50 mL). The organic layer is washed with water (25 mL) and brine (25 mL), dried over Mg504, and filtered. The filtrate is concentrated to give A9b which is used as is in subsequent steps.

The synthetic route of 7411-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; FADER, Lee; BILODEAU, Francois; POIRIER, Maude; PARISIEN, Mathieu; KUHN, Cyrille; THIBEAULT, Carl; TRINH, Thao; WO2014/70978; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 61-82-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 61-82-5, name is 1H-1,2,4-Triazol-5-amine belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 3-amino-1,2,4-triazole or benzimidazole (1.0 mmol), benzaldehyde (1.0 mmol), dimedone (1.0 mmol), and acetonitrile (5 mL) was taken in a round bottom flask and added iodine (10 mol %) and stirred at 80 C for 10 min. After completion of the reaction, as monitored by TLC, the reaction mass was cooled to room temperature and the solid separated was filtered and washed with water and dried at reduced pressure.Data of representative examples

The synthetic route of 1H-1,2,4-Triazol-5-amine has been constantly updated, and we look forward to future research findings.

Reference:
Article; Puligoundla, Ravinder Goud; Karnakanti, Shuklachary; Bantu, Rajashaker; Nagaiah, Kommu; Kondra, Sudhakar Babu; Nagarapu, Lingaiah; Tetrahedron Letters; vol. 54; 20; (2013); p. 2480 – 2483;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine, 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 4923-01-7, Application In Synthesis of 5-Methyl-4H-1,2,4-triazol-3-amine

2-(2,3-Dihydrobenzofuran-5-yl)-N-(3-methyl-1H-1,2,4-triazol-5-yl)thiazole-4- To a mixture of 2-(2,3-dihydro-l-benzoruran-5~yl)-l,3-thiazole-4-carboxylic acid (126 mg, 0.51 mmol), lH-l ,2,4-triazol-5-amine (50 mg, 0.51 mmol) and 2-(lH-benzotriazole-l-yl)- 1 ,1 ,3,3-tetramethyluroniurn hexafluorophosphate (HBTU) (120 mg, 0.32 mmol) under stirring and heating at 1 10 C 2 ml of dry pyridine were added. The mixture was heated at 110 C for 5 h, pyridine was evaporated, and the residue was diluted with an aqueous Na2C03 solution. The resulting precipitate was filtered off, dissolved in hot NN-dimethylformamide, settled by addition of EtOAc and hexane, filtered off and dried. The product was obtained as a light yellow solid (82 mg, 0.25 mmol, 49 % yield). NMR (400 MHz, OMSO-d6, CC14) delta ppm 2.29 (3 H, bs, CH3), 3.30 (2 H, t, CH2CH20), 4.64 (2 H, t, OCH2), 6.80 (1 H, d, CH-arom.), 7.82 (1 H, d, CH-arom.), 8.00 (1 H, s, CH-arom.), 8.31 (1 H, bs, CH-thiazol), 1 1.20 (1 H, bs, NH), 12.95 (1 H, bs, NH). LC/MS [M+H]+: 328.0

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Methyl-4H-1,2,4-triazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; 4SC DISCOVERY GMBH; LEBAN, Johann; ZAJA, Mirko; WO2014/202638; (2014); 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. 584-13-4, name is 4H-1,2,4-Triazol-4-amine, A new synthetic method of this compound is introduced below., COA of Formula: C2H4N4

General procedure: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.2mg, 0.05mmol), iodoalkene (1-4) or iodoarene (5-19) (1mmol) were dissolved in DMF (10mL) under argon in a three-necked flask equipped with a reflux condenser and a balloon on the top. Aminotriazole nucleophile (a, b or c) (1.2mmol) and triethylamine (0.5mL) were added. The atmosphere was changed to carbon monoxide. (Caution: High pressure carbon monoxide should only be used with adequate ventilation (hood) using CO sensors as well.) The reaction was conducted for the given reaction time upon stirring at 70C. The mixture was then concentrated and evaporated to dryness. Toluene (15mL) was added to the residue, the precipitate (product) was filtered, washed with water on the filter and dried. The off-white powder-like material was dissolved in methanol, the palladium-black was filtered off and methanol was evaporated.

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:
Article; Gergely, Mate; Boros, Borbala; Kollar, Laszlo; Tetrahedron; vol. 73; 48; (2017); p. 6736 – 6741;,
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. 13423-60-4, name is 1-Phenyl-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., Safety of 1-Phenyl-1H-1,2,4-triazole

A mixture of 1-phenyl-H-1,2,4-triazole 24 (364.3 mg, 2.51 mmol) and 2-fluoroethyl triflate (492.7 mg, 2.5 mmol) in toluene (2.5 ml) was heated at 130 C for 48 h. The solvent was evaporated and ther esidue titruated with Et2O (10 ml) to give the product as a white solid (803 mg, 94%).

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:
Article; Paul, Susann; Schweizer, W. Bernd; Rugg, Graham; Senn, Hans Martin; Gilmour, Ryan; Tetrahedron; vol. 69; 27-28; (2013); p. 5647 – 5659;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 16681-65-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 1-methyl-1 H-1 ,2,3-triazole (Preparation 32, 0.1 g, 1.2 mmol) in tetrahydrofuran (THF, 10 ml) at -780C was added dropwise 1.6 M n-butyl lithium (0.9 ml, 1.4 mmol), maintaining the temperature below -6O0C. The reaction was stirred at – 780C for 30 minutes, then dimethylformamide (0.14 ml, 1.8 mmol) was added. The reaction was warmed to room temperature and stirred for 1 hour. The reaction was quenched with water and extracted with ethyl acetate (3 x 10 ml). The combined organic extracts were washed with water (3 x 10 ml), dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography, eluting with 95:5 to 100:0 dichloromethane:methanol, to afford the title compound as a yellow oil (0.04 g, 30% yield).1HNMR (CDCI3): 4.10 (s, 3H)1 7.88 (s, 1 H), 9.55 (s, 1 H)

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-Methyl-1H-1,2,3-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; WO2008/135826; (2008); A2;,
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. 61-82-5, name is 1H-1,2,4-Triazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1H-1,2,4-Triazol-5-amine

General procedure: 20 mg of gamma-Fe2O3Ph-PMO-NaHSO4 was added to a roundbottomflask containing an aromatic aldehyde (1 mmol), 3-amino-1,2,4-triazole 2 (1.0 mmol), b-diketones (dimedone 3, 1,3-cyclohexadione 4 or ethyl acetoacetate 5) (1.0 mmol) and stirredunder solvent-free conditions at 100 C in certain times. Meanwhile,the progress of the reactionwas indicated by TLC (n-hexane:ethyl acetate; 7:3). With completing the reaction, 3ml ethanol waspoured and the magnetic nanocomposite was separated in thepresence of a magnetic stirring bar; the reaction mixture becameclear. The crude product was recrystallized from ethanol to give thepure product. The pure products were characterized by conventionalspectroscopic methods. Physical and spectral data for theselected compounds are represented below.

According to the analysis of related databases, 61-82-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Haghighat, Mahdieh; Shirini, Farhad; Golshekan, Mostafa; Journal of Molecular Structure; vol. 1171; (2018); p. 168 – 178;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-65-5, name is 1-Methyl-1H-1,2,3-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 16681-65-5, category: Triazoles

Step B: To a solution of l-methyl-lH-l,2,3-triazole (860 mg, 10.4 mmol) in THF (10 mL) at -78 C, was added dropwise n-BuLi (5.0 mL, 12.4 mmol, 2.5 M). The mixture was stirred at -78 C for 2 hours before addition of BusSnCl (3.7 g, 11.4 mmol). The mixture was stirred at -78 C for 1 hour and then room temperature for 1 hour. The mixture was concentrated under vacuum and hexane was added. The insoluble material was filtered and the filtrate was concentrated under vacuum to afford l-methyl-5-(tributylstannyl)-lH-l,2,3-triazole (3.1 g, 80 %) as yellow oil which was used directly in the next step.

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:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; YUK, Inn H.; PURKEY, Hans; O’BRIEN, Thomas; WO2015/142903; (2015); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics