Extracurricular laboratory: Synthetic route of 1H-1,2,3-Triazole

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 288-36-8, and friends who are interested can also refer to it.

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-bromo-3-thiophene carboxylic acid (1.50 g, 7.24 mmol), 1H-1 ,2,3- triazole (0.600 g, 8.69 mmol), potassium carbonate (2.00 g, 14.5 mmol), and copper iodide (0.138 g, 0.724 mmol) in DMF (36.2 mL) was purged subsurface with nitrogen and heated to 75 C for 4 nights. The reaction was diluted with water, washed with ether, and acidified with cone. HC1. The acidic aqueous solution was extracted 3x with ethyl acetate and the combined organic fractions were washed with brine, dried over magnesium sulfate, filtered, and concentrated. The crude material was purified by silica gel gradient chromatography [0-70% (1% acetic acid in ethyl acetate) in hexanes], providing the title compound as an off-white solid. LRMS m/z (M+H) 196.2 found, 196.1 required.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 288-36-8, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; SKUDLAREK, Jason, W.; WO2015/95442; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Introduction of a new synthetic route about 3,5-Dimethyl-4H-1,2,4-triazole

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.

7343-34-2, 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. 7343-34-2, name is 3,5-Dimethyl-4H-1,2,4-triazole, A new synthetic method of this compound is introduced below.

4-chloro-6-(3,5-dimethyl-lH-l,2,4-triazol-l-yl)-2-methylpyrimidine (1-2) To a slurry of 4,6-dichloro-2-methylpyrimidine (1-1) (5.00 g, 30.7 mmol) and cesium carbonate (15.0 g, 46 mmol) in DMF (250 mL) at 0 ¡ãC was added a solution of 3,5-dimethyl-lH- 1,2,4- triazole (2.98 g, 30.7 mmol) in DMF (50 mL) via a dropping funnel over 1 h. The reaction was then warmed to room temperature and stirred for 1 h. The reaction was quenched by addition of water (500 mL) and extracted with ethyl acetate (3 x 400 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated. The crude product was purified by silica gel column chromatography (0-30percent EtOAc/hexanes) to afford 4-chloro-6-(3,5-dimethyl-lH- l,2,4-triazol-l-yl)-2-methylpyrimidine (1-2) as a white solid. XH NMR (400 MHz, CDC13) delta 7.75 (s, 1H), 2.91 (s, 3H), 2.72 (s, 3H), 2.41 (s, 3H); MS mlz = 224 (M+H).

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; MERCK SHARP & DOHME CORP.; BESHORE, Douglas, C.; JOHNSON, Adam, W.; KUDUK, Scott, D.; REGER, Thomas, S.; WO2014/78217; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Continuously updated synthesis method about 16681-65-5

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1-Methyl-1H-1,2,3-triazole.

Adding some certain compound to certain chemical reactions, such as: 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, 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. 16681-65-5

A 2.5 M solution of n-butyllithium in hexanes (9.60 mL, 24.0 mmol) was added dropwise to a stirring solution of 1-methyl-1H-1,2,3-triazole (2.00 g, 24.0 mmol, prepared according to PCT Int. Appl., 2008098104) in dry THF (100 mL) at -50 C. The reaction became heterogeneous and yellow during addition. After 15 minutes, a solution of tert-butyl 3-formylazetidine-1-carboxylate (4.45 g, 24.0 mmol) in dry THF (10 mL) was added dropwise by syringe. The reaction mixture became homogeneous and was allowed to slowly warm to 0 C. Water (10 mL) and ethyl acetate (100) mL were added. The biphasic mixture was warmed to 23 C. The mixture was partitioned between half-saturated aqueous sodium chloride solution (100 mL) and ethyl acetate (300 mL). The layers were separated. The organic layer was dried with sodium sulfate and the dried solution was filtered. Celite (14 g) was added to the filtrate and the solvents were removed by rotary evaporation to provide a free-flowing powder. The powder was loaded onto a silica gel column. Elution with ethyl acetate initially, grading to 5% methanol-ethyl acetate provided the title compound as a white foam.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1-Methyl-1H-1,2,3-triazole.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Brief introduction of 61-82-5

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1H-1,2,4-Triazol-5-amine.

Adding some certain compound to certain chemical reactions, such as: 61-82-5, name is 1H-1,2,4-Triazol-5-amine, 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 61-82-5. 61-82-5

A mixture of aldehyde (1 mmol), dimedone (1 mmol), 3-amino-1,2,4-triazole (1 mmol), and [C4(H-DABCO)2][HSO4]4 (16 mg) washeated in an oil bath (90 C) under solvent-free conditions. Aftercompletion of the reaction, as identified by TLC, using n-hexane:EtOAc (7:3) as the eluent, 10 mL of water was added and stirredfor 10 min. The catalyst was dissolved in water and the solid wasfiltered off and washed with warm EtOH, to obtain the pure targetmolecule.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 1H-1,2,4-Triazol-5-amine.

Reference:
Article; Safari, Niloufar; Shirini, Farhad; Tajik, Hassan; Journal of Molecular Structure; vol. 1201; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Share a compound : 1H-1,2,3-Triazole

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.

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. 288-36-8, name is 1H-1,2,3-Triazole, A new synthetic method of this compound is introduced below., 288-36-8

EXAMPLE B2-(2H-l,2.3-triazol-2-v0benzoic acid (B- 1)A solution of 2-iodobenzoic acid (3.0 g, 12.09 mmol) in DMF was treated with (1.5 g, 21.7 mmol) 1,2,3-triazole, 7.08 g (21.7 mmol) CsCO3, 1 14 mg (0.60 mmol) CuI and 310 mg (2.17 mmol) trans-N,N’-dimethylcyclohexane-l,2-diamine. The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to rt, diluted with EtOAc, and filtered through Celite. The residue was purified by gradient elution on SiO2 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting desired 2-(2H-l,2,3-triazol-2-yl)benzoyl acid, B-I . Data for IM : 1HNMR (500 MHz, DMSO-(I6) delta 13.05 (br s , IH), 8.12 (s, 2H), 7.81-7.52 (m, 4H) ppm. The undesired 2-(lH-l,2,3-triazol-2-yl)benzoic acid (B-2) eluted second.

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; MERCK & CO., INC.; WO2008/143856; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A new synthetic route of 7170-01-6

The chemical industry reduces the impact on the environment during synthesis 3-Methyl-1H-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

7170-01-6, The chemical industry reduces the impact on the environment during synthesis 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life.

Example 50. Synthesis of compound (R)-6-(4-chlorophenyl)-l,4-dimethyl-8-(5- methyl-lH-l,2,4-triazol-l-yl)-5,6- dihydro-4H-benzo[b][l,2,4]triazolo[4,3-d][l,4]diazepine (Compound 65) and (R)-6-(4-chlorophenyl)-l,4 -dimethyl-8-(3-methyl-lH-l,2,4-triazol-l- yl)-5,6-dihydro-4H-benzo[b][l,2,4]triazolo[4,3-d][l,4]diazepine (Compound 66). A mixture of (R)-8-bromo-6-(4-chlorophenyl)-l,4-dimethyl-5,6-dihydro-4H-benzo[b][l,2,4]triazolo [4,3- d][l,4]diazepine (60 mg, 0.15 mmol), 3-methyl-lH-l,2,4-triazole (14 mg, 0.16 mmol), copper (I) iodide (6 mg,0.03 mmol), 1,10-phenanthroline (11 mg, 0.06 mmol) and cesium carbonate (98 mg, 0.3 mmol) in dimethyl sulfoxide (3 mL) was heated at 130C for 30 minutes under microwave (pressure: 1.0 bar, equipment power : 150W). The reaction mixture was diluted with ethyl acetate (20 mL) and washed with brine (10 mL x 3). The organic phase was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated to give a crude product which was purified by column chromatography (silica gel, dichloromethane/methanol = 20:1) to afford (R)-6-(4-chlorophenyl)- 1 ,4-dimethyl-8-(5-methyl- 1H- 1 ,2,4-triazol- l-yl)-5,6-dihydro-4H- benzo [b][l,2,4]triazolo[4,3-d][l,4]diazepine (15 mg, 25%) and (R)-6-(4-chlorophenyl)-l,4- dimethyl- 8-(3-methyl-lH-l,2,4-triazol-l-yl)-5,6-dihydro-4H-benzo[b][l,2,4]triazolo[4,3- d][l,4]diazepine (8 mg, 13%) as a light yellow solid.

The chemical industry reduces the impact on the environment during synthesis 3-Methyl-1H-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

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

Analyzing the synthesis route of Sodium 1,2,4-triazol-1-ide

According to the analysis of related databases, 41253-21-8, the application of this compound in the production field has become more and more popular.

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 41253-21-8 as follows. 41253-21-8

e) Preparation of 2,2′-[5-(1H-1,2,4-triazole-1-yl-methyl)-1,3-phenylene]di(2-methyl propionitrile) (1)A mixture of 2,2′-(5-bromomethyl-1,3-phenylene)di(2-methylpropionitrile) (V) (4 gm, 0.013 moles) and 1,2,4-triazole sodium salt (2.40 gm, 0.026 moles) in N,N-dimethylformamide (28 ml) was heated under stirring at 45-50 C. for 4 hour. The reaction mixture was cooled, poured into the ice-water and extracted with ethyl acetate. The ethyl acetate layer was separated and concentrated to give a residue. This residue was diluted with water, acidified with concentrated hydrochloric acid (adjusted the pH tol-2). The reaction mixture was heated at 50 C. and subsequently filtered the hot solution. The mother liquor was treated with ammonia solution at 0-5 C. (adjusted the pH to 8-9) and extracted with ethyl acetate. The ethyl acetate layer was separated and concentrated to obtain a residue (3.0 g).f) Purification of Anastrozole by Column Chromatography and CrystallizationThis residue was purified through column chromatography by using silica gel column and ethylacetate-hexane (740 ml: 950 ml) as eluent. The solid (2.0 g) obtained was recrystallized using a mixture of acetone-water (12 ml: 20 ml) or ethylacetate-hexane mixture (9 ml to 18 ml) to obtain 2,2′-[5-(1H-1,2,4-triazole-1-ylmethyl)-1,3-phenylene]di(2-methyl propionitrile) (1). [Yield: 34.0%, purity, 99.9%].

According to the analysis of related databases, 41253-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Radhakrishnan, Tarur Venkatasubramanian; Baban, Bhise Nandu; Govind, Sathe Dhananjay; Janardan, Chaudhari Chhayendra; Ashokkumar, Joshi Mehul; US2008/207915; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Discovery of 1H-1,2,3-Triazole

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.

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., 288-36-8

To a mixture of the product from step 2 (7.9 g, 38 mmol), cesium carbonate (24.8 g,76 mmol) and CuT (2.88 g, 7.6 mmol) in DMF (200 mL) were added 2H-[1,2,3jtriazole (5.24 g,76 mmol) and N,N?-dimethyl-cyclohexane-1,2-diamine (0.9 g, 6.5 mmol) and the mixture was heated to 110C overnight. The cooled reaction mixture was adjusted to pH=12 with 1M sodium hydroxide aqueous solution and extracted with EtOAc (50 mL x 3). The aqueous layer wasadjusted to pH=4 with 1M HC1 aqueous solution and extracted with EtOAc (50 mLx4). The extracts was dried over Na2504, filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica (petroleum ether: EtOAc =10:1) to provide the title compound. LRTVIS m/z (M+H) 196.0 found, 196.0 required.

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; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (97 pag.)WO2016/100157; (2016); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Extended knowledge of 288-36-8

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 288-36-8.

288-36-8, Adding some certain compound to certain chemical reactions, such as: 288-36-8, name is 1H-1,2,3-Triazole, 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 288-36-8.

2-(2H-l,2,3-Triazol-2-vD-5-methylbenzoic acid (1-7)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 water with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid 1-5. followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. Data for K7: 1HNMR (500 MHz, DMSO-d6) d 12.98 (br s , IH), 8.04 (s, 2H), 7.72-7.45 (m, 3H), 2.41 (s, 3H) ppm.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 288-36-8.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; FRALEY, Mark, E.; SCHREIER, John, D.; WO2010/48017; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Share a compound : 7170-01-6

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7170-01-6.

7170-01-6, These common heterocyclic compound, 7170-01-6, name is 3-Methyl-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.

To a 50 mL dried two-neck flask were added 3-methyl-1H-1,2,4-triazole (650 mg, 7.8 mmol), 1-fluoro-4-nitrobenzene (1.0 g, 7.1 mmol) and potassium carbonate (2.0 g, 14 mmol), then DMF (10 mL) was added. The mixture was stirred at 80 C for 1 h under nitrogen protection. The mixture was cooled to rt and filtered. The filter cake was washed with DCM (20 mL), and the filtrate was concentrated in vacuo. To the residue was added water (20 mL). The mixture was stirred for 10 min and then a light yellow solid precipited out. The mixture was filtered by suction, and the filter cake was dried to give a light yellow solid (0.7 g, 48%). MS (ESI, pos.ion) m/z:205.1 (M+1)

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 7170-01-6.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; WANG, Xiaojun; ZHOU, Pingjian; YANG, Chuanwen; HUANG, Changwei; XIONG, Shaohui; ZHANG, Yingjun; ZHANG, Jiancun; (139 pag.)EP3342765; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics