Category: Triazoles

Reference of 1533519-85-5,Some common heterocyclic compound, 1533519-85-5, name is Methyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate, molecular formula is C18H17N3O2S, 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.

In a 5L three-necked flask, add 160.0g of Intermediate 4 and 1.28L of tetrahydrofuran, start stirring, and raise the temperature to 3542.0.Stir until dissolved; lower the temperature to 2732, add 148.0g NBS, and react for 3.04.0h;Reduce the temperature to 5, add 800ml of toluene and 800ml of purified water, stir and separate the liquid, and use 800ml of 3% sodium bisulfite solution for the organic phase,Wash with 800ml of 5% sodium bicarbonate solution, let stand for liquid separation, collect the organic phase, add 580ml of 1mol/L sodium hydroxide to the organic phase, react for 2h,Separate the liquid, collect the aqueous phase, concentrate, cool the crystal, filter, and wash with water to obtain a wet product; add 720ml of purified water to the wet product,Heat to 35, stir to dissolve, add 1.6L of ethyl acetate, adjust the system pH=24 with 24% hydrobromic acid, stir for 30min,Separate the liquid, wash the organic phase once with 320ml of purified water, concentrate the organic phase until the solid precipitates,Keep warm at 3842, continue to stir and crystallize for 34h, then slowly reduce the temperature to 510, stir for 2h,Filtration, washing, and vacuum drying under reduced pressure to obtain 123.0 g of crude Recinald. The purity is 95.12%,

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

Reference:
Patent; Beijing Xinkaiyuan Pharmaceutical Technology Co., Ltd. Hainan Fen Corporation; Xia Zhongning; Wu Jin; Zhang Lijie; (8 pag.)CN111153862; (2020); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 41253-21-8,Some common heterocyclic compound, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, 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.

1-2. Preparation of 1-(3-chloropropyl)-1,2,4-triazole (compound of formula 3) A 1,2,4-triazole sodium salt (5g, 54.91mmol) was dissolved in dimethylformamide (50mL) and the solution was cooled to 0. Then, sodium hydride (60%, 2.86g, 71.38mmol) was added thereto, followed by stirring for 30 minutes. 1-bromo-3-chloropropane (6.5mL, 65.89mmol) was added thereto, followed by stirring at room temperature for 12 hours, and the reaction was terminated with the addition of an ammonium chloride saturated solution. After extraction with ethyl acetate and water, the organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography to afford the title compound (2.77g, 35%).1H NMR (CDCl3, 400MHz): delta 8.08 (s, 1H), 7.94 (s, 1H), 4.36 (t, J =6.4Hz, 2H), 3.45 (t, J =6Hz, 2H), 2.35-2.30 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Sodium 1,2,4-triazol-1-ide, its application will become more common.

Reference:
Patent; DONG-A PHARM.CO., LTD.; KIM, Soon-Hoe; IM, Weon-Bin; CHOI, Sung-Hak; CHOI, Sun-Ho; SOHN, Ju-Hee; SUNG, Hyun-Jung; KIM, Mi-Yeon; CHO, Kang-Hun; SOHN, Tae-Kyoung; WO2011/132901; (2011); A2;,
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. 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione, A new synthetic method of this compound is introduced below., Safety of 4-Phenyl-1,2,4-triazolidine-3,5-dione

General procedure: Dimedone (0.14 g, 1 mmol), benzaldehyde (0.1 g, 1 mmol), and 4-phenylurazole (0.177 g, 1 mmol) were mixed with PEG-SO3H (0.6 g, 0.1 mmol) and the obtained mixture was stirred magnetically at 80 C for 40 min. After the completion of the reaction warm water (20 mL) was added and the mixture stirred for about 5 min. The insoluble crude product was filtered and recrystallized from EtOH/H2O 4:1 and the pure product was obtained (0.352 g, 91%). In order to recover the catalyst, the filtrate was dried under reduced pressure and recovered catalyst was washed with diethyl ether and reused after drying under reduced pressure. The equivalent procedure was used for the synthesis of triazolo[1,2-a]indazole-tetraones.

The synthetic route of 15988-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hasaninejad, Alireza; Zare, Abdolkarim; Shekouhy, Mohsen; Tetrahedron; vol. 67; 2; (2011); p. 390 – 400;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 129027-65-2, 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. 129027-65-2, name is 1-(tert-Butyl)-1H-1,2,3-triazole-4-carbaldehyde, This compound has unique chemical properties. The synthetic route is as follows.

To a 250-mL round bottom flask was added a solution of 1-tert-butyl-1H-1,2,3-triazole-4-carbaldehyde (2.47 g, 16.1 mmol, 2.2 eq) in dichloroethane, followed by addition of propargyl amine (361 mg, 72 mmol, 1.0 eq). To this mixture sodium triacetoxyborohydride (3.8 g, 17.9 mmol, 2.5 eq) was added in one portion with vigorous stirring. The reaction mixture was stirred at room temperature for 40 h. 1N H2SO4 (86 mL) was added to the reaction, and the mixture was stirred for 15 min. The pH was adjusted to >10 by addition of potassium carbonate. The reaction mixture was diluted with water (100 mL) and extracted with dichloromethane (3¡Á300 mL). The organic layers were combined, dried over anhydrous MgSO4, and filtered. Solvent was removed and the residue was purified on column to afford the product as a white powder. 1H NMR complies with the reported value.

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

Reference:
Patent; UNIVERSITY OF PITTSBURGH – OF THE COMMONWEALTH SYSTEM OF HIGHER EDUCACATION; Zeng, Dexing; (26 pag.)US2017/297008; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 41253-21-8, 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 41253-21-8 as follows.

Intermediate 38: 4-Cyclohexyl-4- [ (1, 2, 4-triazol-1-yl) methyl] piperidine Step A: 1-BOC-4-Cyclohexyl-4- [ (1, 2, 4-triazol-1-yl) methyl] piperidine To a solution of 1-BOC-4-cyclohexyl-4- [ (methanesulfonyloxy) methyl] piperidine (375 mg, 1 mmol) in DMF (10 mL) was added Na-1, 2,4-triazole (273 mg, 3 mmol), and the solution was stirred at 90-100C for 12 h. After DMF was distilled off in vacuo, the reaction mixture was quenched wirh a saturated aqueous NH4C1 solution, and the organic material was extracted with EtOAc. The extracts were dried over MgS04, filtered, and concentrated in vacuo. The residue was purified by column chromatography (eluent : acetone/DCM = 3/1) to give the title compound (313 mg, 90%). MS [M+H] = 349 (M+1)

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; LG LIFE SCIENCES LTD.; YAMANOUCHI PHARMACEUTICAL CO., LTD.; WO2005/47253; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1157938-97-0, name is 1-(2,5-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone, 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 1157938-97-0, name: 1-(2,5-Difluorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone

a) Preparation of a Stock-solution of lithium-diisopropylamide (LDA) in tetrahydrofuran (THF): Diisopropylamine (716 mg, 7,1 mmol, 1.05 eq) was dissolved in anhydrous THF (21.3 mL) and the resulting solution was cooled to -78 C under a nitrogen atmosphere. Subsequently, -BuLi (2,7 M solution in w-heptane, 2.5 mL, 6.7 mmol, 1,0 eq) was added in a drop wise fashion over 15 minutes and the reaction mixture was stirred at -78 C for an additional 15 minutes. Then the solution was warmed to 0 C and stirred for 30 minutes after which the stock solution was cooled to -78 C again, b) Coupling reaction: The thus obtained LDA-solution (3,66 mL, 0.98 mmol, 1.1 eq) was transferred to a Schlenk vessel and ethylpropionate (100 mg, 0.98 mmol, 1.1 eq.) was added in a drop wise fashion at -78 C under a nitrogen atmosphere. The resulting mixture was stirred at -78 C for 30 minutes and then l-(2,5-difluorophenyl)-2-(lH-l,2,4-triazol-l-yl)ethanone (200 mg, 0.90 mmol, 1.0 eq.) in THF (3.66 mL) was added in a drop wise fashion over 15 minutes. The reaction mixture was stirred for 2 hours at -78 C and then quenched with acetic acid and warmed to room temperature. The mixture was diluted with aqueous saturated NH4C1 and ethylacetate. The aqueous layer was extracted with ethylacetate (2x) and the combined organic layers were washed with brine, dried (Na2S04), filtered and concentrated in vacuo to give a yellow oil containing the racemic ester I with a diastereomeric excess of 29% in favour of the desired RR/SS diastereomer. Further purification by column chromatography (-heptane/EtOAc/MeOH 60/40/5 v/v/v) provided the RR/SS diastereomer (light yellow solid) as well as the RS/SR diastereomer (off-white solid) in a combined overall yield of 179 mg (0.55 mmol, 61%).

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; BASILEA PHARMACEUTICA AG; VAN SUMMEREN, Ruben; VAESSEN, Harrie; MINK, Daniel; WASER, Mario; WO2014/23623; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. category: Triazoles

To a mixture of l-fluoro-2-nitrobenzene (1 mL, 12.8 mmol, 1.0 equiv.) and 3-methyl- lH-l,2,4-triazole (1.27 g, 15.3 mmol, 1.2 equiv.) in acetonitrile (20 mL) was added potassium carbonate (5.29 g, 38.3 mmol, 3.0 equiv.) and the mixture was stirred at 60C for 12 hours. The mixture was cooled to 20C, diluted with ethyl acetate (20 mL) and filtered. The filtrate was concentrated under reduced pressure to give a residue which was purified by silica gel chromatography (petroleum ether: ethyl acetate 2: 1 to 1 : 1) to give the desired product as a light yellow solid (1.20 g, 46%); 1H NMR (DMSO-d6, 400 MHz) delta 8.96 (s, 1H), 8.12 (d, 71H), 7.90 – 7.88 (m, 1H), 7.86 – 7.84 (m, 1H), 7.60 (t, 7 = 8.0 Hz, 1H), 2.31 (s, 3H).

The synthetic route of 7170-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIRE HUMAN GENETIC THERAPIES, INC.; MILLER, Thomas; PAPAIOANNOU, Nikolaos; (243 pag.)WO2018/144620; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 88671-89-0, 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 88671-89-0 as follows.

EXAMPLE B-2 (Procedure B) 2-(4-chlorophenyl)-2-[(1,2,4-triazol-1-yl)methyl]hexanamide To a 500 mL flask was charged 75.0 g (0.24 mole) of alpha-n-butyl-alpha(4-chlorophenyl)-1H-1,2,4-triazole-1-propanenitrile followed by 300 mL of 95% sulfuric acid. The mixture was stirred at 90 C. for 7 days after which the mixture was cooled to room temperature, diluted with ice and neutralized with ammonium hydroxide until basic (pH 8). The product was extracted with ethylene dichloride then washed with water and dried over magnesium sulfate. The solvent was concentrated and gave 45 g (56.5% yield) of a solid melting point 197-199 C.

According to the analysis of related databases, 88671-89-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Rohm and Haas Company; US5358939; (1994); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 217448-86-7, 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. 217448-86-7, name is Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Example 8; Synthesis of compound (I): 1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxyamide (Rufinamide) Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate (II) (10.6 g, 41.9 mmoles), prepared as reported in Example 7, is dissolved in methanol (10 ml) and treated at room temperature under stirring with a 30% ammonia aqueous solution (40 ml), then the reaction mixture is refluxed and kept under stirring for 3 hours. The mixture is cooled to 20C, then diluted with water, filtered, and the resulting white solid is washed with water and dried in a static dryer at 50C. Rufinamide (8.7 g) is obtained as a crystalline white solid in 87% yield. 1H NMR (400 MHz, DMSO-d6), delta ppm: 8.56 (s, 1 H), 7.87 (bs, 1H), 7.60-7.43 (m, 2H), 7.20 (m, 2H), 5.72 (s, 2H).

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

Reference:
Patent; Dipharma Francis S.r.l.; EP2230234; (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. 288-36-8, name is 1H-1,2,3-Triazole, A new synthetic method of this compound is introduced below., Product Details of 288-36-8

2-iodobenzoic acid (1 g, 4.03 mmol), 2H-l,2,3-triazole (0.334 g, 4.84 mmol), copper(I) iodide (0.768 g, 4.03 mmol), cesium carbonate (2.63 g, 8.06 mmol) were reacted in DMF at 120 C under microwave irradiation for 20 minutes. Then the reaction was monitored confirming the presence of the required product. Large amount of starting material resulted left. The reaction was further irradiated for 20 minutes at 120 C. Solvent was then removed under vacuum, poured into water (100 ml) and neutralised with 37% HC1. Aqueous phase was extracted with Et20 (3×100 ml), and the collected organic phases were concentrated to give 1 g of crude material. This was purified with Biotage SP1 (over a 340g C18 column) eluting with a gradient of ACN and water (modified with 0.5% HCOOH). Fractions were collected and concentrated under vacuum to give the title compound D43 as colourless solid (140 mg). UPLC (GEN QC Basic): rt = 0.29 minutes, peak observed: 188 (M-l) C9H7N302 requires: 189. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 6.47 (br. s., 1 H) 7.47 – 7.59 (m, 1 H) 7.66 (t, 1 H) 7.75 – 7.87 (m, 3 H) 7.91 (d, 1 H)

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DI FABIO, Romano; WO2012/89606; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics