Day: November 26, 2020

288-36-8, 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.

A mixture of 2,3-difluorobenzonitrile (4.0 g, 28.8 mmol), 2H-1 ,2,3-triazole (1 .9 g, 28.8 mmol) in DMF (85.0 ml_) and K2CO3 (7.9 g, 57.5 mmol) were heated to 125 oC for 1 .5 h. After cooling to rt, water was added and the mixture extracted with EtOAc (2 X). The combined organics were washed with brine and dried (Na2SO ). Purification via FCC (10-100% EtOAc in hexanes) gave two products. 3-Fluoro-2-(2H-1 ,2,3-triazol-2- yl)benzonitrile (1 .6 g, 29%), 1H NMR (CDCI3): 7.99 (s, J = 6.6 Hz, 2H), 7.67 – 7.63 (m, 1 H), 7.61 – 7.53 (m, 2H), 7.26 (s, 6 H) and 3-fluoro-2-(1 H-1 ,2,3-triazol- 1 -yl)benzonitrile (2.0 g, 38%) 1H NMR (CDCI3): 7.97 (dd, J = 4.4, 2.8 Hz, 1 H), 7.95 (d, J = 1 .2 Hz, 1 H), 7.70 (tt, J = 5.7, 2.8 Hz, 1 H), 7.65 (td, J = 8.1 , 4.9 Hz, 1 H), 7.62 – 7.57 (m, 1 H).

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; JANSSEN PHARMACEUTICA NV; CHAI, Wenying; LETAVIC, Michael, A.; LY, Kiev, S.; PIPPEL, Daniel, J.; RUDOLPH, Dale, A.; SAPPEY, Kathleen, C.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; SOYODE-JOHNSON, Akinola; STOCKING, Emily, M.; SWANSON, Devin, M.; WO2011/50198; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 7343-34-2, name is 3,5-Dimethyl-4H-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. 7343-34-2

A mixture containing 1-fluoro-4-nitrobenzene (282 mg), 3,5-dimethyl-1H-1,2,4-triazole (194 mg), potassium carbonate (552 mg)and DMF (6 mL) was stirred at 80 C. overnight. The reaction mixture was cooled to room temperature and ethyl acetate was then added thereto, and washing with water was performed. The organic layer was dried over anhydrous sodium sulfate and concentrated under a reduced pressure, and thereby 3,5-dimethyl-1-(4-nitrophenyl)-1H-1,2,4-triazole (330 mg) was obtained.

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 7343-34-2.

Reference:
Patent; RIKEN; THE UNIVERSITY OF TOKYO; HASHIZUME, Yoshinobu; SEKIMATA, Katsuhiko; KUBOTA, Hirokazu; YAMAMOTO, Hirofumi; KODA, Yasuko; KOYAMA, Hiroo; TAGURI, Tomonori; SATO, Tomohiro; TANAKA, Akiko; MIYAZONO, Kohei; (156 pag.)US2019/337926; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

956317-36-5, The chemical industry reduces the impact on the environment during synthesis 956317-36-5, name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, I believe this compound will play a more active role in future production and life.

The 5-methyl-2 – (2H-1, 2, 3-triazole-2-yl) benzoic acid (2.03g, 10mmol) is added to the 100 ml round bottom flask in the single port, with anhydrous dichloromethane (20 ml ) is dissolved, and then sequentially slowly adding thionyl chloride (15 ml, 200mmol) and pyridine (0.15 ml, 2mmol), the resulting reaction mixture is gradually heated up to reflow, reaction 3 hours. Stop reaction, to be reacted after cooling to room temperature, solvent evaporating under reduced pressure, the resulting crude product does not pass through the purification, the reaction proceeding to the next step directly.

The chemical industry reduces the impact on the environment during synthesis 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Guangdong East Sunshine Pharmaceutical Co., Ltd.; Jinchuan, Fei; Gao, Heng; Zhang, Ji; Zhang, Yingjun; (84 pag.)CN105461699; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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 93 Preparation of 4-(3-Methyl-1H-1,2,4-triazol-1-yl)benzaldehyde (DI53) To a stirring solution of 4-fluorobenzaldehyde (5.0 g, 40.32 mmol) in DMF (50 mL), were added K2CO3 (3.34 g, 40.32 mmol) and 3-methyl-1,2,4-trizole (3.34 g, 40.32 mmol) and the resultant reaction mixture was stirred at ambient temperature for 4 h. After completion of the reaction (TLC), the reaction mixture was diluted with water and extracted with EtOAc (3¡Á). The combined EtOAc layer was washed with water and brine then dried over Na2SO4 and concentrated under reduced pressure to afforded the title compound as a white solid (4.1 g, 60%): mp 125-128 C.; 1H NMR (400 MHz, CDCl3) delta 10.05 (s, 1H), 8.76 (s, 1H), 8.02 (d, 2H), 7.85 (d, 2H), 2.50 (s, 3H); ESIMS m/z 188.04 ([M+H]+).

The chemical industry reduces the impact on the environment during synthesis 7170-01-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US9211280; (2015); B2;,
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. 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, This compound has unique chemical properties. The synthetic route is as follows., 41253-21-8

To 1.5 kg of crude alpha,alpha,alpha’,alpha’-tetramethyl-5-bromomethyl-1,3-benzene-diacetonitrile 5 (purity > 80%, about 3 mol) in 7.5 1 DMF 0.275 kg 1,2,4-triazole sodium (3 mol) were added. The mixture was stirred at room temperature for 1 hr. After completion, 10 1 ethyl acetate and 25 1 water were added. The mixture was stirred for about 10 minutes and then phase separated. To the aqueous layer 5 1 ethyl acetate were added. The mixture was stirred for about 10 minutes and then phase separated. The aqueous layer was discarded, and the organic layers were combined. The combined organic layers were washed with 10 1 water twice. The organic layer was concentrated to dryness to obtain the crude anastrozole 6 (90 %, purity > 60%). The crude product was purified by flash column chromatography (silica) using ethyl acetate as eluent (purity > 98%). Finally, the pre-purified anastrozole was re-crystallised from ethyl acetate/cyclohexane (1:2) to obtain 6 with a purity of more than 99.9%. Yield 34 %.

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; Helm AG; EP1705168; (2006); 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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., 7411-23-6

a. Potassium carbonate, 16.6 g (0.12 mol), was added to a solution of 25.0 g (0.11 mol) of triazole 1 in 400 mL of acetone. The suspension was stirred for15 min at 20 C, 12.7 g (0.10 mol) of benzyl chloride was added, and the mixture was refluxed for 8 h with stirring. The solvent was distilled off, and the light yellow oily residue was treated with 200 mL of water.The mixture was stirred for 5 min, and crystals precipitated and were filtered off and recrystallized from hexane. Yield 22.3 g (64 %).

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; Tolstyakov; Russian Journal of Organic Chemistry; vol. 54; 10; (2018); p. 1537 – 1547; Zh. Org. Khim.; vol. 54; 10; (2018); p. 1525 – 1534,10;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 288-36-8 name is 1H-1,2,3-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. 288-36-8

But-3-yn-1-ol (49.57 g, 707.2 mmol) and triethylamine (107.7 mL, 777 mmol, dried over KOH) were dissolved in dry dichloromethane (500 mL) under a nitrogen atmosphere and cooled to 0 C. Methanesulfonyl chloride (54.8 mL, 708 mmol), dissolved in 500 mL of dry dichloromethane was added within 90 minutes while keeping the temperature below 5 C. The mixture was stirred for 3.5 hours at room temperature, then poured onto 2.5 L of ice water. The organic phase was separated and washed with 2¡Á500 mL of water and 1¡Á250 mL of brine and dried over sodium sulfate. The volatiles were removed to yield 94.18 g of the methane sulfonate (631.2 mmol, 89.2%) as a yellow liquid. A suspension of NaOH (37.86 g, 946.5 mmol), sodium iodide (94.65 g, 631.5 mmol) and 1H-[1,2,3]Triazole (61.03 g, 883.6 mmol) in 2-methyl-2-butanol (750 mL) was refluxed for 1 h under an inert atmosphere. After cooling to room temperature the methane sulfonate (94.18 g, 631.2 mmol) was added within 5 minutes. The resulting suspension was then heated to reflux for 3 hours, cooled to room temperature and concentrated on a rotary evaporator at 45 C. Water (500 mL) and dichloromethane (1 L) were added and the organic phase was separated, dried over sodium sulfate and the volatiles removed at 30 C. The residue was distilled at 1.5 mbar. A forerun was collected at 20-70 C. The main fraction distilled at 123-129 C. as a colorless, turbid liquid. After filtration over Celite (a pad of diatomite) 1-But-3-ynyl-1H-[1,2,3]triazole was obtained as a colorless liquid (29.8 g, 40%). The content according to GC/FID was >98%. -H-NMR (CDCl3) delta=2.05 (t, 1H, C?CH), 2.75 (dt, 2H, CH2-C?CH), 4.5 (t, 2H, CH2-triazole), 7.65 (s, 1H, triazole), 7.70 (s, 1H, triazole).

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

Reference:
Patent; Bossenmaier, Birgit; Friebe, Walter-Gunar; Friess, Thomas; Kling, Lothar; Rueth, Matthias; Voss, Edgar; US2005/203064; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7411-23-6, 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. 7411-23-6 name is 3,5-Dibromo-1H-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.

Sodium hydride (34 mg, 0.86 mmol) was slowly added to a solution of 3,5-dibromo-1H-1,2,4-triazole (150 mg, 0.66 mmol) and DMF (3.9 mL) at RT and the solution was stirred at 45C for 30 min. tert-butyl 4-methylsulfonyloxypiperidine-1-carboxylate (0.15 mL, 0.79 mmol) was then added portion-wise. The reaction mixture was stirred at 85 C for 2 days. The reaction was quenched with NH4Cl (aq. sat.) and extracted with DCM. The combined organic fractions were dried via a phase separator and reduced in vacuo. The crude residue was dissolved in DCM, reduced in vacuo onto silica and purified by silica flash chromatography eluting with 10-90% EtOAc in Pet. Ether to yield tert-butyl 4-(3,5-dibromo-1,2,4-triazol-1-yl)piperidine-1-carboxylate (140 mg, 0.34 mmol, 52% yield) as a pale yellow oil. UPLC-MS (ES+, Method A): 1.82 min, m/z 411.0 [M+H]+.

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

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, molecular formula is C3H5N3, 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. 7170-01-6.

5-Methyl-1-(4-nitrophenyl)-1H-1,2,4-triazoleGeneral procedure C: Preparation of 3- or 5-substituted-1-(4-nitrophenyl)-1H-1,2,4- triazole.[0115] A mixture of 4-fluoro-l -nitrobenzene (0.28 g, 2.0 mmol), 3-methyl-1H-1,2,4-triazole (0.18 g, 2.2 mmol), K2CO3 (0.55 g, 4.0 mmol) and DMF (2 mL) was heated at 70 C overnight. The reaction mixture was cooled down to room temperature, diluted with water, extracted with EtOAc (3x). The organic solution was dried over anhydrous MgSO4 and concentrated in vacuo to provide a solid. Purification of this material by column chromatography on silica gel (40% EtOAc / hexane) provided 3-methyl-1-(4-nitrophenyl)- 1H-1,2,4-triazole as the major product. 1H NMR (CDCl3, 400 MHz) delta 8.59 (s, 1H), 8.39 (d, 2H), 7.88 (d, 2H), 2.53 (s, 3H). Further elution with 65% EtOAc / hexane provided 5-methyl- l-(4-nitrophenyl)-1H-1,2,4-triazole as the minor product. 1H NMR (CDCl3, 400 MHz) delta 8.34 (d, 2H), 7.93 (s, 1H), 7.66 (d, 2H), 2.59 (s, 3H).

The synthetic route of 3-Methyl-1H-1,2,4-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE SCRIPPS RESEARCH INSTITUTE; WO2009/32861; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

4928-87-4, 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. 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, A new synthetic method of this compound is introduced below.

General procedure: The tail group amines Ar-NH2 (Ar a-d) (19.5 mmol,1.1 equiv) were added to a stirring solution of 1,2,4-triazole-3-carboxylic acid 12 (2.00 g, 17.7 mmol, 1.0 equiv) in dry DMF(30 mL) at room temperature. After 5 min, TBTU (6.0 g, 18.6 mmol,1.0 equiv) and DIPEA (11.0 mL, 61.9 mmol, 3.5 equiv) were added insequence. The resulting solution was stirred at room temperaturefor 16 h. After completion of the reaction, as indicated by TLC, DMFwas removed by rotary evaporation at 30 torr and 70 C. The crudematerial was purified by methods described in each individualentry.

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; Chakraborty, Amarraj; Dou, Yali; Gibbons, Garrett S.; Grigsby, Sierrah M.; Lee, Young-Tae; Liao, Chenzhong; Mathew, Bini; Moukha-Chafiq, Omar; Nikolovska-Coleska, Zaneta; Pathak, Vibha; Reynolds, Robert C.; Schuerer, Stephan C.; Snowden, Timothy S.; Umeano, Afoma C.; European Journal of Medicinal Chemistry; vol. 189; (2020);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics