Category: Triazoles

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

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

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

A round bottom flask equipped with magnetic stirrer bar was charged with 5-methyl-2- (2H-1,2,3-triazole-2-yl)benzoic acid (2.0 g, 9.4 mmol, 1 equiv), CH2C12 (94 mL) and hexafluoro isopropanol (1.57 g, 9.4 mmol, 1.0 equiv). After addition of EDC hydrochloride (1.79 g, 9.4 mmol, 1.0 equiv) and DMAP (0.23 g, 1.87 mmol, 0.2 equiv), the reaction mixture was stirred at ambient temperature for 1 h. The solvent was evaporated underreduced pressure followed by purification of the crude product by column chromatography (Si02, cyclohexane /ethyl acetate 50:1). 1,1,1,3,3,3 -hexafluoropropan-2-yl 5 -methyl-2-(2H-1 ,2,3-triazole-2-yl)benzoate (2.5 g, 75%) was obtained as a yellowish oil, which solidifies at 2 C to 4 C.?H NMR (500 MHz, d6-DMSO) oe = 8.08 (s, 2H), 7.81 (d, J = 8.25 Hz, 1H), 7.70 – 7.65 (m, 1H), 7.64 – 7.61 (m, 1H), 6.99 (sept, J = 6.28 Hz, 1H), 2.46 (s, 3H)?3C NMR (125 MHz, CDC13) oe = 163.8, 139.8, 137.2, 135.8, 134.8, 130.5, 134.6, 123.3,120.9 (q, J = 238.3 Hz, (CF3)2), 67.1 (sept, J = 33.5 Hz, OCH(CF3)2), 20.8

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 956317-36-5.

Reference:
Patent; SANDOZ AG; HOeFERL-PRANTZ, Kathrin; BARTH, Roland; RICHTER, Frank; ZUPANCIC, Borut; (126 pag.)WO2016/20403; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 288-36-8

To a stirred solution of EE-1 (10 g, 144.79 mmol) in water (100 mL) is added EE-2 (13.73 g, 173.75 mmol) dropwise at 0 C and the reaction mixture is stirred at 0 C for 7 hours. The reaction mixture is filtered and extracted with diethyl ether. The combined organics are concentrated in vacuo to yield EE-3.

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-1,2,3-Triazole.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HUGHES, Robert Owen; LI, Xiang; NEMOTO, Peter Allen; SMITH KEENAN, Lana Louise; WU, Lifen; XIONG, Zhaoming; (65 pag.)WO2018/111803; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 7170-01-6

For the preparation of [Zn(atz)2]¡¤guest (MAF-66), 73 mg of 3-amino-1,2,4-triazole (atz) was dissolved in 50 mL of isopropylalcohol and 40 mg of Zn(OH)2 was dissolved in 50 mL of a 25% aqueous ammonia solution. The solutions were mixed together and stirred for several minutes. The final solution was left at room temperature for 3 d to evaporate slowly. The obtained colorless crystals were centrifuged and washed three times with water and isopropyl alcohol, and then air-dried. Elem. Anal. Calcd. (%) for C7H15.2N8O1.6Zn ([Zn(atz)2]¡¤0.6H2O¡¤1.0C3H8O): C, 27.80; H, 5.07;N, 37.05; Zn, 21.62. Found: C, 27.83; H, 4.86; N, 37.02; Zn, 22.77.

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:
Article; Kim, Han-Ung; Babu, Robin; Roshan, Roshith; Park, Dae-Won; Applied Catalysis A: General; vol. 538; (2017); p. 59 – 65;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-88-0, name is 1H-1,2,4-Triazole, belongs to Triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 288-88-0

General procedure: A mixture of 4-fluoro acetophenone/4-fluorobenzaldehyde (10 mmol) and imidazole/triazole (10 mmol) were dissolved in dry DMF (20 mL). K2CO3 (12 mmol) was added in small portion within a period of 15 min to the above stirred solution. Mixture was stirred for 10-12 h at 110 C. Heating discontinued, K2CO3 was filtered off, filtrate extracted with ethyl acetate (3 ¡Á 15 mL). Organic layer was washed with water (3 ¡Á 15 mL), dried over anhydrous sodium sulphate and concentrated to given an oil which was purified on silica gel column (60-120 mesh) taking methanol: chloroform (1:99) as an eluent.

Statistics shows that 288-88-0 is playing an increasingly important role. we look forward to future research findings about 1H-1,2,4-Triazole.

Reference:
Article; Marrapu, Vijay K.; Chaturvedi, Vinita; Singh, Shubhra; Singh, Shyam; Sinha, Sudhir; Bhandari, Kalpana; European Journal of Medicinal Chemistry; vol. 46; 9; (2011); p. 4302 – 4310;,
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. 288-36-8, name is 1H-1,2,3-Triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. 288-36-8

To a mixture of (2-iodophenyl)methanol [5159-41-1] (1.50 g, 6.41 mmol), 1 H-1 ,2,3-triazole (0.797 g, 11.54 mmol), trans-N, N’-dimethylcyclohexane-l ^-diamine [68737-65-5] (0.091 g, 0.641 mmol) and Cs2C03 (3.76 g, 1 1.54 mmol) in DMF (15 mL), Cul (0.61 g, 3.20 mmol) was added and the reaction mixture was stirred for 20 min at 120C and 15 min at 160C in the microwave. The reaction mixture was cooled to rt and filtered to remove the solids. The filtrate was concentrated under reduced pressure. The residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane) to yield the title compound (1.46 g, 64%). [1H NMR (400 MHz, DMSO-cfe) USD ppm 8.10 (s, 2 H), 7.74 (d, J=7.53 Hz, 1 H), 7.61 (dd, J=8.03, 1.25 Hz, 1 H), 7.52 (td, J=7.53, 1.25 Hz, 1 H), 7.44 (m, 1 H), 5.26 (t, J=5.40 Hz, 1 H), 4.59 (d, J=5.02 Hz, 2 H); LCMS RtA = 0.68, [M+H]+ = 176.1].

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

Reference:
Patent; NOVARTIS AG; BADIGER, Sangamesh; BEHNKE, Dirk; BETSCHART, Claudia; CHAUDHARI, Vinod; COTESTA, Simona; HINRICHS, Juergen Hans-Hermann; OFNER, Silvio; PANDIT, Chetan; WAGNER, Juergen; WO2011/76747; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-34-2, 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 7343-34-2 as follows.

In a 25 mL round-bottomed flask under N2 at 0 ¡ãC, sodium hydride (60percent in mineral oil, 0.059 g, 1.48 mmol) was added to a solution of 3,5-dimethyl-lH-l,2,4-triazole (0.112 g, 1.15 mmol) in DMF (5 mL) and the mixture was stirred for 30 min. To this mixture was then added 5-bromo-4′-(bromomethyl)-[l, r-biphenyl]-2-carbonitrile (1-002, 0.407 g, 1.16 mmol) and the mixture was stirred at RT for 3.5 h. The resulting mixture was then poured into H20 and the product was extracted with EtOAc (x3). The combined organic extract was washed with 0 (x3) and brine, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified on ISCO using a 40 g column (0-5percent MeOH-DCM) to afford the title compound (0.248 mg, 0.675 mmol, 59percent yield) as a colorless gum. LC (Method B): 1.795 min. MS (APCI): calcd for Ci8H16BrN4 [M + H]+ m/z 367.1, found 367.0. H NMR (400 MHz, CDC13) delta ppm 7.66 (dd, J = 0.78, 1.57 Hz, 1H), 7.61 – 7.63 (m, 2H), 7.51 – 7.56 (m, 2H), 7.28 – 7.31 (m, 2H), 5.29 (s, 2H), 2.42 (s, 3H), 2.38 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7343-34-2, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITE DE MONTREAL; BRISTOL-MYERS SQUIBB COMPANY; PRIESTLEY, Eldon, Scott; REZNIK, Samuel, Kaye; RUEDIGER, Edward, H.; GILLARD, James, R.; HALPERN, Oz, Scott; JIANG, Wen; RICHTER, Jeremy; RUEL, Rejean; TRIPATHY, Sasmita; YANG, Wu; ZHANG, Xiaojun; (642 pag.)WO2018/5591; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

6523-49-5, 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. 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, A new synthetic method of this compound is introduced below.

To a solution of Intermediate 18 (60mg, 0.18mmol) in acetic acid (ImI) was added 4- triazolylaniline (35mg, 0.22mmol) and the solution was stirred at 8O0C over 2 hours. LCMS analysis showed consumption of starting material. Reaction mixture was cooled and the excess acetic acid removed by evaporation under reduced pressure. The residues were treated with sat. aq. Sodium hydrogen carbonate until cessation of effervescence. The resulting precipitate was filtered and the solids obtained dried under vacuum. Purification by preparative chromatography furnished the desired compound as an off- white solid (18mg, 22%)1H NMR (D6-DMSO) 10.21 (IH, bs), 9.07 (IH, s), 8.57 (IH, s), 8.42 (IH, s), 8.04 (IH, s), 8.00 (IH, dd, J 8.75Hz, 1.5Hz), 7.90 (2H, d, J 9Hz), 7.72 (IH, s), 7.68 (2H, d, J 3.25Hz), 7.27 (2H, s), 6.96 (IH, d, J 9Hz), 4.53 (IH, quin, J 6Hz), 3.64 (3H, s), 1.12 (6H, d, J 6.25Hz) LC-MS rt 2.48 m/z 454 ES+

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