Triazoles

7411-23-6, The chemical industry reduces the impact on the environment during synthesis 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life.

10.71 g (50 mmol, 1 eq) of 3,5-dibromo-1,2,4-triazole, 27.22 g (120 mmol, 2.4 eq)4-amino-4′-nitrobiphenyl, 14.4 g (150 mmol, 3 eq)Sodium tert-butoxide was dissolved in 350 mL of toluene.Then 1.8 g (2 mmol, 0.04 eq) of tris(dibenzylideneacetone)dipalladium and 1.19 g (4 mmol, 0.08 eq) of 2-(di-tert-butylphosphine)biphenyl were added to the solution.The above mixed solution was refluxed under nitrogen for 12 h.After the reaction is completed, it is cooled to room temperature for filtration.The filtered solid was dissolved in 300 mL of a mixed solvent of acetone and dichloromethane.The organic layer was washed with 200 mL of a 5% aqueous hydrochloric acid solution.The organic layer was dried over anhydrous magnesium sulfate and concentrated.The obtained crude product was passed through a silica gel column.Purification yielded 18.6 g of intermediate.The yield is 75%,

The chemical industry reduces the impact on the environment during synthesis 3,5-Dibromo-1H-1,2,4-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Fuyang Xinyihua Materials Technology Co., Ltd.; Wu Jingwei; Wang Zhanqi; Guo Linlin; Hong Haozhi; (15 pag.)CN106479518; (2018); B;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

To a solution of 2-fluoro-6-iodobenzoic acid (502.5 mg), copper(I) iodide (36.5 mg), cesium carbonate (1.25 g) and trans-N,N’-dimethylcyclohexane-1,2-diamine (0.047 mL) in N,N-dimethylformamide (2.0 mL) was added 1H-1,2,3-triazole (330.3 mg), and the mixture was stirred at 100 C. for 0.5 hr. To the reaction mixture were added ethyl acetate and water. The obtained aqueous layer was neutralized with 1N aqueous hydrogen chloride solution, and extracted with ethyl acetate. The obtained organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (445.6 mg). MS: [M+H]+ 208.1.

Statistics shows that 288-36-8 is playing an increasingly important role. we look forward to future research findings about 1H-1,2,3-Triazole.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; KAMEI, Taku; ARIKAWA, Yasuyoshi; OHASHI, Tomohiro; IMAEDA, Toshihiro; FUJIMORI, Ikuo; MIKI, Takashi; YONEMORI, Jinichi; OGURO, Yuya; SUGIMOTO, Takahiro; SETO, Masaki; NISHIDA, Goushi; KAMATA, Makoto; IMOTO, Hiroshi; (132 pag.)US2018/155333; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common compound: 61-82-5, name is 1H-1,2,4-Triazol-5-amine, belongs to Triazoles compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 61-82-5

General procedure: A mixture of aldehyde (1.0 mmol), dimedone (1.0 mmol),1H-1,2,4-triazol-3-amine (1.0 mmol) and nano-AlPO4(SO3H) (0.1 g) was stirred in the acetonitrile (4.0 mL)at 50 C for an appropriate time. After the completion of thereaction as indicated by TLC, dichloromethane was addedto the solidified mixture and the insoluble catalyst was separatedby centrifugation. Evaporation of the solvent from thefiltrate and recrystallization of the solid residue from hot ethanolafforded the pure products in good to excellent yields

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, 61-82-5, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sharghi, Hashem; Aboonajmi, Jasem; Aberi, Mahdi; Shiri, Pezhman; Journal of the Iranian Chemical Society; vol. 15; 5; (2018); p. 1107 – 1118;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

Analogous to the general method described in J. Org. Chem. 2004, 69, 8115, and Chem. Pharm. Bull, 1997, 1145. To a 2-necked flask containing 1-methyl-1H-1,2,3-triazole (1.00 g, 12.0 mmol, Intermediate 42, step a) was added THF (75 mL) and the solution was cooled between -40 to -20 C. To this colorless homogeneous solution was added n-BuLi (2.5 M in hexanes, 5.0 mL, 11.4 mmol) dropwise which afforded a dark brown viscous mixture. After stirring at 0 C. for 1 hours, a THF (10 mL) solution of 4-chlorobenzaldehyde (1.60 g, 11.4 mmol) was introduced and the reaction mixture began to be stirred freely and remained brownish. After 3 hours the reaction mixture was quenched by pouring into a saturated solution of NH4Cl and the aqueous portion was extracted with EtOAc (4¡Á50 mL). The combined organics were washed with brine, dried over MgSO4, filtered and concentrated to give a brown oil which solidified upon standing. The crude material was triturated with Et2O to provide the title compound as a brown solid.

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; Janssen Pharmaceutica NV; 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; Mirzadegan, Taraneh; Ganamet, Kelly; US2014/107097; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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

A mixture of 3 -methyl- IH-1, 2,4-triazole (8.12 g, 98 mmol), l,2,3-trifluoro-5-nitrobenzene (17.3 g, 98 mmol), and sodium bicarbonate (8.21 g, 98 mmol) in DMSO (100 mL) was heated at 800C for 24 h . The reaction mixture was allowed to cool to rt and was poured into water (800 mL). The aqueous mixture was extracted with EtOAc (3 x 200 mL). The combined organic extracts were sequentially washed with water (500 mL) and brine solution (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude reaction mixture was purified using silica gel chromatography (30-80% EtOAc/hexane, linear gradient) to afford a 1.7:1.0 mixture of two regioisomeric products as an orange solid. The orange solid was recrystallized from EtOAc (hot- cold) to provide 4.25 g of l-(2,6-difluoro-4-nitrophenyl)-3-melhyl-lH-l.,2,4-triazole as a white solid. The mother liquor was recrystalized from EtO Ac/Hex (hot-rt) to afford 1.89 g of l-(2,6-difluoro-4-nitrophenyl)-5-methyl-lH-l,2,4-triazole as a light yellow solid. The mother liquor was repeatly chromatographed under the previously stated conditions to provide two samples. One sample was partially enriched in the slightly less polar isomer, l-(2,6-difluoro-4~nitrophenyl)-3-memyl-lH-l,2,4-t?azole. The other sample was partially enriched in the slightly more polar isomer, l-(2,6- difluoro-4-nitrophenyl)-5-methyl-lH-l,2,4~triazoe. Both samples were independently recrystallized from EtO Ac/Hex to provide an additional 1.9 g of 1- (2,6-diiluoro-4-nitrophenyl)-3 -methyl- 1 H- 1 ,2,4-triazole and 1.37 g of l-(2,6- difluoro-4-nitrophenyl)-5-methyl- 1 H- 1 ,2,4-triazole. A combined total of 6.15 g (26 % yield) of 1 -(2,-difluoro-4-nitrophenyl)~3-methyl-l H- 1 ,2,4-triazole and 3.2 g (13% yield) of l-(2,6-difluoro-4-nitrophenyl)-5-methyl- IH-1 ,2,4-triazole was obtained.Data for 1 -(2 s6-difluoro-4-nitrophenyl)-3 -methyl- 1 H- 1 ,2,4-triazole: LC-MS(M+H)+ = 241.0. 1H NMR (500 MHz, CHLOROFORM-d) delta ppm 8.34 (s, 1 H), 8.01- 8.10 (m, 2 H)5 2.54 (s, 3 H). Data for l-(2,6-difluoro-4-nitrophenyl)-5-methyl-lH-l,2,4-triazole: LC-MS(M+H)+ = 241.0. IH NMR (500 MHz, CHLOROFORM-d) delta ppm 8.08 (s, 1 H)5 8.04- 8.08 (m, 2 H), 2.45 (s, 3 H). An X-ray analysis of a single crystal grown from EtOAc/hexanes confirmed the regiochemical assignment of this isomer as the 5- methyl congener.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyl-1H-1,2,4-triazole, its application will become more common.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7343-33-1, name is 5-Bromo-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. 7343-33-1

General procedure: To a reaction vial were added 2-bromo-5-(trifluoromethoxy)pyridine ( 1.0 g, 4.1 mmol) and 3-bromo- l – -l,2,4-triazole (0.91 g, 6.2 mmol). Lambda ,/V-Dimethylformamide (16 ml_) and cesium carbonate (2.6 g, 8.2 mmol) were added, and the vial was degassed for 5 minutes with argon. Copper(I) iodide (0.077 g, 0.41 mmol) was added, and the via l was further degassed for 5 minutes with argon. The vial was capped and heated at 100 C for 1 hour in a Biotage Initiator microwave reactor, with external IR-sensor temperature monitoring from the side of the vessel. The reaction mixture was cooled to room temperature, poured onto crushed ice (3 volumes), and extracted with ethyl acetate (3 x 150 ml_). The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography using 0-40% ethyl acetate/hexanes as eluent provided the title compound as a pale brown liquid (0.40 g, 31%) : *H N MR (400 MHz, CDCI3) delta 9.01 (s, 1H), 8.39 (d, J = 2.4 Hz, 1H), 7.94 (d, J = 8.8 Hz, 1H), 7.77 (dd, J = 1.6 Hz, 8.8Hz, 1H) ; ESIMS m/z 309 ([M + H]+).

Statistics shows that 7343-33-1 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-1H-1,2,4-triazole.

Reference:
Patent; DOW AGROSCIENCES LLC; GIAMPIETRO, Natalie C.; CROUSE, Gary D.; SPARKS, Thomas C.; DEMETER, David A.; (242 pag.)WO2017/40742; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

61-82-5, These common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, 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.

General procedure: To a mixture of dimedone (1 mmol), aldehyde (1 mmol), 2-aminobenzimidazole or 3-amino-1,2,4-triazole (1 mmol)and nano-SiO2 (15 mol %) in the acetonitrile (5 mL) was stirred for appropriate time (Table 2) at 25-30 C. After the completion of the reaction as indicated by TLC, dichloromethane (CH2Cl2) was added to the solidified mixture and the insoluble catalyst was separated by filtration. Evaporation of the solvent from the filtrate and recrystallization of the solid residue from hot ethanol afforded the pure products in high yields.

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 61-82-5.

Reference:
Article; Mousavi, Mir Rasul; Maghsoodlou, Malek Taher; Journal of the Iranian Chemical Society; vol. 12; 5; (2015); p. 743 – 749;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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 7170-01-6 as follows. 7170-01-6

41. 5-(3-Methyl-1H-1,2,4-triazole-1-yl)-1,6-naphthyridin-2(1H)-one–A stirred mixture containing 13.5 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 20 g of 3-methyl-1H-1,2,4-triazole and 75 ml of N-methylpyrrolidinone was heated in an oil bath at 170-180 C. for 18 hours and then cooled to room temperature whereupon a tan solid crystallized out. The mixture was diluted by adding 125 ml of water and the separated solid was collected, washed with water, air-dried and combined with another 1.2 g sample of the same material obtained in another run starting with 2.25 g of 5-bromo-1,6-naphthyridin-2(1H)-one. The combined solids were recrystallized from dimethylformamide and dried in an oven at 95-100 C. for three days to yield 6.1 g of 5-(3-methyl-1H-1,2,4-triazole-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. >300 C.

According to the analysis of related databases, 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sterling Drug Inc.; US4634772; (1987); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

1533519-84-4, Adding some certain compound to certain chemical reactions, such as: 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, 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 1533519-84-4.

Example 9. Preparation of phenyl 2-((4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate [074] To a round bottom flask was added 4-(4-cyclopropyl-l-yl)-4H-l, 2,4-triazole-3-thiophenol (40.0 g), isopropanol (620 mL) and triethylamine (16.6 g) to form a mixture at room temperature, after stirred for 20 min, the mixture was cooled to 0C, then was added drop wise a solution of phenyl bromoacetate in isopropanol (33.8 g of phenyl bromoacetate was dissolved in 200 mL of isopropanol), during the addiction the mixture was maintained at about 0C, after the addition, the mixture was warm to 20C, after stirred for about 2 hours, the reaction was complete, filtered, the filter cake was washed with isopropanol (100 mL). The filter cake was added purified water (700 mL) to give a slurry, the slurry was stirred for 1 hour, then the purified water was removed by vacuum filtration, the filter case was dried under vacuum at about 50C for about 24 hours to obtain phenyl 2-((4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate, yield 92%, the HPLC purity (area) 99.0%.

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 1533519-84-4.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CHEN, Weiqiang; LUO, Jian; LIU, Lixue; FAN, Yuping; WO2014/198241; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

1533519-84-4, 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. 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

In a 100 ml three-necked flask equipped with a stirrer and a thermometer, 25 ml of DMF was added, the intermediate (III)2.67 g, stirred at room temperature, 1.45 g of potassium carbonate was added, and 1.61 g of methyl bromoacetate was added dropwise at 25 C,Stirring was continued for 3 hours; 50 ml of water was added and extracted with ethyl acetate 50 ml x3 to combine the organic phase,The ethyl acetate was concentrated and concentrated, and 50 ml of methanol was added thereto. The crystals were recrystallized, filtered and dried to give 3.22 g of product,Namely intermediate (IV), yield 99.5%.

The synthetic route of 1533519-84-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu Baoyu Pharmaceutical Co., Ltd.; Lei, Lang; Li, Shanwei; Xiong, Bo; (10 pag.)CN105906576; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics