Category: 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. Safety of 1H-1,2,3-Triazole

Intermediate 77: 2,3-Dimethoxy-6-[1 ,2,3]triazol-2-yl-benzoic acid.To a 20 ml microwave vial containing 2-bromo-4,5-dimethoxybenzoic acid (3 g, 1 1 .5 mmol), copper iodide (0.04 g, 0.5 mol%), cesium carbonate (7.5 g, 23 mmol), triazole (1 .33 mL, 23 mmol) and finally (R,R)-(-)-N,N’-dimethyl-1 ,2- cyclohexanediamine ligand (0.36 mL, 2.3 mmol) was added DMF (12 mL). The resulting clumpy yellow slurry was stirred until evenly dispersed then heated to 120C for 10-20 min using a microwave. At this point the reaction mixture appeared as a blue slurry which was then diluted with 20 mL ether and 20 mL H20. The resulting solution was thoroughly stirred and transferred to a separatory funnel then the RBF was subsequently rinsed with 20 mL ether and H20 each. The aqueous layer was separated from the organic layer and acidified to pH 1 with 6 mL cone. HCI. The now brown/ lime green aqueous layer was extracted twice with EtOAc. The bright yellow organic layers were combined and dried with Na2S04 and then cone, into a yellow powder under reduced pressure which was purified by FCC (0-5% MeOH in DCM w/ 0.5% AcOH) to afford 2,3-dimethoxy-6-[1 ,2,3]triazol-2-yl-benzoic acid (60%) and 2,3- dimethoxy-6-[1 ,2,3]triazol-1 -yl-benzoic acid (20%). Data for 2,3-dimethoxy-6- [1 ,2,3]triazol-2-yl-benzoic acid, MS (ESI): mass calculated for C-11 H-1 -1 N3O4, 249.23; m/z found 250.3 [M+H]+. 1H NMR (400 MHz, CD3OD): 7.87 (s, 2H), 7.47 (s, 1 H), 7.18 (s, 1 H), 3.94 (s, 3H), 3.91 (s, 3H).

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8, A common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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.

1- (3-CHLORO-PROPOXY)-4-NITRO-BENZENE (7 g, 32.5 mmol) is dissolved in 2-methyl- 2-butanol (35 ml) followed by the addition of 1H-1, 2,3-triazole (3.43 g, 48.7 mmol), potassium iodide (0.54 g, 3.25 mmol) and sodium hydroxide (1.95 g, 48.7 mmol). The mixture is stirred for 20 h at 120 C, evaporated to dryness and suspended in toluene. Washing with water, drying over sodium sulfate and concentration in vacuo yields a crude product, which is washed with ether yielding L- [3- (4-NITRO-PHENOXY)-PROPYL]-LH- [L, 2,3] triazole as a colorless solid. Yield 6 g (75 %) MS: M = 249.3 (API+) H-NMR (400 MHz, CDC13) : 2.48 (m, 2H), 4.07 (t, J = 5.77 Hz, 2H), 4.64 (t, J = 6.7 Hz, 2H), 6.93 (d, J = 9.3 Hz, 2H), 7.56 (s, 1H), 7.72 (s, 1H), 8.20 (d, J = 9.2 Hz, 2H).

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/96796; (2004); 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., category: Triazoles

Intermediate 6: 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid To a solution of 2H-1,2,3-triazole (CAS number 288-36-8; 1.99 g, 28.93 mmol) in DMF (7.0 ml) at 0-10 C. was added cesium carbonate (4.7 g, 14.45 mmol), trans-1-N,2-N-dimethylcyclohexane-1,2-diamine (0.127 g, 1.45 mmol), copper(I) iodide (0.068 g, 0.36 mmol) and 2-iodo-5-methylbenzoic acid (CAS number 52548-14-8; 3.79 g, 14.46 mmol). The reaction was subjected to microwave irradiation at 125 C. for 15 minutes, and then poured into water (20 ml) and extracted with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography (0-3% methanol/DCM) to afford the title compound. 1H NMR (DMSO-d6) delta ppm 2.42 (s, 3H), 7.49-7.52 (m, 1H), 7.58-7.64 (m, 2H), 8.05 (s, 2H), 13.01 (s, 1H). (0444) MS ES+: 204

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; Takeda Pharmaceutical Company Limited; Fieldhouse, Charlotte; Glen, Angela; Maine, Stephanie; Fujimoto, Tatsuhiko; Robinson, John Stephen; US2015/232460; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-36-8, 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.

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 96 h. The reaction was diluted with water, washed with ether, and acidified with cone. HC1. The acidic aqueous solution was extracted 3x with EtOAc 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 EtOAc) in hexanes], to provide Intermediate C as a solid. LRMS m/z (M+H) 196.2 found, 196.1 required.

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, 1H-1,2,3-Triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; REGER, Thomas, S.; SKUDLAREK, Jason, W.; (0 pag.)WO2016/85784; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 288-36-8,Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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.

The molar ratio of 9,10-dibromoanthracene: 1H-1,2,4-triazole: potassium carbonate: copper oxide is 2: 10-15: 30: 1In the magnet,A 50 mL three-necked round bottom flask equipped with a reflux condenser and a thermometer was charged with CuO (0.0398 mg, 0.5 mmol)Potassium carbonate (2.0731 g, 15 mmol),Triazole (0.345 mg, 5 mmol),9,10-dibromoanthracene (0.3360 g, 1 mmol),20 mL DMF.Start stirring at 100 oC,Reaction for 24 hours.After the reaction,The reaction solution was cooled to room temperature,Filtration, the filtrate was added 100 mL of water,Precipitation precipitation, filtration,The filter cake was collected in a yield of 60%.

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

Reference:
Patent; Tianjin Normal University; Wang Zhongliang; Yang Xi; Guo Changcheng; Shang Yuntao; Zhang Zhigang; Wang Ying; (11 pag.)CN106188104; (2016); A;,
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., Formula: C2H3N3

To a mixture of 2-bromo-4-fluorobenzoic acid (30 g, 137 mmol), cesium carbonate (89.26 g, 274 mmol) and Cul (5.27 g, 27.4 mmol) in DMF (200 mL) were added N,N’-dimethylcyclohexane-1,2-diamine (3.7 mL,23.3 mmol) and 1H-1,2,3-triazole (18.92 g, 274 mmol). The resulting mixture was stirred at 110C overnight, cooled, concentrated in vacuo and diluted with water (150 mL). The aqueous layer was extracted with EtOAc (300 mL x 3). The aqueous layer was acidified with 2N HCl and extracted with EtOAc (300 mL x 4). The combined organic layers were washed with brine (150 mL x 3), dried over Na2SO4, filtered andthe filtrate concentrated in vacuo. The residue was purified by chromatography on silica gel (petroleum ether : EtOAc = 100: 1 ~ 5 : 1) to provide the title compound as a yellow solid. LRMS m/z (M+H) 208.0 found, 208.0 required.

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.; LIVERTON, Nigel; BESHORE, Douglas C.; KUDUK, Scott D.; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/18027; (2015); A1;,
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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1H-1,2,3-Triazole

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, 114 mg (0.60 mmol) CuI and 310 mg (2.17 mmol) trans-N,N’-dimethylcyclohexane-1,2-diamine. The mixture was heated at 120 C. 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 (MeOH in DCM with 0.1% AcOH) to give the faster eluting desired 2-(2H-1,2,3-triazol-2-yl)benzoyl acid, A-1. Data for A-1: 1HNMR (500 MHz, DMSO-d6) delta 13.05 (br s, 1H), 8.12 (s, 2H), 7.81-7.52 (m, 4H) ppm. The undesired 2-(1H-1,2,3-triazol-2-yl)benzoic acid eluted second.

According to the analysis of related databases, 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bergman, Jeffrey M.; Breslin, Michael J.; Coleman, Paul J.; Cox, Christopher D.; Mercer, Swati P.; Roecker, Anthony J.; US2008/132490; (2008); A1;,
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. 288-36-8, name is 1H-1,2,3-Triazole, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C2H3N3

In the reactor,Add 90% acetone (volume fraction) 400mL,Stirring,26.2 g of compound (01)Then 34.5 g of potassium carbonate powder was added,0.38 g copper iodide (CuI),1,2,3-triazole.External temperature was raised to 70 ,During the heating process, a large amount of gas is generated,The reaction was stirred at reflux for 5 hours.The reaction mixture was then distilled under reduced pressure at 40 C,When the reaction system is more viscous, add 45mL of water and continue to reduce the steam to distillate without acetone (no acetone in the gas phase). Distilled residue was added 300mL of water, 25% sulfuric acid was added dropwise at room temperature to adjust the pH to 1-2, a yellow suspension.Stir for 30 minutes, filter, and the solids are washed three times with water, 60 mL each. The resulting solid was dried to dryness at 70 C in vacuo,Have pale green solid 19.48g,Compound (1), purity 95.06%.

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; He Bifei; Liu Guangyuan; Fan Yuping; (6 pag.)CN104557744; (2017); B;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8, 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.

To a 100 ml round bottom flask containing 2-chloro-6-methylnicotinic acid (3 g, 17.4 mmol), copper iodide (0.16 g, 0.5 mol%), and cesium carbonate (1 1 .4 g, 35 mmol) was added a mixture of dioxane (20 ml_) and H2O (0.1 ml, 5.25 mmol). Next triazole (2.03 ml_, 35 mmol) and finally (R,R)-(-)-N,N’-dimethyl-1 ,2- cyclohexanediamine ligand (0.56 ml_, 3.5 mmol) were added. The resulting clumpy yellow slurry was stirred until evenly dispersed. Upon heating to 100C the reaction mixture changed from a yellow slurry to pale green. As heating progressed the slurry became less thick and was stirred more easily. The light green slurry was stirred for 4 hr at 100C and left to stir at room temp overnight. At this point the reaction mixture appeared as a cobalt blue slurry which was then diluted with 20 ml_ ether and 20 ml_ H2O. The resulting solution was thoroughly stirred and transferred to a seperatory funnel then the RBF was subsequently rinsed with 20 ml_ ether and H2O each. The aqueous layer was separated from the organic layer and acidified to pH 1 with 6 ml_ cone. HCI. The now brown/ lime green aqueous layer was extracted twice with EtOAc. The bright yellow organic layers were combined and dried with Na2SO and then cone, into a yellow powder under reduced pressure. To the yellow powder was added EtOAc to form a yellow slurry. The solids were filtered off and washed with EtOAc to give a very pale yellow powder, which was found by 1H NMR to be Intermediate 53 (25% yield). The filtrate was cone, into a yellow solid and purified by FCC using 0-5% MeOH in DCM w/ 0.5% AcOH to give the title compound in a 20% yield. MS (ESI): mass calculated for C9H8N4O2, 204.18; m/z found 205.3 [M+H]+. 1 H NMR (400 MHz, CD3OD): 8.21 – 8.18 (m, 1 H), 7.98 (s, 2H), 7.51 (d, J = 7.9 Hz, 1 H), 2.64 (s, 3H).; Intermediate 51 : 6-Methyl-2-[1 ,2,3]triazol-1 -yl-nicotinic acidThe title compound was isolated from the procedure used to prepareIntermediate 47 with a 25% yield. MS (ESI): mass calculated for Omicron9Eta8Nu4Omicron2, 204.18; m/z found 205.3 [M+H]+ 1H NMR (400 MHz, CD3OD): 8.48 (d, J = 1 Hz, 1 H), 8.25 (dd, J = 7.9, 3.8 Hz, 1 H), 7.88 (d, J = 1 .1 Hz, 1 H), 7.54 (d, J = Hz, 1 H), 2.64 (s, 3H).

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

Reference:
Patent; JANSSEN PHARMACEUTICA NV; BRANSTETTER, Bryan, James; LETAVIC, Michael, A.; LY, Kiev, S.; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; WO2011/50200; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 288-36-8,Some common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, molecular formula is C2H3N3, 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 mixture of the product from step 2 (7.9 g, 38 mmol), cesium carbonate (24.8 g,76 mmol) and CuI (2.88 g, 7.6 mmol) in DMF (200 mL) were added 2H-[1,2,3]triazole (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 110 C overnight. The cooled reaction mixture was adjusted to ~pH 12 with IM sodium hydroxide and extracted with EtOAc (50 mL x 3). The aqueous layer was adjusted to ~pH 4 with IM HCl and extracted with EtOAc (50 mLx4). The extracts was dried over Na2S04, filtered, the filtrate concentrated in vacuo and the residue purified by chromatography on silica (Petroleum ether : EtOAc =10: 1) to provide the title compound (4.1 g). LRMS m/z (M+H) 196.0 found, 196.0 required.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; BESHORE, Douglas, C.; KUDUK, Scott, D.; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/20930; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics