Category: 288-36-8

Related Products of 288-36-8, New Advances in Chemical Research in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 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, below Introduce a new synthetic route.

To a mixture of 2-bromo-4-fluorobenzoic acid (30 g, 137 mmol), cesium carbonate (89.26 g, 274 mmol) and CuI (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 110 oC 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 and the 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 solid. LRMS m/z (M+H) 208.0 found, 208.0 required.

In the meantime we’ve collected together some recent articles in this area about 1H-1,2,3-Triazole to whet your appetite. Happy reading!

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; LIVERTON, Nigel; LUO, Yunfu; (68 pag.)WO2016/89721; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 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. Recommanded Product: 288-36-8

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1,2,3-triazole (2.1 g, 30.5 mmol), CsCO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dimethylcyclohexane-1,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 C. for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with 1N HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-1,2,3-triazol-2-yl)-5-methylbenzoic acid A-2, followed by the undesired regioisomer isomer, 2-(1H-1,2,3-triazol-2-yl)-5-methylbenzoic acid. Data for A-2: 1HNMR (500 MHz, DMSO-d6) delta 12.98 (br s, 1H), 8.04 (s, 2H), 7.72-7.45 (m, 3H), 2.41 (s, 3H) ppm.

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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

Reference of 288-36-8, New Advances in Chemical Research in 2021.In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 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, below Introduce a new synthetic route.

Synthesis of 5-methyl-2-(2H-l,2,3-triazol-2-yl)benzoyl chloride 14 15 16To a solution of 2-iodo-5-methylbenzoic acid (14, 4.00 g, 15.3 mmol) in DMF (10 mL) was added 1,2,3-triazole (2.10 g, 30.5 mmol), cesium carbonate (9.95 g, 30.5 mmol), copper(I) iodide (0.145 g, 0.76 mmol) and trans -N,N’-dimethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 C for 10 min in a microwave reactor. The reaction was cooled to room temperature, diluted with water, and washed with EtOAc. The aqueous phase was acidified with 1 NHC1 and extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The resultant residue was purified by silica gel chromatography (MeOH:DCM with 0.1% AcOH = 0: 1 to 1 :9) to give the faster eluting 2- (2H-l ,2,3-triazol-2-yl)-5-methylbenzoic acid (15), followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid (16).

This is the end of this tutorial post, and I hope it has helped your research about 288-36-8!

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott, D.; DI MARCO, Christina; WO2013/59163; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 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. Application In Synthesis of 1H-1,2,3-Triazole

A solution of 2-iodo-5-methylbenzoic acid (4.0 g, 15.3 mmol) in DMF (10 mL) was treated with 1 ,2,3-triazole (2.1 g, 30.5 mmol), CsCO3 (9.95 g, 30.5 mmol), CuI (0.145 g, 0.76 mmol) and trans-N,N’-dirnethylcyclohexane-l,2-diamine (0.43 g, 3.05 mmol). The mixture was heated at 120 0C for 10 min in a microwave reactor. The reaction was cooled to rt, diluted with water, and washed with EtOAc. The aqueous phase was acidified with IN HCl and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by gradient elution on SiO2 (0 to 50% EtOAc in water with 0.1% TFA) to give the desired A-3. A portion of this acid (0.1 1 g, 0.53 mmol) was treated with thionyl chloride (0.59 g, 5.3 mmol) in dichloromethane (5.0 mL) at rt. After stirring at RT for 1 h, the mixture was concentrated, azeotroping with benzene to yield acid chloride A-3.

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 1H-1,2,3-Triazole, in my other articles.

Reference:
Patent; MERCK & CO., INC.; WO2009/11775; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 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

DMF (1.5 ml) was added to a mixture of methyl S-iodo-beta-methyl-l-pyridinecarboxylate D36 (100 mg), lH-l,2,3-triazole (49.9 mg, 0.722 mmol), (lR,2R)-N,N’-dimethyl-l,2- cyclohexanediamine (10.27 mg, 0.072 mmol), CuI (3.44 mg, 0.018 mmol) and Cs2CO3 carbonate (235 mg, 0.722 mmol) in a microwave vial. The mixture was degassed via three vacuum/nitrogen cycles then irradiated in a single mode microwave reactor to 120 0C for 20 minutes. The mixture was irradiated in a single mode microwave reactor to 120 0C for a further 40 minutes. The reaction mixture was cooled and filtered washing the solids with EtOAc. The solids were dissolved in pH = 3 buffer solution (5 ml); UPLC check of this aqueous solution showed it contained a considerable quantity of 6-methyl-3-(2H- l,2,3-triazol-2-yl)-2-pyridinecarboxylic acid. The aqueous phase was extracted repeatedly with DCM; the combined DCM extracts were diluted with MeOH (50 ml) and treated with TMS-diazomethane. The volatiles were evaporated to give a yellow residue that was purified by flash chromatography on silica gel (Biotage, SNAP 1O g column, 10 %-50 % EtOAc/Cy) to give the title compound D39 (38 mg) as a white solid. UPLC (BasicQC_POS_50-800): rt = 0.57 minutes, peak observed: 219 (M+l). C10H10N4O2 requires 218. 1H NMR (400 MHz, CDCl3) delta ppm 8.20 (d, 1 H), 7.87 (s, 2 H), 7.44 (d, 1 H), 3.94 (s, 3 H), 2.71 (s, 3 H)

If you are hungry for even more, make sure to check my other article about 288-36-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; ALVARO, Giuseppe; AMANTINI, David; CASTIGLIONI, Emiliano; DI FABIO, Romano; PAVONE, Francesca; WO2010/63662; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 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. Formula: C2H3N3

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).

Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law. In my other articles, you can also check out more blogs about 288-36-8, and we look forward to future research findings.

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

Electric Literature of 288-36-8, New Advances in Chemical Research in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 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, below Introduce a new synthetic route.

To a solution of 1 ,2,3-trazole (10 g, 145 mmol) in 150 ml of THF were added potassium carbonate (40 g, 290 mmol) and MeI (13.58 ml, 217 mmol). The resulting reaction mixture was stirred at rt for 3hr. The reaction mixture was filtered and the filtrate was concentrated to afford the title compound (9.2 g, 78%). 1 H NMR (400 MHz, CDCI3) deltappm 7.71 (s, 1 H), 7.55 (s, 1 H), 4.14 (s, 3H).

This is the end of this tutorial post, and I hope it has helped your research about 288-36-8!

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/98104; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 288-36-8, New Advances in Chemical Research in 2021.Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media, 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, below Introduce a new synthetic route.

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 result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.I hope my blog about 1H-1,2,3-Triazole is helpful to your research.

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

Research speed reading in 2021. In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 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. Safety of 1H-1,2,3-Triazole

The 2 H – 1, 2, 3 – triazole (3.45 g, 50 mmol), 2 – iodo -5 – methyl benzoic acid (5.24 g, 20 mmol), cesium carbonate (11.72 g, 36 mmol), trans – N, N’ – dimethyl – 1, 2 – diaminocyclohexane (0.51 g, 3.6 mmol), cuprous iodide (0.38 g, 2 mmol) and N, N – dimethyl formamide (30 ml) are added to the 100 ml round bottom flask in a single port, under the protection of nitrogen reaction solution gradually raising the temperature to 100 C reaction 4 hours. Stopping the reaction, cooling, liquid water (60 ml) diluted with water and ethyl acetate (200 ml × 2) extraction. The water layer is acidified to pH concentrated hydrochloric acid for 1 – 2, then adding ethyl acetate (200 ml × 2) extraction, the resulting organic layer dried with anhydrous sodium sulfate, filtered, filtrate turns on lathe does after separation and purification by column chromatography (dichloromethane/methanol (v/v)=50/1) to obtain the title compound (yellow solid, 2.76 g, 68%).

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 1H-1,2,3-Triazole, in my other articles.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Zhang Yingjun; Xue Yaping; Lao Jinhua; Nie Biao; Xu Juan; (35 pag.)CN107759620; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 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

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 at 75 for 96 h. The reaction was diluted with water, washed with ether, and acidified with conc. HCl. The acidic aqueous solution was extracted 3x with EtOAc and the combined organic fractions were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by silica gel column chromatography [0-70 (1acetic acid in EtOAc) in hexanes] , providing the title compound as a solid. LRMS m/z (M+H) 196.2 found, 196.1 required.

The catalyzed pathway has a lower Ea, but the net change in energy that results from the reaction is not affected by the presence of a catalyst. In my other articles, you can also check out more blogs about 288-36-8

Reference:
Patent; MERCK SHARP & DOHME CORP.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; (59 pag.)WO2016/101118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics