Category: 288-36-8

Application of 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.

1, 2, 3-Triazole (3.45 g, 50 mmol) , 2-iodo-5-methylbenzoic acid (5.24 g, 20 mmol) , cesium carbonate (11.72 g, 36 mmol) , trans-N, N’-dimethyl-1, 2-cyclohexanediamine (0.51 g, 3.60 mmol) , cuprous iodide (0.38 g, 2 mmol) and N, N-dimethylformamide (30 mL) were added sequentially to a 100 mL of single-necked round-bottomed flask under nitrogen, and the mixture was warmed gradually to 100 and reacted for 4 h. The reaction mixture was cooled, diluted with water, and extracted with ethyl acetate (200 mL x 2) . The aqueous layer was acidified to pH 12 with concentrated hydrochloric acid, and the resulting mixture was extracted with ethyl acetate (200 mL x 2) . The combined organic layers were dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel eluted with (dichloromethane/methanol (v/v) 50/1) to give the title compound (as a yellow solid, 2.76 g, 68) .[MS (ESI, neg. ion) m/z: 202.1 [M-H]- and1H NMR (CD3OD, 600 MHz) delta (ppm) : 7.88 (s, 2H) , 7.66 (d, 1H) , 7.59 (d, J 8.2 Hz, 1H) , 7.507.48 (dd, J 8.1 Hz, 1.1 Hz, 1H) , 2.45 (s, 3H) .13C NMR (CD3OD, 151 MHz) delta (ppm) : 169.8, 140.7, 137.5, 136.7, 133.5, 131.5, 129.3, 126.0, 21.0.

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; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; JIN, Chuanfei; GAO, Jinheng; ZHANG, Ji; (107 pag.)WO2017/12502; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 288-36-8, 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.

Intermediate A 2-(2H-l .2.3-Triazol-2-yl)benzoyl acid A solution of 2-iodobenzoic acid (3.0 g, 12.09 mmol) in DMF (1.0 mL) was treated with 1,2,3-triazole (1.5 g, 21.7 mmol), copper(I) iodide (0.25 g, 1.2 mmol), Cs2C03 (7.08 g, 21.7 mmol), and fras-N,N’-dimethylcyclohexane-l ,2-diamine (0.31 g, 2.17 mmol). The mixture was heated at 120 C for 12h. The reaction was cooled to rt, diluted with EtOAc, and filtered through Celite. The residue was purified by gradient elution on Si02 (0 to 10% MeOH in DCM with 0.1% AcOH) to give the title compound.1HNMR (500 MHz, DMSO-d6) delta 13.05 (br s, 1H), 8.12 (s, 2H), 7.81-7.52 (m, 4H) ppm. LRMS m/z (M+H) 190.2 found, 190.2.

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; MERCK SHARP & DOHME CORP.; KIM, Ronald; KUDUK, Scott, D.; LIVERTON, Nigel; ZHUO, Gang; (116 pag.)WO2016/100161; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route 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.

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 colourless, turbid liquid. After filtration over Celite 1-But-3-ynyl-1H-[1,2,3]triazole was obtained as a colourless liquid (29.8 g, 40%). The content according to GC/FID was >98%. 1H-NMR (CDCl) 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).

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; Friess, Thomas; Reiff, Ulrike; Rueth, Matthias; Voss, Edgar; US2006/63812; (2006); A1;,
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 288-36-8 as follows. Product Details of 288-36-8

A mixture of 2,3-dichloro-5-nitropyridine (50 g, 259.08 mmol), 1H-1,2,3-triazole (19.683 g, 284.99 mmol), potassium carbonate (46.549 g, 336.81 mmol) and CH3CN (200 mL) was heated to 40 C. and stirred overnight. Ethyl acetate (500 mL) was added. The mixture was washed with water (500 mL*2) and brine (500 mL), dried over anhydrous Na2SO4, filtered, and concentrated to dryness under reduced pressure. The residue was triturated with DCM (100 mL), filtered, and the solid was collected to afford compound INT2A (40 g, 68%) as an off-white solid. LC-MS: (ES, m/z): [M+1]+ 225.9. 1H NMR (400 MHz, DMSO-d6) delta ppm 9.40 (d, J=2.0 Hz, 1H), 9.15 (d, J=2.0 Hz, 1H), 8.33 (s, 2H).

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; Lu, Tianbao; Connolly, Peter J.; Cummings, Maxwell David; Barbay, Joseph Kent; Kreutter, Kevin D.; Wu, Tongfei; Diels, Gaston Stanislas Marcella; Thuring, Jan Willem; Philippar, Ulrike; Edwards, James Patrick; Shen, Fang; (202 pag.)US2019/381019; (2019); 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., Quality Control of 1H-1,2,3-Triazole

To a stirred solution of 1,2, 3-triazole (2.0 g, 28.9 mmol) in THF (10 mL) was added NaH (l.065g, 43.1 mmol) portion wise at 0 C under inert atmosphere. After being stirred for 45 min at 0C, 2-(trimethylsilyl)ethoxymethyl-Cl (SEM-C1; 7.6 mL, 43.1 mmol) was added to the reaction mixture. After completion of addition the reaction mixture was allowed to warm to RT and stirred for 12 h. The reaction mixture was quenched with water and extracted with ethyl acetate (2 x 100 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure to give crude compound. The crude material was purified by column chromatography eluting with 10% EtO Ac/hexane to afford N-2-(trimethylsilyl)ethoxymethyl- 1,2, 3-triazole (3.5 g, 17.5 mmol, 61%) as a liquid. Mass: m/z 200 [M++l].

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; INNOCRIN PHARMACEUTICALS, INC.; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; EISNER, Joel; WAHL, Daniel; SPEERS, Corey; (111 pag.)WO2020/77197; (2020); A1;,
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. Computed Properties of C2H3N3

To a mixture of the product from step 2 (7.9 g, 38 mmol), Cs2CO3 (24.8 g,76 mmoi) and Ciii (2.88 g, 7.6 mmoi) in DMF (200 mL) were added 2H-[i,2,3]triazoie (5.24 g,76 mmoi) andN,N-.dimethyi-cyciohexanei,2diamine (0.9 g, 6.5 mmol) and the mixture was slirred at 110C overnight. The cooling mixture was adjusted to pi-ii2 with IM sodium hydroxide and extracted with EtOAc (50 rnL x 3). The aqueous layer was adjusted to pH 4 with 1M HC1 and extracted with EtOAc (50 mLx4). The extracts was dried over NaSO4, filtered, the filtrate concentrated in vacuo and the residue purified by chromatography on silica (Petroleum ether : EtOAc =10:1) toprovide the title compound (4.1 g). LRMS rnlz (M+H) 196,0 found, 196,0 required.

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; LIVERTON, Nigel; KUDUK, Scott D.; BESHORE, Doug C.; MENG, Na; LUO, Yunfu; (127 pag.)WO2016/101119; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. name: 1H-1,2,3-Triazole

Bromine (2.2 mL, 43.4 mmol) was added cautiously to a solution of 1H-1,2,3- triazole (2 g, 29.0 mmol) in water (10 mL) at 40C. The resulting mixture was stirred for 2 hrs at 40C, then allowed to cool and stood overnight at room temperature. The precipitate was isolated by filtration, washed with water (2×10 mL), and dried in the vacuum oven to give 4,5- dibromo-lH-l,2,3-triazole as a light brown solid. (M+H 225.6; LCMS method 2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 288-36-8, its application will become more common.

Reference:
Patent; IRM LLC; NOVARTIS AG; TELLEW, John Edward; WANG, Xia; WAN, Yongqin; XIE, Yun Feng; PAN, Shifeng; JIANG, Jiqing; XIE, Yongping; HUNT, Thomas Anthony; EDWARDS, Lee; BEATTIE, David; HEALY, Mark Patrick; WEST, Ryan; LISTER, Andrew Stuart; WO2012/138648; (2012); 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., Quality Control of 1H-1,2,3-Triazole

In a round-bottomed flask equipped with an overhead magnetic stirrer, reflux condenser, and nitrogen inlet were added 5-chloro-2-iodobenzoic acid (1 .15 g, 4.07 mmol), copper iodide (0.04 g, 0.2 mmol), and CS2CO3 (2.65 g, 8.14 mmol). To these solids were added dioxane (6 mL), water (0.05 mL), then 1 H-1 ,2,3-triazole (0.47 mL, 8.14 mmol), and finally trans-1 ,2-dimethylcyclohexane-1 ,2-diamine (0.3 mL, 0.81 mmol). The mixture was then warmed to 100 C for 4 hrs. Then the mixture was cooled and then MTBE and of water were added. After vigorous mixing, the layers were separated and the bottom aqueous layer was acidified to pH 2 with 6N HCI. The aqueous was then extracted twice with EtOAc. The combined organic layers were dried, filtered, and concentrated. The oil was stirred overnight in EtOAc (8 mL) and the resulting precipitate was removed by filtration affording a first crop of wanted product(100 mg). The mother-liquors were concentrated and purified by FC on S1O2 column (eluting from DCM to DCM : MeOH: 90: 10) to afford a second batch of the desired product that was mixed with the former to afford 5-chloro-2-(2H-1 ,2,3-triazol-2- yl)benzoic acid (p120, 620 mg, y=68%). MS (mlz): 223.9 [MH]+

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; CHRONOS THERAPEUTICS LIMITED; MICHELI, Fabrizio; BERTANI, Barbara; GIBSON, Karl Richard; DI FABIO, Romano; RAVEGLIA, Luca; ZANALETTI, Riccardo; CREMONESI, Susanna; POZZAN, Alfonso; SEMERARO, Teresa; TARSI, Luca; LUKER, Timothy Jon; (275 pag.)WO2019/43407; (2019); 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., Safety of 1H-1,2,3-Triazole

The iodide 19 (6.04 kg, 23.0 mol), THF (45 L) and DMF (9.0 L) were charged to a vessel. Copper iodide (218 g, 1.15 mol) and potassium carbonate (7.94 kg, 57.4 mol) were added and the mixture heated to an internal temperature of 40 C. 1 ,2,3-Triazole (3.16 kg, 46., 0 mol) was added as a solution in THF (6.0 L) over half an hour (no exotherm) and heating continued to 65 C (again no exotherm observed) and the reaction monitored by HPLC. Once complete Nu,Nu-dimethylethylenedi amine (244 mL, 2.30 mol) was added and mixture cooled to RT. Aqueous 3.6 M HC1 (36 L) was added (exotherm) and the mixture extracted twice with ethyl acetate (2 x 30 L). The combined organics were washed with LiCl solution (2 x 20 L). The acid solution assayed for 3.79 kg of 5 (81%) and 4.64 kg of 5 and 20 combined (99%). A solution of acids 5 and 20 (approx. 4.64 kg, 22.9 mol) in THF and EtOAc (approx. 1 10 L) was concentrated to low volume. THF (90 L) was added and the solvent composition checked by 1H NMR to ensure most ethyl acetate had been removed. Sodium tert-butoxide (2.42 kg, 25.2 mol) was added slowly as a solid over 1-2 h (slight exotherm), allowing the sodium salt to form and stirred overnight at RT. The liquors showed a 45:55 ratio of product 5: starting material 19 and the solid was collected by filtration, washed with THF (2 x 20 L) and dried in a vacuum oven (T = 40 C) for 15 h to afford 4.22 kg of crude sodium salt. The crude sodium salt (4,22 kg, 14.9 mol) was charged to a 50 L vessel and 3.6 M HC1 (21.2 L) was added with cooling. The slurry was then stirred at room temperature for 16 h and the off-white solid isolated by filtration. The cake was washed with water (11 L) and iP Ac/Heptane (2 chi 5L), then dried in a vacuum oven (T = 35 C) for 15 h to give 3.10 kg of crude acid 5 (97.9 LCAP, 92 wt%, corrected weight 2.85 kg, 61% yield from 19). The acid 5 (2.85 kg corrected, 14.0 mol) was charged to a 50 L vessel and EtOAc (28 L) and dilute 0.22 M HC1 (14 L) were added and the mixture stirred until two clear phases resulted. The aqueous layer was removed and the organic layer filtered to remove any particulate matter. The ethyl acetate was reduced to about 8 L and then heptane (15.6 L) was added over 1 h and the liquors sampled to check for appropriate losses. The solid was isolated by filtration, washed with heptane :ethyl acetate (3: 1, 4 L) and dried on the filter under nitrogen to give 2.81 kg of acid 5. m.p. 167.5 C. NMR (400 MHz, d6-DMSO): delta 12.09 (br s, 1H)S 8.04 (s, 1H), 7.62 (d, 1H, J = 8.4 Hz), 7.58 (d, 1H, J – 1.2 Hz), 7.49 (dd, 1H, J = 8.4, 1.2 Hz), 2.41 (s, 3H). 13C NMR (100.6 MHz, d6-DMSO): delta 168.0, 139.2, 136.4, 135.8, 132.5, 130.3, 128.7, 124.8, 20.9. HRMS (ESI): m/z [M+ + H] calcd for C]0H9N3O2: 204.0773; found: 204.0781

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.; MERCK SHARP & DOHME LIMITED; BAXTER, Carl, A.; CLEATOR, Edward; KRSKA, Shane, W.; SHEEN, Faye; STEWART, Gavin; STROTMAN, Neil; WALLACE, Debra, J.; WRIGHT, Timothy; WO2012/148553; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 288-36-8, 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.

To a solution of 1H-1,2,3-triazole (0.524 mL, 9.05 mmol) in water (5 mL) at 50 C was added bromine (0.625 mL, 12.13 mmol). The reaction was stirred at 50 C for 90 minutes, whereupon the precipitated product was filtered off. This material was air-dried on the filter. Another aliquot of bromine (0.625 mL, 12.13 mmol) was added to the mother liquor, which was stirred at room temperature overnight. After stirring overnight, collected the solid product by filtration. Filtered off a total of 4,5-dibromo-1H-1,2,3-triazole (1.83 g, 7.91 mmol, 87 % yield) as a white solid. Carried on as-is to alkylation.

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; BRISTOL-MYERS SQUIBB COMPANY; SPERGEL, Steven H.; PITTS, William J.; MERTZMAN, Michael E.; MOSLIN, Ryan M.; SHERWOOD, Trevor C.; GILMORE, John L.; DYCKMAN, Alaric J.; (0 pag.)WO2020/92196; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics