Category: 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., 288-36-8

Sodium hydride (5.3 g, 220.85 mmol, 1.50 equiv) was added in portions to a stirred mixture of1H-1,2,3-triazole (10 g, 144.79 mmol, 1.00 equiv) in THF (500 mL) at 0 C under nitrogen. After1 hour 2-(trimethylsilyl)ethoxymethyl chloride (36 g, 235.76 mmol, 1.60 equiv) was added and theresulting solution was stirred for 12 h at room temperature. The reaction was quenched by water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:10). This resulted in 10 g (28%) of the title compound as yellow oil. LC-MS (ES, mlz): 200 [M+H].

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; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; BURCH, Jason; CASTANEDO, Georgette; FENG, Jianwen A.; HU, Baihua; STABEN, Steven; WU, Guosheng; YUEN, Po-wai; WO2015/25025; (2015); 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.

Intermediate H 4-Fluoro-2-(2H-l,2,3-triazol-2-yl)benzoic acid Intermediate H 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 NN’- dimethylcyclohexane-l,2-diamine (3.7 mL,23.3 mmol) and lH-l,2,3-triazole (18.92 g, 274 mmol). The resulting mixture was stirred at 110 C overnight, cooled, concentrated in vacuo and diluted with water (150 mL). The aqueous mixture was extracted with EtOAc (300 mL x 3). The aqueous layer was acidified with 2Nu HC1 and extracted with EtOAc (300 mL x 4). The combined organic layers were washed with brine (150 mL x 3), dried over Na2SC>4, filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel (petroleum ether : EtOAc = 100: 1 ~ 5 : 1) to provide the title compound. 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.; 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

288-36-8, Adding a certain compound to certain chemical reactions, such as: 288-36-8, name is 1H-1,2,3-Triazole, belongs to Triazoles compound, 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.

lH-Triazole (760 mg, 11 mmol) was added to a suspension of 2,3-dichloro-5-nitro-pyridine (965 mg, 5 mmol) and anhydrous potassium carbonate (1.03 g, 7.5 mmol) in THF (50 mL), and the mixture was stirred overnight at room temperature. The mixture was diluted with EtOAc (100 mL), washed with water and brine, and the organic phase was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica chromatography (hexane: EtOAc= 5: 1 to 1: 1) to give the title compound (505 mg, 44%). 1H NMR (400 MHz, DMSO-iM): delta 9.39 (d, 1H), 9.15 (d, 1H), 8.34 (s, 2H).

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; CORNELL UNIVERSITY; DANA-FARBER CANCER INSTITUTE, INC.; CHILDREN’S MEDICAL CENTER CORPORATION; MELNICK, Ari, M.; GABAS, Lorena, Fontan; US, Ilkay; CASALENA, Gabriella; GRAY, Nathanael, S.; SCOTT, David, A.; HATCHER, John; DU, Guangyan; WU, Hao; QIAO, Qi; (157 pag.)WO2018/85247; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, The chemical industry reduces the impact on the environment during synthesis 288-36-8, name is 1H-1,2,3-Triazole, I believe this compound will play a more active role in future production and life.

In the reactor,Add 250mL of acetone,Stirring,26.2 g of 2-iodo-5-methylbenzoic acid,Then 34.5 g of potassium carbonate was added,0.38 g copper iodide (Cul),1,2,3-triazole 7.6g.External temperature was raised to 70 C,During the heating process, a large amount of gas is generated,The reaction was refluxed for 5 hours.Then the reaction mixture was distilled under reduced pressure, the reaction system is more viscous, add 30mL of water, continue to reduce the steam distillation to no acetone (no acetone gas phase). 300mL of water was added to the residue after distillation, and 6mo 1 / L hydrochloric acid was added dropwise at room temperature to adjust the pH of the system to 1-2, resulting in a khaki-colored suspension liquid. Stirred for 15 minutes, filtered, washed with water three times,Each 50mL. The resulting solid was dried at 70 C in vacuo to dryness,Have pale green solid 19.45g,For crude compound (1-1), the purity was 95.20%.With stirring, 7.5 kg of acetone, 0.94 kg of crude compound (1-1) and 0.194 kg of sodium hydroxide were added to the reaction kettle. Stirred at 20 C-30 C for 14 hours. Centrifugation, The filter cake was washed 3 times with acetone, each time 3kg. The resulting solid was transferred to the reaction kettle , 5.65 kg of water was added, 0.14 kg of diatomaceous earth was added and stirred for 1 hour. Filtration, the filtrate was transferred to the reaction kettle, hydrochloric acid was added dropwise to adjust the pH to 1-2, a large amount of white solid formed and stirred for 1 hour. Filtered, the filter cake was washed with water three times, each time 3kg. The resulting solid was dried at 60 C in vacuo to dryness, 0.71 kg white solid, represents Compound (I-1), purity 99.97%, Isomeric compound (1-2) less than 0.1%.

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; He Bifei; Fan Yuping; (6 pag.)CN104649983; (2018); B;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, A common compound: 288-36-8, name is 1H-1,2,3-Triazole, 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.

To a soution of 23-dichoro-5-nitropyridine (lOg, 5.18 mmo) and K2003 (1.43 g, 10.4 mmo) in THF (5 m) was added 2H-1,2.3-triazoe (0.360 m, 6.22 mrnoD. The reaction mixture was stirred for overnight at RT. Since the reaction was uncompete, additiona 2H-1,2,3-triazoe (0.300 mL 5.18 mmo) was added and reaction mixture was stirred over2 days at RT. Water was added and the mixture was extracted with AcOEt. The organic ayer was washed with brine, dried over Na2SO4, fi[tered and concentrated under vacuum. The residue taken-up in DCM, the soHd was fHtered off and the fi[trate was evaporated. The residue was purified by flash cournn chromatography on si?ica g& (cycohexane/AcOEt: 1/0 to 7/3) to afford 3-choro-5-nitro-2-(2H-1 2,3-triazo-2- y)pyridine. Rt = 0.75 mm (UPLC Method BI), 1H NMR (400 MHz, DMSO-d6) O ppm:939 (d, IH), 9.15 (d, IH), 833 (s, 2H).

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; NOVARTIS AG; PISSOT SOLDERMANN, Carole; QUANCARD, Jean; SCHLAPBACH, Achim; SIMIC, Oliver; TINTELNOT-BLOMLEY, Marina; ZOLLER, Thomas; (161 pag.)WO2015/181747; (2015); A1;,
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 3-chloro-4-fluoronitrobenzene (1.2 g, 6.836 mmol) and 2H-1,2,3-triazole (0.567 g, 8.203 mmol) in anhydrous DMA (5 mL) was added K2CO3 (1.89 g, 13.7 mmol). The reaction mixture was stirred at 55 C. overnight. The reaction was concentrated to give a crude oil. The crude product was purified by flash column chromatography over silica gel (petroleum ether/ethyl acetate from 100/0 to 20/80) to give compound 4d (1 g, 65.1%) as a yellow solid. 1H NMR (400 MHz, CDCl3) delta ppm 7.88-8.02 (m, 3H), 8.28 (dd, J=8.93, 2.54 Hz, 1H), 8.49 (d, J=2.21 Hz, 1H).

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; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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.

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-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 room temperature, 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 10% MeOH in DCM with 0.1% AcOH) to give the faster eluting 2-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid A-2, followed by the undesired regioisomer isomer, l-(2H-l,2,3-triazol-2-yl)-5-methylbenzoic acid. A solution of the acid (3.56 g, 17.52 mmol) in 150 mL of DCM was stirred and cooled to 00C. The solution was treated with oxalyl chloride (1.9 mL, 21.9 mmol) and DMF (68 muL, .878 mmol). The solution was slowly warmed to room temperature and stirred overnight. Solvent was concentrated and the resulting solid was azetroped with DCM and concentrated to provide A-4 as a yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 288-36-8, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SHARP & DOHME CORP.; COX, Christopher, D.; FLORES, Broc; SCHREIER, John, D.; WO2010/48016; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 288-36-8, name is 1H-1,2,3-Triazole, I believe this compound will play a more active role in future production and life. 288-36-8

A) to the reactor were added successively 1mol difluorophenyl chloride, 1.2mol triazole, 0.15molCuI, 1.5mol potassium carbonate and 0.8LDMF (N, N- dimethylformamide), heated to 80 stirred 10 hours, TLC (thin layer chromatography) to detect the reaction was complete; the filtrate was filtered, concentrated under reduced pressure recovery DMF, the residue is recrystallized from ethyl acetate-white solid, that is the first product in a yield of 73% ;

The chemical industry reduces the impact on the environment during synthesis 288-36-8. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Liu, Ke; (7 pag.)CN105777740; (2016); A;,
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. 288-36-8

Intermediate 3: 5-Methyl-2-(2H-l,2,3-triazol-2-yl)benzoic acid To the solution of 1,2,3-triazole (1.99 g, 28.93 mmol) in DMF (7.0 ml) at 0-10UC was added cesium carbonate (4.7 g, 14.45 mmol), N,N-dimethylethylenediamine (0.127 g, 1.45 mmol), copper(I) iodide (0.068 g, 0.36 mmol) and 2-iodo-5-methylbenzoic acid (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 (sodium sulphate) and concentrated in vacuo. The crude product was purified by column chromatography (0-3 % methanol in dichloromethane) to afford the title compound.1H NMR (DMSO-i/6) delta ppm 2.42 (s, 3 Eta), 7.49 – 7.52 (m, 1 Eta), 7.58 – 7.64 (m, 2 Eta), 8.05 (s, 2 H), 13.01 (s, 1 H)MS ES+: 204

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; TAKEDA CAMBRIDGE LIMITED; TAKEDA PHARMACEUTICAL COMPANY LIMITED; FIELDHOUSE, Charlotte; GLEN, Angela; ROBINSON, John Stephen; FUJIMOTO, Tatsuhiko; WO2015/55994; (2015); 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. 288-36-8

To a mixture ofthe product from step 2 (7.9 g, 38 mmol), cesium carbonate(24.830 g,76 mmol) and Cui (2.88 g, 7.6 mmol) in DMF (200 mL) were added 2H-[1,2,3]triazole (5.24g,76 mmol) and N,N’-dimethyl-cyclohexane-1,2-diamine (0.9 g, 6.5 mmol) and the mixture washeated to 110 C overnight. The cooled reaction mixture was adjusted to ~pH 12 with 1Msodium hydroxide and extracted with EtOAc (50 mL x 3). The aqueous layer was adjusted to~pH 4 with 1M HCl and extracted with EtOAc (50 mLx4). The extracts was dried over Na2S04,35 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.

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; MERCK SHARP & DOHME CORP.; BESHORE, Douglas C.; KUDUK, Scott D.; LIVERTON, Nigel; LUO, Yunfu; MENG, Na; YU, Tingting; WO2015/18029; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics