Triazoles

6523-49-5, The chemical industry reduces the impact on the environment during synthesis 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, I believe this compound will play a more active role in future production and life.

To a stirred solution of l-(4-aminophenyl)-l,2,4-triazole (1.0 g, 6.25 mmol) in MeOH (10 mL) and water (10 mL) was added CaCO3 (1.2 g, 12.0 mmol), followed by a solution of iodine monochloride (1.2 g, 7.38 mmol) in MeOH (10 mL). The reaction mixture was stirred at r.t. for 1.5 h, and then partitioned between EtOAc (100 mL) and aqueous sat. Na2S2O3 (100 mL). The organic fraction was separated, washed with aqueous sat. Na2S2O3 (100 mL), then water (100 mL), brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification by column chromatography (SiO2, 0- 100% EtOAc/hexanes) gave the title compound (1.2 g, 67%). LCMS (ES+) 286.9 (M+eta)+, RT 2.78 minutes {Method 4).

The chemical industry reduces the impact on the environment during synthesis 6523-49-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; UCB PHARMA S.A.; WO2008/47109; (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. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., 7411-23-6

In a 250 mL round bottomed flask sodium hydride (60% dispersion in mineral oil) (264 mg, 6.61 mmol) was added to a colorless solution of 3,5-dibromo-lH-l,2,4-triazole (lnt-1, 1 g, 4.41 mmol) in DMF (22 ml). The resulting suspension was stirred at room temp during 30 min and 1,1,1,3,3,3-hexadeuterio-2-bromopropane (683 mg, 5.29 mmol) was added and the reaction was stirred at 40C over night.The reaction mixture was poured into 50 mL H20 and extracted with EtOAc (3 x 50 mL). The organic layers were washed with sat NaCl (3 x 50 mL), dried over MgS04 and concentrated in vacuo. The title compound was isolated as a colourless liquid (644 mg, 2.34 mmol, 53.1 % yield). MS (ES+) m/z 275.9 [(M+H)+].

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-88-0, 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. 288-88-0, name is 1H-1,2,4-Triazole, This compound has unique chemical properties. The synthetic route is as follows.

Example 8; In DMSO (26.4ml), (2R, 3R)-3-(2,4-difluorophenyl)-3,4-epoxy-2-butanol (20.0g, 0.1 mol) and 1,2,4-triazole (10.4g, 0.15 mol) were dissolved and heated to about 60C with stirring. 20% aqueous sodium hydroxide solution (6.0g, 0.03 mol) was dropped thereto over about 15 minutes and further stirred for 5 hours at the same temperature for the reaction. After the reaction, the mixture was cooled, diluted with water (40ml) and neutralized (pH 6-7) with 35% hydrochloric acid. Ethyl acetate (100ml) was added, stirred and subjected to phase separation. The water layer was extracted with ethyl acetate (100ml) three times. A part of the ethyl acetate was taken and concentrated, and then NMR was measured to confirm the sample is (2R, 3R)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol. 1H-NMR (CDCl3, delta ppm) 0.98 (3H, d, J=6Hz), 2.62 (1H, d, J=9Hz), 4.31-4.34 (1H, m), 4.79, 4.80 (each 1H, d, J=14Hz), 4.82 (1H, s), 6.72-6.79 (2H, m), 7.38-7.45 (1H, m), 7.83, 7.85 (each 1H, s) The ethyl acetate layers were combined and then distilled off under a reduced pressure. Subsequently, toluene (50ml) and triethylamine (65.8g, 0.65 mol) were added thereto and cooled to about 5C and stirred. Methanesulfonyl chloride (17.2g, 0.15 mol) was dropped thereto over about one hour and stirred for 30 minutes at the same temperature for the reaction. After the reaction, water (50 ml) was poured into and stirred, and then water layer was separated and extracted with toluene (100ml) three times. The combined toluene layers were washed with water and the solvent was distilled off under a reduced pressure. The concentrated residue was subjected to recrystallization from a mixed solvent of toluene/heptane (20/80; v/v, 400ml) to give (2R, 3S)-2-(2,4-difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane. (11.6g, yield 46.2%, optical purity (HPLC condition-1) 100%e.e., mp 89C)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP1818332; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-88-0, 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. 288-88-0, name is 1H-1,2,4-Triazole, A new synthetic method of this compound is introduced below.

General procedure: A mixture of 4-fluorobenzaldehyde (8.85 mL, 0.1 mol), the corresponding phenol, thiophenol or amine (0.1 mol), and a catalytic quantity of potassium carbonate (K2CO3) was refluxed in DMF (20 mL) for 36 h. After completion of the reaction, the mixture was poured into ice-water (50 mL), and the precipitated product was filtered, washed with deionised water, dried, and recrystallized from EtOH.

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:
Article; Can, Nafiz Oencue; Can, Nafiz nc; Osmaniye, Derya; Levent, Serkan; Sa Sa?lik, Beguem Nurpelin; Inci, Beril; Ilgin, Sinem; Oezkay, Yusuf; Kaplancikli, Zafer Asim; Molecules; vol. 22; 8; (2017);,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common compound: 217448-86-7, name is Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate, 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. 217448-86-7

In a 250 ml round bottom flask, 2,6-difluorobenzylbromide (0.024 mol, 5 g), sodium azide (0.026 mol, 1.72 g) and water (50 ml) were added. The reaction mixture was heated to 700C to 750C for 30 hours and formation of the azide intermediate was monitored by thin layer chromatography (TLC). After the completion of reaction, the reaction contents were cooled to room temperature and then to this methyl propiolate (0.024 mol, 2.1 ml) was added dropwise, maintaining the contents at room temperature. On complete addition, the mixture was again heated at 600C to 650C for 4 to 5 hours. After the reaction was completed, the contents were cooled to room temperature and to this 25% aqueous ammonia (40 ml) solution was added dropwise. The reaction contents were heated to 700C to 750C for 4 to 5 hours and then gradually cooled to room temperature. The solid obtained was filtered and washed with water. The product was dried under vacuum at 700C – 750C to give 3.0 g of rufinamide.

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, 217448-86-7, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CIPLA LIMITED; KANKAN, Rajendra, Narayanrao; RAO, Dharmaraj, Ramachandra; BIRARI, Dilip, Ramdas; CURTIS, Philip, Anthony; WO2010/43849; (2010); 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: 20 mg of gamma-Fe2O3Ph-PMO-NaHSO4 was added to a roundbottomflask containing an aromatic aldehyde (1 mmol), 3-amino-1,2,4-triazole 2 (1.0 mmol), b-diketones (dimedone 3, 1,3-cyclohexadione 4 or ethyl acetoacetate 5) (1.0 mmol) and stirredunder solvent-free conditions at 100 C in certain times. Meanwhile,the progress of the reactionwas indicated by TLC (n-hexane:ethyl acetate; 7:3). With completing the reaction, 3ml ethanol waspoured and the magnetic nanocomposite was separated in thepresence of a magnetic stirring bar; the reaction mixture becameclear. The crude product was recrystallized from ethanol to give thepure product. The pure products were characterized by conventionalspectroscopic methods. Physical and spectral data for theselected compounds are represented below.

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; Haghighat, Mahdieh; Shirini, Farhad; Golshekan, Mostafa; Journal of Molecular Structure; vol. 1171; (2018); p. 168 – 178;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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.

To a so?ution of 2-choro-5-nitro-3-(trifluoromethy)pyridine (1 .0 g, 4.41 mmo) and K2CQ3 (1.22 g, 883 mmo) in THF (5 m) was added 2H-l ,2,3-triazoe (0.31 m, 5.30 mmo). The reaction mixture was stirred for lh at RT. Water was added and the mixture was extracted with AcOEt. The organic ayer was washed with brine, dried over Na2SO4, fHtered and concentrated under vacuum. The residue was purified by flash co?umn chromatography on sHica ge (cycohexane/AcOEt: 100/0 to 50/50) to afford 5-nitro-2- (2H-1 ,2,3-triazo-2-y 3-(trifluoromethy)pyridine. Miz = 260 [M+H]+, Rt = 0.88 mm (UPLC Method 81), 1H NMR (400 MHz, DMSO-d6) O ppm: 9.69 (d, IH), 9.17 (d, IH), 8,37 (s, 2H).

The synthetic route of 1H-1,2,3-Triazole has been constantly updated, and we look forward to future research findings.

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,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 iodide 19 (6.04 kg, 23.0 mol), THF (45 E) and DMF (9.0 E) 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 of40 C. 1,2,3-Triazole (3.16 kg, 46.0 mol) was added as asolution in THF (6.0 E) over half an hour (no exotherm) andheating continued to 65 C. (again no exotherm observed) and the reaction monitored by HPEC. Once complete N,Ndimethylethylenediamine (244 mE, 2.30 mol) was addedand mixture cooled to RT. Aqueous 3.6 M HC1 (36 E) wasadded (exotherm) and the mixture extracted twice with ethylacetate (2×30 E). The combined organics were washed with EiC1 solution (2×20 E). 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. 110 E) was concentrated to lowvolume. THF (90 E) was added and the solvent composition checked by ?H 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:starting material and the solid was collected by filtration, washed with THF (2×20 E) 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 E vessel and 3.6 M HC1 (21.2 E) was added with cooling. The slurry was thenstirred at room temperature for 16 h and the off-white solidisolated by filtration. The cake was washed with water (11E) and iPAc/Heptane (2×5 E), then dried in a vacuum oven(T=35 C.) for 15 h to give 3.10 kg of crude acid 5 (97.9ECAP, 92 wt %, corrected weight 2.85 kg, 61% yield from19). The acid 5 (2.85 kg corrected, 14.0 mol) was chargedto a 50 E vessel and EtOAc (28 E) and dilute 0.22 M HC1 (14 E) 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. Theethyl acetate was reduced to about 8 E and then heptane (15.6 E) 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 E) and dried on the filter under nitrogen to give 2.81 kg of acid 5.m.p. 167.5 C. ?H NMR (400 MHz, d5-DMSO): oe 12.09 (brs, 1H), 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). ?3C NMR (100.6 MHz, d5-DMSO): oe 168.0, 139.2, 136.4, 135.8, 132.5, 130.3, 128.7, 124.8, 20.9. HRMS (ESI): mlz [M+H] calcd for C,0H9N302: 204.0773; found: 204.0781.

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; MERCK SHARP & DOHME CORP.; Fleitz, Fred; Mangion, Ian; Yin, Jingjun; (11 pag.)US9441254; (2016); B2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

16681-65-5, 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 16681-65-5 as follows.

Intermediate 77: step a N-methoxy-N-1-dimethyl-1H-1,2,3-triazole-5-carboxamide A solution of 1 -methyl- 1H- 1 ,2,3-triazole (12.9 g, 155 mmol) in THF (260 mL) was cooled to – 45 C. Maintaining a temperature of < -35 C, -BuLi (62.5 mL, 2,5 M in hexanes, 155 mmol) was added over 10 minutes. The reaction mixture was stirred for 30 minutes with cooling to -45 C and then treated with a sub-surface stream of CQ2(g)for a period of 2 hours. After flushing the -35 C slurry with Ng)for 5 minutes, thionyi chloride (11 ,8 mL, 163 mmol) was added. The mixture was allowed to warm to room temperature with stirring over 1.25 hours. Then, N,0-dimethyihydroxylamine hydrochloride (18.14 g, 186 mmol) and AyV-diisopropy ethylamine (68.3 mL, 396 mmol) were added and the resulting mixture stirred for 15 hours. Aqueous sodium carbonate (500 mL, 10 wt%) was then added, and the layers were mixed and separated. The aqueous layer was washed with dichloro methane (250 mL and then 125 mL), and the combined organic layers were dried over MgS04, filtered, and concentrated. The residue was taken up in ethyl acetate (225 mL), treated with MgS04, and filtered through a pad of silica gel (115 g). The silica gel pad was washed with additional ethyl acetate (800 mL). The eluent was concentrated to provide the title compound as a yellow solid According to the analysis of related databases, 1-Methyl-1H-1,2,3-triazole, the application of this compound in the production field has become more and more popular. 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; CUMMINGS, Maxwell D.; JONES, William Moore; GOLDBERG, Steven; WO2015/57205; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 15294-81-2, name is 4,5-Dibromo-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 15294-81-2, 15294-81-2

Example 160: Preparation of 4,5-dibromo-l-methyl-lH-[1.2.31triazole and 4,5-dibromo- 2-methyl-2H-r 1 ,231triazole(A) (B)To a solution of 4,5-dibromo- IH-[1, 2,3]triazole (2.26 g, 10 mmol) (Example 159) and triethyl amine (1.5 ml, 10 mmol) in dichloromethane (50 ml), was added methyl iodide (625 mul, 10 mmol). The reaction mixture was stirred at room temperature for 24 hours. More triethyl amine (0.75 ml, 5 mmol) and more methyl iodide (312 mul, 5 mmol) were added and the mixture was stirred for 3 hours. The reaction mixture was quenched with aqueous ammonium chloride (saturated, 15 ml). The organic extract was dried over magnesium sulfate and concentrated and the residue was purified by column chromatography on silica gel (eluent 10-30% ethyl acetate in hexane) to give 4,5-dibromo-2- methyl-2H-[l ,2,3]triazole (isomer B) (625 mg, 26% yield) and 4,5-dibromo- 1-methyl- IH-[1, 2,3]triazole (isomer A) (825 mg, 34% yield). Isomer A 1H-NMR (400 MHz, CDCl3): 4.09 (s, 3H, Me) ppm. Isomer B 1H-NMR (400 MHz, CDCl3): 4.18 (s, 3H, Me) ppm.

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, 4,5-Dibromo-1H-1,2,3-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA LIMITED; WO2007/71900; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics