Triazoles

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. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C3H5N3

Example 43a: (4-chloro-2-methoxy-3-((6-(trifluoromethyl)pyridin-3-yl)methyl)quinolin-6-yl)(1,2-dimethyl-1H-imidazol-5-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol A solution of n-BuLi (2.5 M in hexanes, 1.25 mL, 3.12 mmol) was added dropwise by syringe to a solution of 1 -methyl- 1 H- 1 ,2,3-triazole (268 mg, 3.22 mmol) in dry THF (32 mL) in a dry ice- methanol bath. The suspension was stirred for 30 minutes, slowly allowing the reaction mixture to warm to -10 C, (4-Chloro-2-methoxy-3-((6-(trifluoromethyl)pyTidin-3-yl)methyl)quinoiin-6- yi)(l ,2-dimethyl-lH-imida.zol-5-yl)methanone (0.500 g, 1 ,05 mmol, Intermediate 45: step f) in dry THF (5 mL) was added to the mixture via syringe and the resulting mixture was allowed to warm to ambient temperature overnight. The reaction was quenched with water. Brine was added and the aqueous mixture was extracted with ethyl acetate. The combined organic layers were dried (Na2S04), filtered, and concentrated. The crude product was purified by flash column chromatography (silica gel, 0-8% MeOH-DCM) to provide the title compound.JH NMR (500MHz, CDC1 delta 8.69 (d, J = 1.7 Hz, 1H), 8.24 (d, J = 1.9 Hz, 1H), 8.22 (s, IH), 7.79 – 7.76 (m, 1H), 7.75 (d, J = 8.7 Hz, 1H), 7.57 (d, J = 8.1 Hz, 1H), 7.42 (dd, J = 8.7, 2.0 Hz, 1H), 6.97 (s, 1H), 5.95 (s, 1H), 4.30 (s, 2H), 4.08 (s, 3H), 3.88 (s, 3H), 3.33 (s, 3H), 2.12 (s, 3H); MS m/e 557.8 [M+H]+.Example 43a was purified by ehiral SFC (ChiralPak AD-H, 70:30 C02:mixture of MeOH/iPrOH (50:50 with 0.3% /PrNH2)) to provide two pure enantiomers. The first eluting enantiomer was Example 43b: 1H NMR (400 MHz, CDC13) delta 8.72 (d, J = 1 .7 Hz, 1H), 8.21 (d, J = 2.1 Hz, 1H), 7.78 (dd, J —— 8.1 , 1 .7 Hz, I I I). 7.74 (d, J —— 8.7 Hz, 1 H), 7.58 id, J = 7.9 Hz,I I I). 7.40 (dd, J —– 8.7, 2,2 Hz, i l l). 7.50 (s, I H), 6.04 (s, 1H), 4.34 (s, 2H), 4.08 (s, M i l 3.89 (s,3H), 3.36 (s, 3H), 2.24 (s, 3H); MS m/e 557.2 [MJ+. The second eluting enantiomer was Example 43c: H NMR (400 MHz, CDC13) delta 8.73 (d, J = 1.8 Hz, 5 H), 8.20 (d, J === 2.0 Hz, 1H), 7.80 – 7.73 (m, 2H), 7.58 (d, J = 8.0 Hz, 1 H), 7.40 (dd, J = 8.7, 2.1 Hz, 1H), 7.52 (s, IH), 6.06 (s, IH), 4.35 (s, 21 1). 4.08 (s, 3H), 3.90 (s, 3H), 3.37 (s, 3H), 2.26 (s, 3H); MS m/e 557.2 i VI i

The synthetic route of 16681-65-5 has been constantly updated, and we look forward to future research findings.

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

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. 61-82-5, name is 1H-1,2,4-Triazol-5-amine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C2H4N4

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

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.

2H-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, 3.6 mmol)Cuprous iodide (0.38 g, 2 mmol),N, N-dimethylformamide (30 mL) were successively added to a 100 mL single-necked round bottom flask,Under the protection of nitrogen gradually heated to 100 ,Reaction for 4 hours.Stop the reaction,cool down,Diluted with tap water and extracted with ethyl acetate (200 mL x 2).The aqueous layer was acidified with concentrated hydrochloric acid to pH = 1 to 2 and extracted with ethyl acetate (200 mL x 2)The combined organic layers were combined and dried over anhydrous sodium sulphate,filter,The filtrate was evaporated under reduced pressure and purified by column chromatography (dichloromethane / methanol (v / v) = 50 / 1) to afford the title compound (yellow solid, 2.76 g, 68%).

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

Reference:
Patent; Guangdong HEC Pharmaceutical Co., Ltd.; Jin, Chuanfei; Gao, Jinheng; Zhang, Yingjun; (39 pag.)CN106243052; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 342617-08-7, These common heterocyclic compound, 342617-08-7, name is 3-(3-Bromophenyl)-4H-1,2,4-triazole, 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.

Step 2: [3-(3-Bromophenyl)-1H-1,2,4-triazol-1-yl]methyl 2,2-dimethyipropanoate A slurry of 3-(3-bromophenyl)-1H-1,2,4-triazole (58.5 g; 261 mmol; Step 1 above), anhydrous K2CO3 (43.2 g; 313 mmol), and chloromethylpivalate (45 mL; 313 mmol) in dry MeCN (250 mL) was heated to 80 C. (Note 1) for 1 hour. The mixture was cooled, solid was collected by filtration and the filtrate was concentrated in vacuo. Residue from the filtaret was combined with the filtered solid and the whole was stirred with water approximately 20 minutes. Solid was collected by filtration, washed with water (*3) and recrystallized from MeOH/water, affording the title compound as a colorless solid. LC/MS (method E) tR 0.88 min, m/z 338, 340 (M+H, Br isotopes). The following were prepared from the appropriate benzamides by a procedure similar to Example IV-25.

The synthetic route of 342617-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IGNAR, DIANE MICHELE; US2010/113512; (2010); 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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, A new synthetic method of this compound is introduced below., Safety of 3,5-Diamino-1,2,4-triazole

Added to three neck fever bottle 126mmol stearic acid, 60mmol3,5-diamino -1, 2, 4-three nitrogen […] 21g glycol solvent, under the protection of argon gas, heating 80 ¡ãC after melting, by adding 3mmol potassium hydroxide, wherein stearic acid: 3,5-diamino -1, 2, 4-triazole: potassium hydroxide mole ratio is 2.1: 1 : 0.05, glycol as the above-mentioned reactant of the total weight of the 50percent. Continued heating to 150 ¡ãC, reaction 12h rear, with 1percent sodium carbonate water solution, in order to remove unreacted stearic acid and the solvent is ethylene glycol, drying to obtain yellow solid containing heterocyclic stearic acid amide-based intermediate A.

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; China Petroleum & Chemical Corporation; Yu, Jianye; Lu, Minhui; Yuan, Ping; Yuan, Yufeng; (9 pag.)CN105693640; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 956317-36-5, 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. 956317-36-5 name is 5-Methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, 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.

The amine DBT salt 16 (5,67 kg, 9.09 mol) was charged to a vessel and inerted. DCM (28 L) was added, followed by 4 N Sodium Hydroxide solution (prepared from 10 N NaOH [22,4 L] and water [36 L]), The slurry was then stirred at ambient temperature for 1 h until a solution was obtained. The layers were separated and the aqueous phase treated with sodium chloride solution (10.1 kg in 20 L water). DCM (5 L) was then added and the bi-phasic mixture stirred for 10 min before separating the layers. The combined organic layers were then concentrated under reduced pressure to a 10 L volume. The solution of the free amine was used directly in the next reaction. The triazole acid 5 (13.25 kg, 65.2 mol), DCM (88 L) and DMF (1.35 L, 17.4 mol) were charged to a vessel and the resulting suspension was cooled to 0 C. Oxalyl chloride (8.28 kg, 65,2 mol) was added portion wise keeping the internal temperature between 5 and 10 C (the anhydride formed above 10 C), then the reaction was aged for 30 min at thistemperature. HPLC analysis showed acid 5 remained; an additional charge of oxalyl chloride (160 g, 1.26 mol) was made, and the solution stirred at 5 C for 30 minutes. A solution of the amine (R)-ll (16.5 kg, 62.1 mol) and triethylamine (13.19 kg, 130.0 mol) in DCM (~8 L) was added to the acid chloride over 30 minutes, keeping the internal temperature less than 15 C, The resulting slurry was aged for 30 minutes and then quenched by the addition of water (167 L) over 10 minutes, keeping the internal temperature <15 C. The lower organic layer was removed, and then concentrated under atmospheric pressure to a volume of 100 L. Assay at this stage showed 27.3 kg 1, 98%. The solution was solvent switched to MeCN (ca. 560 L, 20 mL/g) by distillation under reduced pressure at <50 C. The MeCN solution was treated with ecosorb C-941 (2.8 kg) slurried in MeCN (10 L). The resulting slurry was aged for 30 min then filtered through a Solka Flok pad and a 0.1 um cartridge filter washing with MeCN (2 x 30 L). The MeCN filtrate was concentrated under reduced pressure at <50 C to a final volume of ca 112 L. The slurry was cooled to 25 C and water (280 L) added over 40 minutes. The resulting slurry was aged at 20 C for 1 hour, then filtered, washing the cake with 5:1 water: MeCN (60 L) followed by water (40 L). The solid was dried in the vacuum oven with nitrogen purge overnight at 50 C. The final target 1 was isolated as a white solid, 26.72 kg, 95%, 98.5% ee, 99.6 LCAP. m.p. 153.1 C.[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

Synthetic Route of 15988-11-1, 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. 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

General procedure: General procedure for the synthesis oftriazolo[1,2-a]indazole-trione (1a-g) and2H-indazolo[2,1-b]phthalazine-triones (2a-g)To a well-ground mixture of arylaldehyde (1 mmol), dimedone(0.140 g, 1 mmol) and 4-phenylurazole (0.177 g, 1 mmol) or2,3-dihydrophthalazine-1,4-dione (0.162 g, 1 mmol), was added[Et3N-SO3H]HSO4[(0.028 g, 0.1 mmol) for the preparation of1a-gor (0.042 g, 0.15 mmol] for the synthesis of2a-g}. Theobtained mixture was firstly stirred magnetically at 90C, andafter solidification of the reaction mixture, it was stirred with asmall rod at same temperature. After the reaction was completed(as observed by TLC), the reaction mixture was cooled to roomtemperature, water (2 mL) was added, stirred for 3 min, andfiltered. The solid residue was recrystallized from EtOH/H2O(4/1) to give the pure product.

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-Phenyl-1,2,4-triazolidine-3,5-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zare, Abdolkarim; Masihpour, Fatemeh; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 191; 8; (2016); p. 1160 – 1165;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 6523-49-5,Some common heterocyclic compound, 6523-49-5, name is 4-(1,2,4-Triazol-1-yl)aniline, molecular formula is C8H8N4, 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 mixture of forniamidine from Step 1 (200 mg) and 4-triazolyl-aniline(112 mg, 1 eq) in AcOH (2 ml) was heated to 80 for 16 h. Cooled, concentrated and cautiously treated with sodium bicarbonate (aq). The resulting solid was isolated by filtration, washed with water then DCM:EtOH:NH3 (20:8:1) added and refiltered. The filtrate was concentrated until a precipitate formed which was filtered, washed with ether and dried to give the title compound (129mg, 47%).1H NMR delta 10.06 (IH, s), 9.29 (IH, s), 8.81 (IH, s), 8.63 (IH, s), 8.23 (2H, m),8.07 (2H, d, J 10.0Hz), 7.93 (IH, s), 7.88 (2H, m), 7.83 (IH, m), 7.73 (IH, d, J7.50Hz), 7.35 (IH, t, J 8.75Hz), 3.92 (3H, s); LC-MS rt 2.42 m/z 413 ES+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-(1,2,4-Triazol-1-yl)aniline, its application will become more common.

Reference:
Patent; ARROW THERAPEUTICS LIMITED; WO2007/80401; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-65-5, These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, 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.

a 3-Methyl-3 H-1,2,3-triazole-4-carboxaldehyde To a stirred solution of 1-methyl-1 H-1,2,3-triazole (0.500 g, 6.02 mmol) in anhydrous THF (20 ml), cooled to -70 C. under nitrogen, was added dropwise a 1.6 M solution of butyl lithium in hexanes (4.23 ml, 6.77 mmol). The mixture was stirred at this temperature for 1 h, then anhydrous DMF (0.465 ml, 6.02 mmol) was added, and the mixture was allowed to warm to 0 C. over 30 min. Saturated aqueous NH4Cl (25 ml) was then added and the mixture was extracted with ethyl acetate. The organic layer was dried (Na2SO4) and evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 40% EtOAc/hexane) to give 0.128 g (19%) of the title compound as a yellow oil: 1H NMR (360 MHz, d6-DMSO) delta4.27 (3 H, s), 8.45 (1 H, s), 10.01 (1 H, s); MS (ES+) m/e 144[M+MeOH+H]+, 111[M]+.

Statistics shows that 1-Methyl-1H-1,2,3-triazole is playing an increasingly important role. we look forward to future research findings about 16681-65-5.

Reference:
Patent; Merck Sharp & Dohme Limited; US6255305; (2001); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7411-23-6, name is 3,5-Dibromo-1H-1,2,4-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. Quality Control of 3,5-Dibromo-1H-1,2,4-triazole

General procedure: 3,5-Dibromo-1,2,4-triazole (1; 658 mg, 2.9 mmol) or 3-chloro-1,2,4-triazole (300 mg, 2.9 mmol), o-quinone methide precursor 2 (2.9mmol), and K2CO3 (1.2 g, 8.7 mmol) were refluxed for 4 h in DMF (10mL). After completion of the reaction, the mixture was cooled, andpoured into H2O (30 mL). The precipitate formed was collected by filtration,washed with H2O, dried, and recrystallized.

The synthetic route of 7411-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Osipov, Dmitry V.; Osyanin, Vitaly A.; Voskressensky, Leonid G.; Klimochkin, Yuri N.; Synthesis; vol. 49; 10; (2017); p. 2286 – 2296;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics