Category: Triazoles

Some common heterocyclic compound, 64922-04-9, name is Ethyl 1H-1,2,4-triazole-5-carboxylate, molecular formula is C5H7N3O2, 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. 64922-04-9

Example 1.10: Preparation of l-ethyl-lH-[l,2,,4~|triazole~3-carboxyric acid methyl ester and 1 -ethyl- IH-[1, 2,4]triazole-5-carboxylic acid methyl esterTo a suspension of IH-[1, 2,4]-triazole-3-carboxylic acid methyl ester (25 g, commercially available) in dry lambdazetaN-dimethylformamide (200 ml) at O0C under an atmosphere of nitrogen was added in portions sodium hydride (60% by weight dispersion in mineral oil) (8.66 g). On complete addition, the mixture was stirred for 1 hour at ambient temperature then re-cooled to O0C and ethyl iodide (15.5 ml) was added. The reaction mixture was stirred for 1 hour, stored for 18 hours then treated with aqueous ammonium chloride (IM) and concentrated to give a yellow oil. The oil was dissolved in chloroform (300 ml), washed with water (100 ml), dried over magnesium sulfate and concentrated. The oil that remained was washed with hexane and then triturated with diethyl ether to give a mixture of l-ethyl-lH-[l,2,4]triazole-3-carboxylic acid methyl ester and 1 -ethyl- IH-[1, 2,4]triazole-5-carboxylic acid methyl ester which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64922-04-9, its application will become more common.

Reference:
Patent; SYNGENTA LIMITED; WO2008/74991; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine, 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 4922-98-9. 4922-98-9

Example 11; Part A; A reaction mixture of 3-phenyl-1 H-1 ,2,4-tpiazol-5-amiotane (160 mg, 1 mmol) and dimethyl but-2-ynediotaoate (123 mul_, 1 mmol) in methanol (2 ml_) was stirred at room temperature for overnight Purification using reverse phase HPLC gave compound 11-1 as a solid after lyophilization HPLC-MS RT= 3 08 mm, mass calculated for formula Ci3H10N4O3270 08, observed LCMS m/z 271 28 (M+H)

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 5-Phenyl-1H-1,2,4-triazol-3-amine.

Reference:
Patent; SCHERING CORPORATION; SHIPPS, JR., Gerald, W.; CHENG, Cliff, C.; HUANG, Xiaohua; ACHAB, Abdelghani, Abe; ORTH, Peter; VOIGT, Johannes, H.; SOUCY, Kyle, Ann; WO2010/56631; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

13273-53-5, 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. 13273-53-5, name is 4-Bromo-1-methyl-1H-1,2,3-triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

In a microwave tube to a mixture of 3,3-dimethyl-6-(2-methylpyrimidin-5-yl)indolin-2-one (100 mg, 395 imol, Eq: 1.00, cf. Example 70 step c) and 4-bromo-1-methyl-1H-1,2,3-triazole (76.7 mg, 474 imol, Eq: 1.2) was added acetonitrile (3 ml). The solvent was degassed by bubbling nitrogen through the suspension for 10 minutes. Then was added at 22 C N,N?5 dimethylethylenediamine (6.96 mg, 8.5 jil, 79.0 imol, Eq: 0.2) followed by potassium carbonate(136 mg, 987 imol, Eq: 2.5) and copper (I) iodide (7.52 mg, 39.5 imol, Eq: 0.1). The tube was inerted, sealed and the mixture was heated in microwave at 170C for 30 minutes.The mixture was treated with 2 ml of water and extracted with ethyl acetate (2 x 2 ml). The organic layers were dried, filtered and concentrated in vacuo.The residue was purified by chromatography on silica gel to give the desired compound as a white solid (8 mg, 6%). MS (mlz) = 335.2 [M + H].

The synthetic route of 4-Bromo-1-methyl-1H-1,2,3-triazole has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HILPERT, Hans; KOLCZEWSKI, Sabine; HUMM, Roland; STOLL, Theodor; MUSER, Thorsten; PLANCHER, Jean-Marc; GAUFRETEAU, Delphine; (142 pag.)WO2015/197567; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

13273-53-5, 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 13273-53-5 as follows.

Example 212 (5alpha,8alpha)-8-(5-Bromo-3-methyl-3H-[1,2,3]triazol-4-yl)-8-hydroxy-2-(4-isopropoxy-phenyl)-2-aza-spiro[4.5]decan-1-one A solution of 4-bromo-1-methyl-1H-1,2,3-triazole (108 mg) in tetrahyrofurane (5 mL) was cooled to -78 C. under an argon atmosphere and then treated dropwise with n-butyllitium (415 mul, 1.6 M in hexanes) over 10 minutes. The reaction mixture was stirred 15 min at -78 C., then treated dropwise with 2-(4-isopropoxyphenyl)-2-aza-spiro[4.5]decane-1,8-dione (200 mg in 3 ml tetrahydrofuran, product of example 184, step 2). The mixture was stirred further 1 h at -78 C. then warmed slowly to RT. It was then partitioned between AcOEt and saturated aqueous NH4Cl, the layers were separated, the organic layer washes with 1M aqueous HCL then brine and dried over Na2SO4. The solvent was evaporated off the residue purified by flash chromatography (silica gel, gradient of methylene chloride and AcOEt) to give the title compound (102 mg, 31%) as a white solid. MS (m/e): 465.131 [MH+].

According to the analysis of related databases, 13273-53-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ackermann, Jean; Brugger, Stephan; Conte, Aurelia; Hunziker, Daniel; Neidhart, Werner; Nettekoven, Matthias; Schulz-Gasch, Tanja; Wertheimer, Stanley; US2011/92512; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

135242-93-2, A common heterocyclic compound, 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol, molecular formula is C4H7N3O, 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.

6-Cyclobutyl-3-(2-fluorophenyl)-4H-1,2,3-triazolo[1,5-alpha]pyrimidin-5-one (50 g, 0.18 mmol), triphenylphosphine (120 mg, 0.44 mmol) and (1-methyl-1H-1,2,4-triazol-3-yl)methanol (50 g, 0.44 mmol) were suspended in dry tetrahydrofuran (1.5 ml).. diethyl azodicarboxylate (70 mul, 0.44 mmol) was added and a solution resulted immediately.. The reaction was stirred at room temperature for 48 hours during which time a precipitate formed in the reaction mixture.. The crude reaction mixture was evaporated and recrystallized from EtOAc. The pale pink crystalline solid thus produced was collected by filtration and washed with diethyl ether to afford 6-cyclobutyl-3-(2-fluorophenyl)-5-(1-methyl-1H-1,2,4-triazol-3-ylmethoxy)-1,2,3-triazolo[1,5-alpha]pyrimidine (40 mg, 60%) as pale needles, m.p. 202-205 C.; deltaH (400 MHz, CDCl3) 1.84-1.92 (1H, m, CH(CH2)3), 2.06-2.16 (3H, m, CH(CH2)3), 3.67 (1H, quintet, J=9 Hz, CH(CH2)3), 3.94 (3H, s, NCH3), 7.19-7.29 (2H, m, ArH), 7.32-7.36 (1H, m, ArH), 8.04 (1H, s, triazole CH), 8.12 (1H, td, J=7.5 and 1.8 Hz, ArH), 8.55 (1H, d, J=1.5 Hz, pyrimidine CH); m/z (ES+) 380 (M+H+).

The synthetic route of 135242-93-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Ltd.; US6337331; (2002); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, 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 1001401-62-2. 1001401-62-2

(S) – /ert-butyl 3-methyl-4-r5-methyl-2-(2H-1.2.3-triazol-2-v?benzoyll-1.4-diazepane-l- carboxylate (D-5)To a solution of 400 mg (1.87 mmol) D-4, 371 mg (1.96 mmol) B-3, 343 mg(2.24 mmol) 1-hydroxybenzotriazole hydrate, and 780 muL (5.6 mmol) triethylamine in 5 mL of DMF was added 537 mg (2.8 mmol) EDC and the reaction was stirred overnight at 500C. The reaction was partitioned between EtOAc and saturated aqueous NaetaCtheta3. The layers were separated and the organic was washed with water, brine, dried over MgSO4 and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel (EtOAc/hexanes) to provide D-5 as a colorless gum. Data for D-5: LC/MS: rt = 2.09 min; m/z (M + H) = 386.1, found; 386.2 required.

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 2-(2H-1,2,3-Triazol-2-yl)benzoic acid.

Reference:
Patent; MERCK & CO., INC.; WO2008/8518; (2008); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, 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 23579-79-5. 23579-79-5

A mixture of 1,2,3,4-tetrahydroisoquinoline (1.1 g, 8.3 mmol), intermediate 32 (0.2 g, 8.3 mmol), K2CO3 (2.3 g, 16.6 mmol) in DMF (20 ml) was heated at 160 C. for 45 min using microwave irradiation. The r.m. was cooled and then poured onto H2O and extracted with DCM. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel (eluent: DCM/MeOH from 100/0 to 97/3). The product fractions were collected and concentrated in vacuo, yielding 900 mg of intermediate 33 (40%).

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 3,5-Dibromo-1-methyl-1H-1,2,4-triazole.

Reference:
Patent; Van Brandt, Sven Franciscus Anna; De Cleyn, Michel Anna Jozef; Gijsen, Henricus Jacobus Maria; Berthelot, Didier Jean-Claude; Surkyn, Michel; US2012/295891; (2012); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 13423-60-4 name is 1-Phenyl-1H-1,2,4-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. 13423-60-4

To 10 mL of chlorosulfonic acid at 0 C was added 1 g (6.9 mmol) of1-phenyl-1H-1,2,4-triazole, 35. The mixture was stirred overnight andthen cooled to 0 C. The solution was slowly added to ice and extracted3 three times with dichloromethane. The organic layers were combined,dried over sodium sulfate and concentrated to dryness in vacuo to give1 g of a tan solid. The crude sulfonyl chloride was used directlywithout further purification. To a microwave vial was added 25 mg(0.095 mmol) of the sulfonyl chloride, 15 mg (0.11 mmol) of 1,2,3,4-tetrahydroquinoline, 14 mg (0.014 mmol) of triethylamine and 300 muLof acetonitrile. The vial was sealed and heated at 130 C for 30 min. Themixture was diluted with dichloromethane and the organic phase waswashed 2 times with water and brine. The organic layer was dried oversodium sulfate and concentrated in vacuo. The crude sulfonamide waspurified by flash chromatography 0-75% EtOAc/Hexanes.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Phenyl-1H-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Article; Okolotowicz, Karl J.; Dwyer, Mary; Ryan, Daniel; Cheng, Jiongjia; Cashman, Emily A.; Moore, Stephanie; Mercola, Mark; Cashman, John R.; Bioorganic and Medicinal Chemistry; vol. 26; 15; (2018); p. 4441 – 4451;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common compound: 1455-77-2, name is 3,5-Diamino-1,2,4-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. 1455-77-2

To a methanolic solution (15mL) of 9 3,5-diamino-1,2,4-triazole (0.099g, 1mmol) an equimolar solution of 10 2-chlorobenzaldehyde (0.141g, 1mmol) was added and the mixture was first stirred at room temperature for 30min and then refluxed for 5?6h. The excess of solvent was removed by under reduced pressure using rotavapor and then washed with methanol and recrystallized from dichloromethane – methanol. The resulted product was dried under vacuum. The synthesis scheme alongwith atom number (for assignment only) of the schiff base is presented in Scheme 1 . 2.1.2 12 (E)-N3-(2-chlorobenzylidene)-1H-1,2,4-triazole-3,5-diamine Yield: 0.157g, 71percent; colour: light yellow; m.p: 235?240¡ãC; 1H NMR (delta in ppm DMSO-d6, 500MHz): 12.10 (s, 1H, NHtriazole), 9.36 (s, 1H, H-7), 8.13 (d, 1H, J=7.5Hz, H-3), 7.53 (d, 1H, J=8Hz, H-4), 7.49 (d, 1H, J=8Hz, H-6), 7.43 (t, 1H, J=7.5Hz, H-5), 6.20 (s, 2H, NH2); 13C NMR (delta in ppm DMSO-d6/125MHz): 163.85 (C-8), 157.39 (C-7), 157.10 (C-9), 135.82 (C-2), 133.59 (C-1), 132.93 (C-3), 130.65 (C-6), 128.49 (C-4), 128.27 (C-5); FT-IR (KBr, cm?1): 3322 nuas(NH2), 3233 nu(N?H), 3149 nus(NH2), 2785 nu(C?H), 1651 nu(C=N), 681 nu(C?Cl); MS (ESI) m/z: ([M+H]+) 222.05; Anal. Calc percent for C9H8N5Cl: C, 48.76; H, 3.61; N, 31.60; Found: C, 48.50; H, 3.32; N, 31.4.

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, 1455-77-2, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Pokharia, Mamta; Yadav, Swatantra K.; Mishra, Hirdyesh; Pandey, Nidhi; Tilak, Ragini; Pokharia, Sandeep; Journal of Molecular Structure; vol. 1144; (2017); p. 324 – 337;,
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 27996-86-7 as follows. 27996-86-7

Weigh 0.173 g (1 mmol) of 4- (1-1,2,4-triazolyl) benzaldehyde,P-Phenylenediamine 0.054 g (0.500 mmol),Was dissolved in 4 mL of N, N-dimethylformamide,Add to a thermometer,Stirring device in a 10 mL single-necked flask.Then 0.120 g (2 mmol) of acetic acid was added to the above mixture,The reaction was heated at 50 8h,The solvent was distilled off under reduced pressure,A yellow powdery solid was obtained,Recrystallization and purification with ethanol,50 vacuum dried 6h to obtain the final product compound 1(Triazole benzaldehyde shrink p – phenylenediamine double Schiff base). Yield: 89%.

According to the analysis of related databases, 27996-86-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Qilu University of Technology; Duan Hongdong; Xu Ting; Bu Juan; (13 pag.)CN107056716; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics