Triazoles

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. 105020-39-1, name is Methyl 2-Methyl-1,2,3-triazole-4-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 2-Methyl-1,2,3-triazole-4-carboxylate

Step2:; 2-methyl 2H-1 ,2,3-triazole-4-carboxylic acid methyl ester (263 mg, 1 .86 mmol) is charged in a round-bottom flask, then THF (15 mL), 1 M solution NaOH (9.3 mL, 9.3 mmol, 5.0 equiv) and MeOH (5 mL) are measured and mixed in a graduated cylinder, then added to flask. Solution is stirred at room temperature. After 4 h, 1 M HCI is added (10 mL) and solvent is evaporated. EtOAc is added and layers are separated. Solvent is evaporated. Desired product R2I is obtained as a white solid (215 mg, 91 %).1H NMR (400 MHz,DMSO-d6): delta 8.17 (s, 1 H), 4.22 (s, 3H).

According to the analysis of related databases, 105020-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; LLINAS-BRUNET , Montse; BORDELEAU, Josee; GODBOUT, Cedrickx; LEBLANC, Melissa; MOREAU, Benoit; O’MEARA, Jeffrey; WO2011/63502; (2011); 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

Related Products of 4923-01-7, 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. 4923-01-7, name is 5-Methyl-4H-1,2,4-triazol-3-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below.

[0163] Synthesis of 2,5-Dimethyl-[l,2,4]triazolo[l,5-alpha]pyrimidin-7-yI)-naphthalen-2- yl-amine.; [0164] This compound is synthesized according the scheme above and is characterized as follows: melting point: 84C. 1H NMR (300 MHz, DMSO-d6): delta 10.32 (brs, NH, exchangeable), 8.05-7.90 (m, 4H), 7.52-7.60 (m, 3H), 6.48 (s, IH), 2.50 (s, 3H), 2.36 (s, 3H). MS m/z 290.1 (M + H+).

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, 5-Methyl-4H-1,2,4-triazol-3-amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOARD OF REGENTS, UNIVERSITY OF TEXAS SYSTEM; UNIVERSITY OF WASHINGTON; WO2009/82691; (2009); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 7170-01-6, 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. 7170-01-6 name is 3-Methyl-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.

A solution of 2,4-difluorobenzonitrile (7.07 g, 50.8 mmol) and 3-methyl-1H-1,2,4-triazole (4.22 g, 50.8 mmol) in N,N-dimethylformamide (45 ml) was treated with powdered anhydrous potassium carbonate (10 g) and the resulting mixture stirred at 22 C. for 18 h. The solid was then filtered and the filtrate concentrated in vacuo. The residue was diluted with ethyl acetate, washed with water and brine, then dried over anhydrous magnesium sulfate and concentrated. The resulting mixture was purified by a combination of chromatography on silica gel (elution gradient of ethyl acetate in hexane) and reversed phase silica gel to yield intermediates 45-48. 4Fluoro-2-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate-hexane); mp 117-118 C. 1HNMR 400 MHz (CDCl3) delta ppm: 2.54 (3H, s, CH3), 7.24 (1H, m, CH), 7.62 (1H, dd, J=2.5 Hz and J=9.1 Hz, CH), 7.84 (1H, dd, J=5.6 Hz and J=8.6 Hz, CH), 8.82 (1H, s, CH). Anal. Calcd for C10H7FN4: C 59.40, H 3.49, N 27.71; Found: C 59.25, H 3.32, N 27.81. 4-Fluoro-2-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate-hexane); mp 120-121 C. 1HNMR400 MHz (CDCl3) delta ppm: 2.56 (3H, s, CH3), 7.30 (1H, dd, J=2.5 Hz and J=8.1 Hz, CH), 7.39 (1H, m, CH), 7.91 (1H, dd, J=5.5 Hz and J=8.6 Hz, CH), 8.06 (1H, s, CH). Anal. Calcd for C10H7FN4: C 59.40, H 3.49, N 27.71; Found: C 59.35, H 3.70, N 27.77. 2-Fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate-hexane); mp 133-134 C. 1HNMR 400 MHz (CDCl3) delta ppm: 2.52 (3H, s, CH3), 7.61 (1H, dd, J=2 Hz and J=9.1 Hz, CH), 7.67 (1H, dd, J=2 Hz and J=9.6 Hz, CH), 7.79 (1H, dd, J=6.5 Hz and J=8.6 Hz, CH), 8.56 (1H, s, CH). Anal. Calcd for C10H7FN4: C 59.40, H 3.49, N 27.71; Found: C 59.42, H 3.24, N 28.41. 2-Fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)benzonitrile. White crystals (ethyl acetate-hexane); mp 89-90 C., 1HNMR 400 MHz (CDCl3) delta ppm: 2.69 (3H, s, CH3), 7.49-7.55 (2H, m, 2 x CH), 7.83 (1H, dd, J=6.8 Hz and J=8.8 Hz, CH), 8.00 (1H, s, CH). Anal. Calcd for C10H7FN4: C 59.40, H 3.49, N 27.71; Found: C 59.17, H 3.22, N 28.01.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Methyl-1H-1,2,4-triazole, and friends who are interested can also refer to it.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/111984; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 217448-86-7,Some common heterocyclic compound, 217448-86-7, name is Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate, molecular formula is C11H9F2N3O2, 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.

Example-4 Preparation of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylic acid A mixture of Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate. (50 gms) and a solution of sodium hydroxide (11.76 gms in 100 ml water) were stirred at room temperature contents till it becomes clear. Hydrochloric acid (30 ml ) in DM water (70 ml) was charged to above reaction mass. Adjusted the PH of the reaction till 2-3 by adding the hydrochloric acid solution at 25-30 C. After the completion, reaction mass was filtered and dried the material at 65 C.-70 C. for 15 hours. Yield: 40 gms

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxylate, its application will become more common.

Reference:
Patent; Davuluri, Ramamohan Rao; Ponnaiah, Ravi; Dehury, Sanjay Kumar; K., Selvaraju; VPSS, Deepthi; Naidu, Dhanunjaya; US2013/184469; (2013); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 3641-13-2, 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 3641-13-2 as follows.

General procedure: A mixture of benzil (0.01 mol), aldehydes (0.01 mol), 3-amino-1,2,4-triazole-5-carboxylic acid (0.01 mol), ammonium acetate (0.01 mol) and ceric ammonium nitrate (15 mol%) as a catalyst were refluxed in ethanol (15 mL) for about 3-4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was cooled to room temperature. The solid formed was filtered and dried. The crude products were recrystallized by ethanol.

According to the analysis of related databases, 3641-13-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nikalje, Anna Pratima G.; Ghodke, Mangesh S.; Kalam Khan, Firoz A.; Sangshetti, Jaiprakash N.; Chinese Chemical Letters; vol. 26; 1; (2015); p. 108 – 112;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 27808-16-8, 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. 27808-16-8, name is 4-Methyl-1H-1,2,3-triazole, This compound has unique chemical properties. The synthetic route is as follows.

Description D34: methyl 6-methyl-3-(4-methyl-2H-l,2,3-triazol-2-yl)-2- pyridinecarboxylate (D34); DMF (1.5 ml) was added to a mixture of methyl 3-iodo-6-methyl-2-pyridinecarboxylate D27 (200 mg), 4-methyl-lEta-l,2,3-triazole (120 mg, 1.444 mmol), (lR,2R)-N,N’-dimethyl- 1 ,2-cyclohexanediamine (20.54 mg, 0.144 mmol), copper(I) trifluoromethanesulfonate benzene complex (18.17 mg, 0.036 mmol) and cesium carbonate (470 mg, 1.444 mmol) in a screw-topped vial. The mixture was degassed via 3 vacuum/nitrogen cycles and heated with shaking in a PLS reaction station to 120 0C for 5 hours. The reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in water/MeOH (1 :1, 3 ml) and acidified to pH=2 by addition of 2 M HCl solution. The resulting mixture was evaporated to dryness under reduced pressure then the residue was triturated with DCM/MeOH (3:1, 5 ml). The mixture was filtered washing with more DCM/MeOH (3:1, 5 ml). The filtrate was treated with TMS-diazomethane solution 2 M in hexane (4 ml, 8 mmol) to re-esterify the acid. The reaction mixture was evaporated under reduced pressure and the residue was purified via Biotage (20%-50% EtOAc/cyclohexane; SNAP 25 silica column) to give the title compound D34 (121 mg) as colourless solid.UPLC (Acid QC POS 50-800): rt = 0.59 minutes, peak observed: 233 (M+l) C11H12N4O2 requires 232. 1H NMR (400 MHz, CDCl3y) delta ppm 8.15 (d, 1 H), 7.59 (s, 1 H), 7.37 (d, 1 H), 3.92 (s, 3 H), 2.66 (s, 3 H), 2.40 (s, 3 H).

The chemical industry reduces the impact on the environment during synthesis 4-Methyl-1H-1,2,3-triazole. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; AMANTINI, David; DI FABIO, Romano; WO2010/122151; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 4928-87-4, These common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, 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: Single crystals of 1 were prepared by a branched tube method [34], 1H-1,2,4-triazole-3-carboxylic acid (0.117 g, 1 mmol), lead(II) nitrate (0.331 g, 1 mmol) and potassium bromide (0.119 g, 1 mmol) were placed in the bottom main of a branched tube. Water was carefully added to fill both arms, and then the arm to be heated was placed in oil bath at 60 C. After 7 days, colorless crystals were deposited in the cooler arm which were filtered off, washed with water and air dried. (0.225 g, yield 54%),

The synthetic route of 4928-87-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Safarifard, Vahid; Morsali, Ali; Inorganica Chimica Acta; vol. 405; (2013); p. 203 – 208;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7170-01-6,Some common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, molecular formula is C3H5N3, 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) 1-(2-Fluoro-4-nitro-phenyl)-5-methyl-1H-[1,2,4]triazole; 3,4-Difluoronitrobenzene (514 mg, 3.23 mmol), 3-methyl-1H-1,2,4-triazole (325 mg, 3.72 mmol) and di-potassium hydrogen phosphate trihydrate (1.49 g, 6.46 mmol) in dimethyl sulfoxide (1.5 mL) were stirred for 6 hours at 70 C. The mixture was concentrated in vacuo; the residue was diluted in water and extracted three times with ethyl acetate. The combined organic layers were washed four times with water, twice with brine, dried with magnesium sulfate and evaporated. Column chromatography (30 g silica, heptane/ethyl acetate 1:1 v/v) afforded the title compound (160 mg, 22%) as white crystals MS ISP (m/e): 223.2[(M+H)+]. 1H NMR (CDCl3, 300 MHz): delta (ppm)=8.22 (m, 2H), 8.04 (s, 1H), 7.74 (dd, 1H), 2.48 (d, 3H). Mp 56-58 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methyl-1H-1,2,4-triazole, its application will become more common.

Reference:
Patent; Baumann, Karlheinz; Flohr, Alexander; Goetschi, Erwin; Jacobsen, Helmut; Jolidon, Synese; Luebbers, Thomas; US2009/215759; (2009); 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 3179-31-5 as follows. name: 1H-1,2,4-Triazole-3-thiol

To a solution of 1-(benzenesulfonyloxyoctyl)-cyclopropene (480 mg, 1.55 mmol) in about 2 ml N,N-dimethylformamide was added potassium t-butoxide (19.8% in tetrahydrofuran, 734 mg, 1.55 mmol) and 1H-1,2,4-triazole-3-thiol (172 mg, 1.71 mmol.) After stirring at room temperature for about 2 hours, sodium iodide (87.7 mg, 0.775 mmol) was added. After the reaction was heated to about 50 C. for about 2 hours, water and ethyl acetate were added then the phases were separated. The isolated organic layer was washed twice with water, dried over magnesium sulfate and concentrated in vacuo. This residue was purified by column chromatography on silica gel using hexanes/ethyl acetate to give 30 mg of 70% pure 1-(1H-1,2,4-triazol-2-ylthiooctyl)-cyclopropene as an oil.

According to the analysis of related databases, 3179-31-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jacobson, Richard Martin; Kelly, Martha Jean; Wehmeyer, Fiona Linette; Evans, Karen Anderson; US2005/65033; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics