Category: Triazoles

New discoveries in chemical research and development in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 4922-98-9, name is 5-Phenyl-1H-1,2,4-triazol-3-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Safety of 5-Phenyl-1H-1,2,4-triazol-3-amine

General procedure: 4.1.1.1. General procedure. An equimolar mixture of compound 3, 7a-c and N-(4-acetylphenyl)-2-bromoacetamide 9 (0.25 g,1 mmol) in acetonitrile (50 ml) and TEA (0.10 g, 1.2 mmol) was heated at reflux for 4-8 h. The reaction mixture was evaporated to dryness. The residue was crystallized from aqueous ethanol affording products 10a-d.

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Reference:
Article; El-Sherief, Hany A.M.; Youssif, Bahaa G.M.; Abbas Bukhari, Syed Nasir; Abdelazeem, Ahmed H.; Abdel-Aziz, Mohamed; Abdel-Rahman, Hamdy M.; European Journal of Medicinal Chemistry; vol. 156; (2018); p. 774 – 789;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. name: 3,5-Dibromo-1H-1,2,4-triazole

To a solution of 3,5-dibromo-lh-1,2,4-triazole (150.0 g, 661.2 mmol) in tetrahydrofuran (1500 mL) was slowly added p-toluenesulfonic acid (17.1 g, 99.2 mmol), followed by 3,4-dihydro-2h-pyran (166.9 g, 1983.6 mmol) at 0 C. After addition, the reaction mixture was heated at 70 C for 3h and concentrated under reduced pressure. The residue was poured into water (500 mL) and adjusted to pH = 9 by addition of saturated aqueous sodium bicarbonate. The resulting mixture was extractedwith ethyl acetate (3 x 400 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduce pressure. The resulting cmde product was washed with methanol (2 x 50mL), dried under reduced pressure to give crude 3,5-dibromo-1-tetrahydropyran-2-yl-1,2,4-triazole (155 g, 75%) as a white solid. ?H NMR (400 MHz, CDC13) 5 5.49 – 5.46 (m, 1H), 4.12 – 3.99 (m, 1H), 3.72 – 3.61 (m, 1H), 2.38 – 2.26 (m, 1H), 2.18 -2.07 (m, 1H), 1.98 – 1.90 (m, 1H), 1.78 – 1.60 (m, 3H).

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 3,5-Dibromo-1H-1,2,4-triazole, in my other articles.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; PATEL, Snahel; (77 pag.)WO2019/204537; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 118863-62-0, New Advances in Chemical Research in 2021.In classical electrochemical theory, both the electron transfer rate and the adsorption of reactants at the electrode control the electrochemical reaction. 118863-62-0, name is 3-(4-Bromophenyl)-1H-[1,2,4]triazole, molecular formula is C8H6BrN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

A solution of 3-(4-bromophenyl)-lH-l,2,4-triazole (10.9 g, 48.5 mmol), l-iodo-4-(trifluoromethoxy)benzene (13.2 g, 45.8 mmol), copper(I) iodide (2.38 g, 12.5 mmol), and cesium carbonate (30.3 g, 93.0 mmol) in dimethylsulfoxide (85 mL) was degassed with nitrogen for 5 minutes. The mixture was heated at 100 C for 60 hours. After cooling, ethyl acetate (200 mL) was added and the mixture was filtered through Celite. The filtrate was added to a solution of saturated ammonium chloride (200 mL) and stirred for one and a half hours. The layers were separated and the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and adsorbed onto Celite. Purification by flash column chromatography using 0-40% ethyl acetate/hexanes as eluent provided the title molecule as an off-white solid (9.65 g, 52%) : mp 109-112 C; XH NMR (400 MHz, CDCI3) delta 8.56 (s, 1H), 8.10-8.03 (m, 2H), 7.83-7.75 (m, 2H), 7.64-7.57 (m, 2H), 7.42-7.35 (m, 2H); ESIMS m/z 384 ([M + H]+).

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Reference:
Patent; DOW AGROSCIENCES LLC; GIAMPIETRO, Natalie C.; BAUM, Erich W.; FISCHER, Lindsey G.; GOLDSMITH, Miriam E.; CROUSE, Gary D.; RENGA, James M.; SPARKS, Thomas C.; (234 pag.)WO2016/99929; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 1186050-58-7, New discoveries in chemical research and development in 2021. We’ll be discussing some of the latest developments in chemical about CAS: 1186050-58-7, name is 2-Fluoro-6-(2H-1,2,3-triazol-2-yl)benzoic 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.

Compound 9-2 (120 mg, 0.32 mmol), compound 9-3 (77 mg, 0.38 mmol), HATU (182 mg, 0.48 mmol) and DIEA (124mg, 0.96 mmol) were dissolved in 5 mL of DMF, and the mixture was stirred under room temperature for 3 hours. The reaction mixture was poured into aqueous saline and extracted with ethyl acetate (10 mL x 3). The organic phase was combined and washed with water (10 mL x 2) and saturated NaCl solution (10 mL x 2), dried with anhydrous Na2SO4, filtered, and concentrated to obtain a crude product. The crude product was purified with preparative HPLC to give product 9-4 (22 mg, white solid, yield: 21 %). 1H NMR (400 MHz, MeOD) delta= 8.20-7.98 (m, 3H), 7.85-7.72 (m, 1H), 7.71-7.50 (m, 2H), 7.48-7.17 (m, 1H), 7.03-6.75 (m, 1H), 4.87-4.66 (m, 1H), 4.54-4.36 (m, 1H), 4.31-4.05 (m, 1H), 3.86-3.55 (m, 1H), 2.14 (br. s., 1H), 2.08-1.95 (m, 1H), 1.88 (td, J=7.2, 19.8 Hz, 2H), 1.77 (dd, J=11.3, 18.1 Hz, 2H), 1.68-1.54 (m, 1H), 1.53-1.32 (m, 2H)

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Reference:
Patent; Shanghai Haiyan Pharmaceutical Technology Co. Ltd.; Yangtze River Pharmaceutical Group Co., Ltd.; HE, Haiying; WU, Songliang; ZHANG, Yang; MA, Biao; CHEN, Yuan; WANG, Yuhe; CHEN, Shuhui; LV, Qiang; LAN, Jiong; LIU, Xing; (54 pag.)EP3115362; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 288-36-8, New Advances in Chemical Research in 2021.Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media, 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, below Introduce a new synthetic route.

1,2,3-triazole(0.7 ), 2-iodo-benzoic acid (1.0 ), cesium carbonate (2.36 g, 7.20 mmol)Trans-N, N’-dimethyl-1,2-cyclohexanediamine (0.10 g, 0.75 mmol), cuprous iodide (0.08 g, 0.40 mmo 1), N, N-dimethyl Amide (18 mL)Were successively added to a 100 mL single-necked round bottom flask and gradually warmed to 100 C for 4 hours under nitrogen protection.The reaction was quenched, cooled, diluted with tap water and extracted with ethyl acetate (200 mL X).The aqueous layer was acidified with concentrated hydrochloric acid (rhoH- = 1 ~ 2) and extracted with ethyl acetate (200 mL x 2). The combined organic layers were dried and dried over anhydrous sodium sulfate. The filtrate was evaporated under reduced pressure and purified by column chromatography. (Dichloromethane / methanol (v / v) = 30/1) gave the title compound (yellow solid, 0.511 g, 67%)

In the meantime we’ve collected together some recent articles in this area about 288-36-8 to whet your appetite. Happy reading!

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Wei Dehuo; Xue Yaping; Zhang Yingjun; (44 pag.)CN106674207; (2017); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 3641-13-2, New Advances in Chemical Research in 2021.Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media, 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, molecular formula is C3H4N4O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

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.

The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis.I hope my blog about 5-Amino-4H-1,2,4-triazole-3-carboxylic acid is helpful to your research.

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

New discoveries in chemical research and development in 2021. Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. 103755-58-4, name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 103755-58-4

General procedure: Into a round-bottom flask equipped with a magnetic stirring bar already containing a solution of 10mmolof 1,2,3-triazoles type 12 in 27.5mL of DMSO was added 11mmolof IBX. This mixture was stirred at room temperature for 4h. Next, distilled water (20mL) was added, and stirring was continued for 15minat room temperature. Subsequently, the mixture was filtered, extracted with ethyl acetate and dried over with MgSO4. The product was purified via silica-gel column chromatography using gradient mixture of hexane-ethyl acetate to afford the pure derivatives 11 and 15a-b.

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Reference:
Article; Gonzaga, Daniel; Senger, Mario Roberto; Da Silva, Fernando De Carvalho; Ferreira, Vitor Francisco; Silva Jr., Floriano Paes; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 461 – 476;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 61-82-5, New Advances in Chemical Research in 2021. The prevalence of solvent effects in heterogeneous catalysis in condensed media has motivated developing quantitative kinetic,A common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

General procedure: A mixture of aromaticaldehyde (1.0 mmol) and dimedone(1.0 mmol) with 2-aminobenzimidazole or 3-amino-1,2,4-triazole (1.0 mmol) was stirred in acetic acid (5 mL) at 60 Cfor the appropriate time (Tables 3, 4). The progress of thereaction was monitored by TLC. After completion of thereaction, a thick precipitate was obtained. The solid productwas filtered off and washed with acetic acid (3 × 2 mL) togive the pure products 4 and 6, and subsequently dried in air.The pure products were characterized by conventional spectroscopicmethods. Physical and spectral data for the compounds,4b, 4c, 4h, 4j, 6a, 6c, and 6h are represented below:

I am very proud of our efforts over the past few months and hope to 1H-1,2,4-Triazol-5-amine help many people in the next few years.

Reference:
Article; Mousavi, Mir Rasul; Maghsoodlou, Malek Taher; Hazeri, Nourallah; Habibi-Khorassani, Sayyed Mostafa; Journal of the Iranian Chemical Society; vol. 12; 8; (2015); p. 1419 – 1424;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2, New Advances in Chemical Research in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid, molecular formula is C3H3N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

To a stirred solution of 504 mg (2 mmol) 8-(phenylsulfonyl)-3,8- diazabicyclo[3.2.1 ]octane (Intermediate 2) in 6 mL NMP were added at RT 452 mg (2 eq, 4 mmol) 1 H-1 ,2,3-triazole-5-carboxylic acid, 1045 mu (3 eq, 6 mmol) DIPEA and 1 .52 g (2 eq, 4 mmol) HATU and the mixture was stirred for 6 h. The mixture was taken up in ethyl acetate, washed with water, dried with sodium sulfate, evaporated and the residue was subjected to flash chromatography using ethyl acetate and hexane to yield 787 mg (1 .93 mmol, 96 %) of the title compound 3,8-diazabicyclo[3.2.1 ]oct-3-yl(1 H- 1 ,2,3-triazol-4-yl)methanone.

We very much hope you enjoy reading the articles and that you will join us to present your own research about 16681-70-2, Happy reading!

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; KOPPITZ, Marcus; SIEBENEICHER, Holger; STEUBER, Holger; TER LAAK, Antonius; NUBBEMEYER, Reinhard; ROTTMANN, Antje; IRLBACHER, Horst; BADER, Benjamin; PETERS, Michaele; WAGENFELD, Andrea; TEREBESI, Ildiko; (123 pag.)WO2017/202817; (2017); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 16681-65-5, New Advances in Chemical Research in 2021. The dynamic chemical diversity of the numerous elements, ions and molecules that constitute the basis of life provides wide challenges and opportunities for research. 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, molecular formula is C3H5N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

A 50 mL flask containing 1-methyl-1H-1,2,3-triazole (0.47 g, 5.71 mmol) in dry THF (3 mL) was cooled to -43 C. (CH3CN-CO2 bath). n-Butyllithium (2.5 M in THF, 2.43 mL, 6.08 mmol) was then added dropwise resulting in a light blue suspension. The suspension was stirred at -40 C. for 40 minutes, and then a homogeneous solution of 6-(trifluoromethyl)nicotinaldehyde (1 g, 5.71 mmol) in THF (7 mL) was introduced at -40 C. The resulting homogeneous colorless solution was allowed to warm gradually to room temperature, and after 30 minutes, LC/MS showed that the reaction was complete. The mixture was quenched with water and aqueous NH4Cl and extracted with EtOAc (2*). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated to provide the title compound as a semi-solid which was carried on to the next step without further purification.

By the way, if you are interested in learning more fun chemistry with your kids, get your hands into one chemistry set now, and start enjoying the best part of chemistry: experiments about 1-Methyl-1H-1,2,3-triazole.

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; US2015/105366; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics