Triazoles

Application of 288-36-8, 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. 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.

To a 100 ml round bottom flask containing 2-chloro-6-methylnicotinic acid (3 g, 17.4 mmol), copper iodide (0.16 g, 0.5 mol%), and cesium carbonate (1 1 .4 g, 35 mmol) was added a mixture of dioxane (20 ml_) and H2O (0.1 ml, 5.25 mmol). Next triazole (2.03 ml_, 35 mmol) and finally (R,R)-(-)-N,N’-dimethyl-1 ,2-cyclohexanediamine ligand (0.56 ml_, 3.5 mmol) were added. The resulting clumpy yellow slurry was stirred until evenly dispersed. Upon heating to 100 oC the reaction mixture changed from a yellow slurry to pale green. As heating progressed the slurry became less thick and was stirred more easily. The light green slurry was stirred for 4 hr at 100 oC and left to stir at room temp overnight. At this point the reaction mixture appeared as a cobalt blue slurry which was then diluted with 20 ml_ ether and 20 ml_ H2O. The resulting solution was thoroughly stirred and transferred to a seperatory funnel then the RBF was subsequently rinsed with 20 ml_ ether and H2O each. The aqueous layer was separated from the organic layer and acidified to pH 1 with 6 ml_ cone. HCI. The now brown/ lime green aqueous layer was extracted twice with EtOAc. The bright yellow organic layers were combined and dried with Na2SO4 and then cone, into a yellow powder under reduced pressure. To the yellow powder was added EtOAc to form a yellow slurry. The solids were filtered off and washed with EtOAc to give a very pale yellow powder, which was found by 1H NMR to be the Intermediate 71 (25% yield). The filtrate was cone, into a yellow solid and purified (FCC, 0-5% MeOH in DCM w/ 0.5% AcOH) to give the title product in a 20% yield. MS (ESI): mass calculated for C9H8N4O2, 204.18; m/z found 205.3 [M+H]+ 1 H NMR (400 MHz, CD3OD): 8.21 – 8.18 (m, 1 H), 7.98 (s, 2H), 7.51 (d, J = 7.9 Hz, 1 H), 2.64 (s, 3H).

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Reference:
Patent; JANSSEN PHARMACEUTICA NV; CHAI, Wenying; LETAVIC, Michael, A.; LY, Kiev, S.; PIPPEL, Daniel, J.; RUDOLPH, Dale, A.; SAPPEY, Kathleen, C.; SAVALL, Brad, M.; SHAH, Chandravadan, R.; SHIREMAN, Brock, T.; SOYODE-JOHNSON, Akinola; STOCKING, Emily, M.; SWANSON, Devin, M.; WO2011/50198; (2011); A1;,
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. 27996-86-7, name is 4-[1,2,4]Triazol-1-yl-benzaldehyde belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4-[1,2,4]Triazol-1-yl-benzaldehyde

A mixture of alpha ionone (1.152 g, 1.23 ml, 6 mmol), 4-(1H-1,2,4-triazol-1-yl) benzaldehydes (0.865 g, 5 mmol), cetyltrimethyl ammonium bromide (0.070 g, 0.5 mmol), sodium hydroxide (0.600 g, 15 mmol) and water (25 ml) was stirred at room temperature for 24 h. Reaction progress was monitored by TLC and compound was extracted with ethyl acetate (2 × 50 ml). The combined organic extract was washed with water (2 × 50 ml), brine solution (50 ml), dried (Na2SO4) and the solvent was removed in vacuum. The crude product was purified by column chromatography (SiO2, 60-120 mesh). Elution with 10 % ethyl acetate in hexane furnished a pale yellow coloured solid (0.400g, 23%). Mp: 108-110OC; IR (KBr, cm-1): 2915, 1651 (C=O), 1598 (C=N); 1H NMR (CDCl3, 300 MHz): delta 0.88 (s, 3H), 0.95 (s, 3H), 1.22-1.29 (m, 1H), 1.43-1.52 (m, 1H), 1.60 (s, 3H), 2.07 (brs, 2H), 2.36 (d, J = 9 Hz, 1H), 5.53 (brs, 1H), 6.39 (d, J = 16 Hz, 1H), 6.85 (dd, J = 16, 9 Hz, 1H), 7.01 (d, J = 16 Hz, 1H), 7.63-7.74 (m, 5H), 8.11 (s, 1H), 8.60 (s, 1H); 13C NMR (CDCl3, 75 MHz): delta 22.92, 23.10, 26.90, 27.95, 31.25, 32.75, 54.67, 2×120.13, 122.83, 125.72, 2×129.72, 130.54, 131.93, 134.81, 137.99, 140.89, 141.16, 149.44, 152.81, 188.53; ESI-MS m/z: 348 [M+1]+; Analysis calculated for C22H25N3O: C, 76.05; H, 7.25; N, 12.09; Found: C, 76.05; H, 7.29; N, 12.03.

If you are hungry for even more, make sure to check my other article about 27996-86-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Suryawanshi; Tiwari, Avinash; Kumar, Santosh; Shivahare, Rahul; Mittal, Monika; Kant, Padam; Gupta, Suman; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 2925 – 2928;,
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. 60166-43-0, name is 1,4-Dimethyl-1H-1,2,3-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. name: 1,4-Dimethyl-1H-1,2,3-triazole

The compound 1G (1.02 g, 1.9 mmol), 1,4-dimethyl-1H-1,2,3-triazole (380 mg, 3.8 mmol) obtained in the previous step,Tetramethylammonium acetate (251mg, 1.9mmol) and PdCl2 (PPh 3) 2 (bistriphenylphosphonium palladium dichloride) (100mg, 0.14mmol) were added to DMF (20mL) and the air was replaced with nitrogen, then protected under nitrogen Then, stir at 100 degrees overnight.After TLC showed that the reaction was over, the reaction was cooled to room temperature, poured into 200 ml of water, and extracted with ethyl acetate (2 × 100 mL).The combined organic phases were washed with a saturated sodium chloride solution (3 × 100 mL), the organic phases were dried over anhydrous sodium sulfate,The desiccant was removed by filtration, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 3: 1 to 1: 1 (volume ratio V: V)),The target product Compound 1H (430 mg, yellow solid) was obtained in a yield of 42%.

If you are hungry for even more, make sure to check my other article about 60166-43-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wuhan Yukeyuan Pharmaceutical Biological Technology Co., Ltd.; Fang Huaxiang; Yu Bin; Li Fangfang; Zhang Xiaolin; Che Peng; Xu Yong; (18 pag.)CN110357878; (2019); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 4928-87-4, 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. 4928-87-4, name is 1,2,4-Triazole-3-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 reaction of 1/7-1, 2, 4-triazole-3 -carboxylic acid (226 mg, 2.0 mmol) and 3,4- dimethoxyaniline (322 mg, 2.1 mmol) in dry DMF (10 mL) was added 1- hydroxybenzotriazole monohydrate (337 mg, 2.2 mmol) and EDC (N-(3- dimethylaminopropyl)-N’-ethylcarbodiimide) (422 mg, 2.2 mmol) followed by N- methylmorpholine (0.88 mL, 8.0 mmol via syringe). The mixture was stirred at room temperature under nitrogen and the solids were gradually dissolved. The contents were stirred at room temperature for 24.0 h, and then slowly diluted into ice cold water and extracted with DCM (50 mL x 2). The DCM phase was washed with cold water (100 mL x 2). The DCM phase was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure and then chromatographed on silica gel using EtOAc as eluent to get the desired amide 1 (60 mg, 12% yield) as a light brown solid. -NMK (400 MHz, DMSO- de): <514.79 (br s, 1H), 10.34 (br s, 1H), 8.58 (br s, 1H), 7.55-7.44 (m, 2H), 6.94-6.93 (m, 1H), 3.76-3.74 (m, 6H) ppm. MH+ = 263.2 m/z. Therefore, this conceptually novel strategy might open impressive avenues to establish green and sustainable chemistry platforms.In my other articles, you can also check out more blogs about 1,2,4-Triazole-3-carboxylic acid. Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF COLORADO, A BODY CORPORATE; NATIONAL JEWISH HEALTH; WEMPE, Michael Fitzpatrick; VAZQUEZ-TORRES, Andres; DAI, Shaodong; (72 pag.)WO2020/41556; (2020); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-36-8, New Advances in Chemical Research in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 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.

Step A: A solution of lH-l,2,3-triazole (1.0 g, 14.5 mmol), methyl iodide (3.1 g, 21.7 mmol) and K2CO3 (4.0 g, 28.9 mmol) in THF (15 mL) was stirred at room temperature for 3 hours. EtOAc (20 mL) and H20 (10 mL) were added, separated. The solvent was concentrated under vacuum. The crude residue was purified by silica gel chromatography eluting with 10% MeOH/DCM to afford l-methyl-lH-l,2,3-triazole (860 mg, 10.4 mmol, 71% yield) as yellow oil.

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Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; YUK, Inn H.; PURKEY, Hans; O’BRIEN, Thomas; WO2015/142903; (2015); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 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. Product Details of 4922-98-9

STEP E; A reaction mixture of compound 35-4 (28.3 mg, 0.1 mmol) and 3-phenyl-1H- 1 ,2,4-triazol-5-amine (16 mg, 0.1 mmol) in ethanol was stirred at 80 0C for overnight. The product was purified using reverse phase HPLC.

I hope this article can help some friends in scientific research. I am very proud of our efforts over the past few months and hope to 5-Phenyl-1H-1,2,4-triazol-3-amine help many people in the next few years.

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

New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 61-82-5, name is 1H-1,2,4-Triazol-5-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C2H4N4

General procedure: A mixture of aldehyde (1.0 mmol), dimedone (1.0 mmol),1H-1,2,4-triazol-3-amine (1.0 mmol) and nano-AlPO4(SO3H) (0.1 g) was stirred in the acetonitrile (4.0 mL)at 50 C for an appropriate time. After the completion of thereaction as indicated by TLC, dichloromethane was addedto the solidified mixture and the insoluble catalyst was separatedby centrifugation. Evaporation of the solvent from thefiltrate and recrystallization of the solid residue from hot ethanolafforded the pure products in good to excellent yields

I hope this article can help some friends in scientific research. 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; Sharghi, Hashem; Aboonajmi, Jasem; Aberi, Mahdi; Shiri, Pezhman; Journal of the Iranian Chemical Society; vol. 15; 5; (2018); p. 1107 – 1118;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 7170-01-6, New Advances in Chemical Research 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. 7170-01-6, name is 3-Methyl-1H-1,2,4-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.

Procedure: A 500 mL round bottom flask was loaded with 4-methoxy-7-chloro-6-azaindole 2e (9.1 g, 50 mmol; dried in vacuo), potassium carbonate (13.8 g, 100 mmol, 2 eq.), copper powder (6.35 g, 100 mmol, 2 eq.), and 3-methyl-1,2,4-triazole (83 g, 1.0 mol, 20 eq.). The solid mixture was heated to melt at 170-175 C. (external oil bath temperature) under a gentle stream of anhydrous nitrogen for 12 h, by which time HPLC analysis indicated that the amount of the peak for the starting material had become 5-30% and the desired product peak becomes about 45% with isomeric by-product peak becomes 15%. As the reaction mixture cooled, MeOH (150 mL) was added slowly to the warm, stirred mixture. Upon cooling, the insoluble material (copper powder) was filtered through a Celite pad, and rinsed with methanol. The filtrate was concentrated in vacuo to a thick paste which was diluted with water (1 L) and extracted with EtOAc (3×150 mL). The EtOAc extracts were dried (MgSO4), filtered and concentrated to obtain about 8 g of crude residue which was crystallized by dissolving in hot CH3CN (50 mL), followed by diluting with water (100 mL) and cooling at 0 C. to collect 1.45 g (12.7%) of the title compound as white solid. The filtrate was purified by C-18 reverse phase silica gel (YMC ODS-A 75 mum) eluted with 15-30% CH3CN/H2O. Appropriate fractions were combined and the aqueous solution after removing CH3CN by rotary evaporator was lyophilized to give additional 1.15 g of the title compound 3-81. The crude aqueous layer was further extracted with EtOAc several times. The ethyl acetate extracts were dried (MgSO4), filtered, concentrated, and crystallized from MeOH to give additional 200 mg of the title compound 3-81. The total yield: 2.8 g (12.2 mmol, Y. 24.5%); MS m/z 230 (MH), HRMS (ESI) m/z calcd for C11H12N5O (M+H), 230.1042, found 230.1038 (Delta-1.7 ppm); 1H NMR (CDCl3) delta ppm 2.54 (3H, s, CH3), 4.05 (3H, s, OCH3), 6.73 (1H, s, H-3), 7.40 (1H, s, H-2), 7.56 (1H, s, H-5), 9.15 (1H, s, triazole-H-5); 13C NMR (CDCl3, 125.7 MHz) 8 ppm 14.2 (triazole-Me), 56.3 (OMe), 100.5 (C-3), 116.9 (C-5), 123.5, 127.2, 127.5 (C-2), 129.5 (C-7), 141.2 (C-5′), 149.5 (C-4), 161.8 (C-3′); Anal. Calcd for C11H11N5O: C 57.63; H 4.83; N 30.55, found C, 57.37, H, 4.64, N, 30.68. The structure was confirmed by a single X-ray crystallographic analysis using crystals obtained from C-18 column fractions. A portion of C-18 column fractions containing a mixture of the desired 3-methyl-1,2,4-triazolyl analog 3-81 and isomeric 5-methyl-1,2,4-triazolyl analog 4-81 was further purified by C-18 reverse phase column eluting with 8-10% CH3CN/H2O. Appropriate fractions were extracted with CH2Cl2, and slow evaporation of the solvent gave crystalline material of the isomeric 7-(5-methyl-1,2,4-triazolyl)-4-methoxy-6-azaindole (4-81): MS m/z 230 (MH), 1H NMR (CDCl3) delta ppm 3.05 (3H, s, CH3), 4.07 (3H, s, OCH3), 6.74 (1H, q, J=2.4, H-2), 7.37 (1H, t, J=2.4, H-3), 7.65 (1H, s, H-5), 8.07 (1H, s, triazole-H-3). The structure was confirmed by a single X-ray crystallographic analysis.

I am very proud of our efforts over the past few months and hope to 3-Methyl-1H-1,2,4-triazole help many people in the next few years.

Reference:
Patent; Ueda, Yasutsugu; Connolly, Timothy P.; Kadow, John F.; Meanwell, Nicholas A.; Wang, Tao; Chen, Chung-Pin H.; Yeung, Kap-Sun; Zhang, Zhongxing; Leahy, David Kenneth; Pack, Shawn K.; Soundararajan, Nachimuthu; Sirard, Pierre; Levesque, Kathia; Thoraval, Dominique; US2005/209246; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 584-13-4, name is 4H-1,2,4-Triazol-4-amine belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 4H-1,2,4-Triazol-4-amine

General procedure: 4-Amino-1,2,4-triazole (0.005 mol) was taken in 150 mL beaker and dissolved in ethanol (10 mL). Equimolar amount of substituted benzaldehyde was added to the ethanolic solution. Then, 0.5 mL of glacial acetic acid was added dropwise to the reaction mixture and stirred with glass rod. The contents were irradiated in MW at 360W for required time with continuous monitoring by TLC. Then the reaction mixture was filtered. Crude product was recrystallized from ethanol to obtain pure compound. Same procedure was repeated but with different amount of catalysts, i.e., 0.75 mL and 1 mL. The progress of reaction was monitored by TLC after 10 s interval. On completion of reaction, resultant mass was filtered and recrystallized from ethanol. The same procedure was used for the synthesis of rest of the compounds. The work was continued by using different amounts of lemon juice as catalyst at 360 W for required time. 4-((4H-1,2,4-triazol-4-ylimino)methyl)phenol (I) IR (numax, KBr, cm-1): 3378 (O-H str.), 3107 (aromatic -C-H str.), 1665 (C=N str.), 1590 (N-N str.), 1607, 1567, 1507, 1475 (C=C str.), 1311 (O-H bending), 1275 (C-N str.), 1168 (C-O), 861 (C-N bending), 755 (C-H bending), and 771/cm (C=C bending); 1H NMR (DMSO-d6, 400 MHz, delta): delta 10.23 (s, 1H, OH), 8.98 (s, 2H, -CH=), 8.91 (s, IH, -CH=N-), 7.71-6.89 (m, 4H, Ar-H); 13C NMR (DMSO-d6, 100 MHz, delta): delta 159.3, 157.4, 148, 131.67, 126.13, 116.89; Analysis calculated for C9H8N4: C, 57.44; H, 4.25; N, 29.78. Found: C, 57.45; H, 4.26; N, 29.79.

If you are hungry for even more, make sure to check my other article about 584-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mhaske, Sadhana D.; Takate, Sushama J.; Dhawale, Rhushikesh N.; Akolkar, Hemantkumar N.; Randhavane, Pratibha V.; Karale, Bhausaheb K.; Indian Journal of Heterocyclic Chemistry; vol. 27; 1; (2017); p. 89 – 97;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

New discoveries in chemical research and development in 2021. The transformation of simple hydrocarbons into more complex and valuable products via catalytic C–H bond functionalisation has revolutionised modern synthetic chemistry. 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. 7411-23-6

N-chloroethylmorpholine hydrochloride (197 mg, 1.32 mmol), 3,5-dibromo-1H-1,2,4-triazole (250 mg, 1.1 mmol) and potassium carbonate (456 mg, 3.3mmol) were added to DMF (5 mL) in a 25 mL round bottom flask. The reaction was then stirred at 50 C under nitrogen. The solvent was removed in vacuo, water was added, and the product extracted with DCM (3 ×). The organic phase was dried over a phase separator and the solvent removed in vacuo. The product was purified by silica column chromatography eluting with 0-10% MeOH in DCM to yield [4-[2-(3,5-dibromo-1,2,4-triazol-1-yl)ethyl]morpholine (374 mg, 1.1 mmol, 99% yield) ]. UPLC-MS (ES+, Method A), 0.65 min, m/z 341.0 [M+H]+

We’ll also look at important developments in the pharmaceutical industry because understanding organic chemistry is important in understanding health, medicine, the role of 3,5-Dibromo-1H-1,2,4-triazole ,and how the biochemistry of the body works.

Reference:
Patent; REDX PHARMA PLC; JONES, Clifford, D.; BUNYARD, Peter; PITT, Gary; BYRNE, Liam; PESNOT, Thomas; GUISOT, Nicolas, E.S.; (318 pag.)WO2019/145729; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics