Category: Triazoles

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. 135242-93-2, name is (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C4H7N3O

c 3-Chloromethyl-1-methyl-1H-1,2,4-triazole (1-Methyl-1H-1,2,4-triazol-3-yl)methanol (500 mg, 4.4 mmol) (prepared using the conditions described in EP-A-421210) was added portionwise to thionyl chloride (5 ml) at 0 C. Upon complete addition the mixture was allowed to warm to room temperature, then heated at reflux for 45 minutes (gas evolution observed). Upon cooling the thionyl chloride was removed in vacuo. The residue was partitioned between dichloromethane and aqueous sodium hydrogen carbonate. The aqueous phase was further extracted with dichloromethane (x2). The combined extracts were dried (Na2SO4), filtered and evaporated to give the title chloride (570 mg), as an oil. This material was used without further purification. Data for the title compound: 1H NMR (250 MHz, CDCl3) delta 3.92 (3H, s), 4.63 (2H, s), 8.10 (1H, s). MS (ES+) m/e 133 [MH]+, 131 [MH]+.

We’ll also look at important developments in the pharmaceutical industry because understanding organic chemistry is important in understanding health, medicine, the role of (1-Methyl-1H-[1,2,4]triazol-3-yl)methanol ,and how the biochemistry of the body works.

Reference:
Patent; Merck Sharp & Dohme Ltd.; US6355798; (2002); B1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 23579-79-5, 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. 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, molecular formula is C3H3Br2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

Intermediate 3 3-Bromo-/V-(cyclopropylmethyl)-l-methyl-lH-l,2,4-triazol-5-amine To a solution of 3,5-dibromo-l-methyl-l/-/-l,2,4-triazole (0.700 g, 2.90 mmol) and cyclopropanemethylamine (0.50 mL, 5.8 mmol) in 1,4-dioxane (2.5 mL) and DMA (1 mL) was added Lambda/,/V-diisopropylethylamine (0.47 mL, 5.8 mmol). The mixture was heated at 130C in a sealed tube for 16 h and then cooled down to rt. Water (5 mL) was added and the resulting solution was extracted with EtOAc (3 x 15 mL). The combined organic layers were washed with water (10 mL) and brine (10 mL), dried over sodium sulfate and concentrated. The residue was triturated with MTBE to give the title compound as a solid (0.330 g, 49%). XH NMR (400 MHz, CDCI3): delta ppm 0.23 – 0.27 (m, 2 H), 0.53 – 0.58 (m, 2 H), 1.05 – 1.16 (m, 1 H), 3.23 (dd, 2 H), 3.56 (s, 3 H), 3.97 (br s, 1 H).

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 3,5-Dibromo-1-methyl-1H-1,2,4-triazole is helpful to your research.

Reference:
Patent; ACTURUM LIFE SCIENCE AB; BESIDSKI, Yevgeni; YNGVE, Ulrika; PAULSEN, Kim; LINDE, Christian; MALMBORG, Jonas; WO2014/195322; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 7411-23-6, New Advances in Chemical Research 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, molecular formula is C2HBr2N3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

A mixture of salt 1a (1 g, 2.9 mmol), 3,5-dibromo-1,2,4-triazole (0.66 g, 2.9 mmol), and K2CO3 (1.20 g, 8.7 mmol) in DMF (10 ml) was refluxed for 2 h. The mixture was cooled and poured into water (50 ml). The precipitate formed was filtered off and recrystallized from DMF. Yield 0.56 g (64%), colorless crystals; mp 244-246 C. IR spectrum, nu, cm-1: 3078, 3059, 3040 (H arom), 2932 (H2), 1628, 1558, 1531, 1512, 1466, 1439, 1404, 1292, 1265, 1215, 1173, 1157, 1142, 1068, 987, 972, 818, 768, 748, 717. 1H NMR spectrum (DMSO-d6), delta, ppm: 5.61 (2H, s, CH2); 7.35 (1, d, J = 9.2, H Ar); 7.51 (1, dd, J = 8.2, J = 0.9, H Ar); 7.61 (1, dd, J = 8.2, J = 1.4, H Ar); 7.76 (1H, d, J = 8.2, H Ar); 7.90-7.93 (2, m, H Ar). 13C NMR spectrum (DMSO-d6), delta, ppm: 45.1 (CH2); 108.5 (C); 117.1 (CH); 122.8 (CH); 126.3 (CH); 128.3 (CH); 128.9 (CH); 129.8 (C); 130.7 (CH); 130.8 (C); 137.5 (C); 145.4 (C); 153.37 (C). Found, %: 51.78; 2.57; N 14.03. C13H8BrN3O. Calculated, %: C 51.68; H 2.67; N 13.91.

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

Reference:
Article; Osyanin; Osipov; Klimochkin, Yu. N.; Chemistry of Heterocyclic Compounds; vol. 47; 12; (2012); p. 1607 – 1609; Khim. Geterotsikl. Soedin.; vol. 47; 12; (2011); p. 1914 – 1916,3;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 151899-62-6, name is 3-Iodo-1-trityl-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. category: Triazoles

Nitrogen gas was bubbled through a solution of 3-iodo-l-trityl-lH-l,2,4-triazole (37.3g, 85.35mmol), and triethylamine (17.8ml, 128mmol) in anhydrous DMF (300ml) heated at 350C for 30 mins. Pd(PPh3)2Cl2 (2Ag, 3.4mmol) and CuI (651mg, 3.4mmol) were added followed by addition of ethynyltrimethylsilane (18ml, 128mmol) in anhydrous DMF (18ml) over 5 15 hours via syringe pump. After complete addition the mixture was heated at 350C for a further 5 hours. The mixture was poured into water (700ml) and extracted with EtOAc (3 x 300ml). Combined EtOAc layers washed with water (2 x 500ml), sat. NaCl (250ml), dried over Na2SO4, filtered and evaporated. The residue was purified by MPLC on silica gel eluting with a gradient from 100% hexanes to 10% EtOAc in hexanes to afford the title compound. 1HNMR (500 MHz, 10 CDCl3) delta: 7.96 (s, IH), 7.37 (m, 9H), 7.14 (m, 6H), 0.27 (s, 9H).

The catalyzed pathway has a lower Ea, but the net change in energy that results from the reaction is not affected by the presence of a catalyst. In my other articles, you can also check out more blogs about 151899-62-6

Reference:
Patent; MERCK & CO., INC.; WO2008/57336; (2008); A2;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Research speed reading in 2021. Redox catalysis has been broadly utilized in electrochemical synthesis due to its kinetic advantages over direct electrolysis. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C3H5N3

General procedure: TBHP (3 eq.) was added to a solution of 3-phenyl-1,2,4-triazole (0.4 mmol) 1a, benzaldehyde 2a (0.6 mmol), followed by TBAI (20 mol%) in DCE(4 mL). The reaction mixture was stirred at 120 oC under nitrogen atmosphere for 5 h. After completion of the reaction confirmed by TLC, the reaction mixture was cooled to room temperature and partitioned between water and ethyl acetate. The organic and aqueous layers were then separated and aqueous layer was extracted with ethyl acetate twice. The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude. The crude was further purified by silica gel chromatography using EtOAc/hexane as eluents to furnish the desired product 3 or 5.

Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law. In my other articles, you can also check out more blogs about 7170-01-6, and we look forward to future research findings.

Reference:
Article; Agisho, Habtamu Abebe; Esatu, Habdolo; Hairat, Suboot; Zaki, Mehvash; Tetrahedron Letters; (2020);,
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. 6818-99-1, name is 3-Chloro-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. 6818-99-1

A solution 2-(5-bromo-3-ethylsu lfanyl-2-pyridyl)-5-cyclopropyl-3-methyl-6-(trifluoromethyl)im idazo[4 , 5- c]pyridin-4-one A4 (Prepared as described before, 150 mg, 0.3169 mmol) in N,N-dimethylformamide (0.3169 mL)was added 3-chloro-1H-1,2,4-triazole (36.09 mg, 0.3486 mmol), (1R,2R)-N1,N2-dimethylcyclohexane-1,2-diamine (2.822 mg, 0.00341 mL, 0.03169 mmol), potassium carbonate (8.760 mg, 0.064 mmol) and copper(l) iodide (3.018 mg, 0.01585 mmol). The reaction mixture was stirred at reflux overnight. Same quantity of N,N-dimethylethylenediamine, copper(l) iodide and potassium carbonate were added at the mixture and the mixture was stirred at 120C overnight The reaction mixture was filtered through an Hyflo pad, which was rinsed with methanol, then the reactionmixture was concentrated under vacuum. The residue was subjected to column chromatography over silica gel, eluting with ethyl acetate I cyclohexane. The selected fractions were evaporated to yield the title compound (30% yield). LC-MS(Method A): RT 1.08, 476 (M+H).

If you are hungry for even more, make sure to check my other article about 6818-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; JUNG, Pierre, Joseph, Marcel; EDMUNDS, Andrew; MUEHLEBACH, Michel; HALL, Roger, Graham; (106 pag.)WO2017/89190; (2017); A1;,
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. 1455-77-2, name is 3,5-Diamino-1,2,4-triazole belongs to triazoles compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C2H5N5

Example 243: Preparation of 6-((4-((3-amino-lH-l,2,4-triazol-5-yl)amino)-5-(trifluoro methyl)pyrimidin-2-yI)amino)-3,4-dihydroquinolin-2(lH)-one6-((4-Chloro-5-(trifluoromethyl)pyrimidin-2-yl)amino)-3,4-dihydroquinolin-2(lH)-one (0.072 g, 0.210 mmol), lH-l ,2,4-triazole-3,5-diamine (0.021 g, 0.210 mmol) and -ethyl-N- isopropylpropan-2-amine (0.037 ml, 0.210 mmol) were mixed in DMF (2 ml). The mixture was microwaved at 1 10 °C for 20 min. Added copper (6.68 mg, 0.105 mmol) and more base and the mixture was microwaved at 130 °C for 20 min and then concentrated. 7 mg of product was recovered after automated reverse phase chromatography (water-3percent DMF in MeCN eluent). MS calcd for [C16Hi4F3N90+H]+: 406.14, found 406.10.

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-Diamino-1,2,4-triazole, in my other articles.

Reference:
Patent; SALK INSTITUTE FOR BIOLOGICAL STUDIES; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; YALE UNIVERSITY; SHAW, Reuben J.; EGAN, Daniel F.; COSFORD, Nicholas; TURK, Benjamin; VAMOS, Mitchell; PANICKAR, Dhanya Raveendra; CHUN, Matthew; SHEFFLER, Doug; (315 pag.)WO2016/33100; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 16681-70-2, 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, 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.

[0742] To a solution of Compound 1 (15.9 mg, 30 f.tmol) indioxane (0.3 mL) was added HCI (149 f.LL, 598 fllllOI). Theresulting solution was stirred at room temperature for 2 hours,and then concentrated in vacuo. In a separate flask, a solutionof 3H-[1,2,3]triazole-4-carboxylic acid (4.1 mg, 36 f.tmol)and HATU (14 mg, 36 f.tmol) in DMF (0.3 mL) was stirred atroom temperature for 30 minutes. After this time, a solution ofthe crude amine in DMF (0.3 mL) was added, followed byDIPEA (16 f.LL, 90 f.tmol). The resulting solution was stirredfor 1 hour at room temperature then concentrated in vacuowhen the reaction was deemed complete by LCMS to yieldCompound 2 (16 mg), which was used without further purification.

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

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; Fleury, Melissa; Beausoliel, Anne-Marie; Hughes, Adam D.; Long, Daniel D.; Wilton, Donna A.A.; US2015/210690; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 1001401-62-2, 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, 1001401-62-2, name is 2-(2H-1,2,3-Triazol-2-yl)benzoic acid, molecular formula is C9H7N3O2, 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 (R)-3-(3-iodo-benzyl)-morpholine B-5 (100 mg, 0.33 mmol) and DIPEA (57 muL, 0.33 mmol) in DMF (1.5 mL) was added to a RT solution of 2-(2H-1,2,3-triazol-2-yl)benzoic acid E-2 (62 mg, 0.33 mmol), TBTU (111 mg, 0.35 mmol) and DIPEA (57 muL, 0.33 mmol) in DMF (1.5 ml) under argon and the resulting mixture was stirred for 22 h. The reaction mixture was quenched with sat. aq. NaHCO3 and stirred for 10 min before being diluted with water and extracted with DCM (3×). The combined organic extracts were washed with 2M aq. NaOH (1×), 2M aq. HCl (1×) and brine (1×), dried over Na2SO4, filtered and evaporated in vacuo. The crude product was purified by prep. HPLC (method F) to give the title compound as a white solid. LC-MS D: tR=0.93 min; [M+H]+=474.91

In the meantime we’ve collected together some recent articles in this area about 2-(2H-1,2,3-Triazol-2-yl)benzoic acid to whet your appetite. Happy reading!

Reference:
Patent; ACTELION PHARMACEUTICALS LTD.; Bolli, Martin; Boss, Christoph; Brotschi, Christine; Heidmann, Bibia; Sifferlen, Thierry; Williams, Jodi T.; US2015/158855; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 41253-21-8, 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, 41253-21-8, name is Sodium 1,2,4-triazol-1-ide, molecular formula is C2H2N3Na, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, below Introduce a new synthetic route.

A suspension of 2-fluorobenzylnitrile (3.0 g, 25 mmol) and 1,2,4-triazole sodium salt (2.4 g, 27 mmol) were stirred in tetrahydrofuran (7 mL) and dimethylformamide (14 mL) at 95 C. for 18 h. After cooling and concentrating, the product was crystallized from hot CH2Cl2/hexane (1:1) to give the title compound as a white solid (4.25 g, 100% yield). 1H-NMR (300 MHz, CDCl3) delta ppm: 8.74 (1H, s), 8.16 (1H, s), 7.82 (1H, dd, J=4.9,1.3 Hz), 7.77-7.25 (2H, m), 7.57-7.51 (1H, m). LCMS [M+H]+ calcd for C9H7N4: 171.06; found: 171.12.

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 Sodium 1,2,4-triazol-1-ide is helpful to your research.

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