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. 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 3-Methyl-1H-1,2,4-triazole

A mixture of tris(dibenzylideneacetone)dipalladium(0) (98%, 94.7 mg, 0.101 mmol) and di-tert-butyl[3,4,5,6-tetramethyl-2?,4?,6?-tri(propan-2-yl)biphenyl-2-yl]phosphane (95%, 103 mg, 0.203 mmol) in toluene (10 mL) was degassed with nitrogen for 5 minutes, then heated at 125 C. for 3 minutes. In a separate flask, a mixture of C43 (1.70 g, 3.38 mmol), 3-methyl-1H-1,2,4-triazole (561 mg, 6.75 mmol), and potassium phosphate (1.48 g, 6.97 mmol) in toluene (10 mL) and 1,4-dioxane (10 mL) was degassed with nitrogen for 10 minutes. The catalyst solution was transferred to the reaction flask via syringe, and the reaction mixture was heated at 125 C. for 2 hours, whereupon it was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo; silica gel chromatography (Gradient: 50% to 100% ethyl acetate in heptane) provided the product as an off-white solid. Yield: 1.3 g, 2.6 mmol, 77%. LCMS m/z 506.4 [M+H]+. 1H NMR (400 MHz, CDCl3), characteristic peaks: delta 9.52 (br s, 1H), 8.21 (d, J=7.9 Hz, 1H), 7.38 (d, J=7.8 Hz, 1H), 7.25-7.31 (m, 1H, assumed; partially obscured by solvent peak), 6.68 (d, J=10.0 Hz, 1H), 5.05 (d, J=15.2 Hz, 1H), 4.20-4.32 (m, 2H), 3.53-3.62 (m, 1H), 3.14 (d, J=15.2 Hz, 1H), 2.49 (s, 3H), 1.84 (s, 3H), 1.00 (d, J=6.6 Hz, 1H), 0.69 (d, J=6.5 Hz, 1H).

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 7170-01-6.

Reference:
Patent; Pfizer Inc.; Pettersson, Martin Youngjin; am Ende, Christopher William; Johnson, Douglas Scott; Kauffman, Gregory Wayne; Stepan, Antonia Friederike; Verhoest, Patrick Robert; (64 pag.)US2016/222007; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, belongs to triazoles compound, 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 16681-65-5, Safety of 1-Methyl-1H-1,2,3-triazole

Intermediate 18: 1-Methyl-1H-1,2,3-triazole-5-carbaldehydeThe title compound was prepared according to the patent application WO2008/135826. To a 50 mL 2-necked flask containing 1-methyl-1H-1,2,3-triazole (1.0 g, 12.0 mmol, prepared according to PCT Int. AppL 2008098104) was added THF (45 mL) and the colorless solution was cooled to -40 C. Then, n-BuLi (2.5 M in hexanes, 4.8 mL, 12.0 mmol) was added dropwise which afforded a dark reddish-brown viscous solution. The mixture was stirred between -30 to -20 C for 45 minutes, then neat DMF (3 mL, 38,5 mmol) was introduced at -10 C. The mixture was allowed to warm up to room temperature and stirred for 60 minutes, followed by pouring into water. The aqueous portion was extracted with EtOAc (4 x 50 mL) and the combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The aqueous portion was back- extracted with DCM (3 x 50 mL) and dried as above. The combined organics were concentrated to give a light brown oil that was much more UV active than the starting material, TLC in either 25% CH3CN-DCM or 25% EtOAc-DCM showed the product to have a slightly higher Rf than the starting material. Chromatography on silica gel (100% DCM increasing to 25% CH3CN-DCM) provided the title compound as a colorless oil.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

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.; WO2015/57206; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, molecular formula is C2HBr2N3, 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. Formula: C2HBr2N3

A solution of 1.4 g (36 mmol) of sodium hydroxide in13 mL of water was added to a solution of 8.0 g (36 mmol) of 3,5-dibromo-1H-1,2,4-triazole (1) in100 mL of acetone. The two-phase system thus formed was stirred at 20 C until it became homogeneous, and 4.6 g (36 mmol) of dimethyl sulfate was added dropwise at such a rate that the temperature of the mixture did not exceed 40 C. The mixture was then refluxed for 2 h. The reaction was assumed to be complete when the mixture became weakly acidic and sodium methyl sulfate precipitated. The mixture was filtered,and the solvent was distilled off from the filtrate under reduced pressure. The residue was washed with water, and the precipitate was filtered off and recrystallized from hexane. Yield 7.8 g (88 %), mp 64-65 C [22]. IR spectrum, nu, cm-1: 2951, 1717, 1699, 1464, 1418,1391, 1354, 1275, 1250, 1115, 1016, 989, 712, 700. 1H NMR spectrum, delta, ppm: 3.87 s (3H, CH3). 13C NMR spectrum, deltaC, ppm: 37.4 (CH3), 131.3 (C3),139.1 (C5). Mass spectrum, m/z (Irel, %): 243 (51.1) [M]+, 241 (100) [M]+, 239 (48.9) [M]+, 229 (21.3), 227 (48.3), 225 (24.2), 218 (1.2), 200 (6.1), 198 (12.3), 196 (5.1), 162 (14.5), 160 (13.1), 136 (33.4), 134 (34.9), 122 (30.6), 120 (31.3), 119 (6.3), 117 (7.4), 108 (14.6), 107 (7.7), 106 (16.2), 105 (8.9), 93 (15.9), 91 (18.9), 81 (40.9), 79 (32.5), 52 (12.7), 43 (33.8), 41 (12.2), 40 (13.3), 39 (9.1), 38 (18.5), 29 (53.2), 28 (10.7), 27(16.3), 26 (8.2), 15 (60.3), 12 (7.4).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7411-23-6, its application will become more common.

Reference:
Article; Tolstyakov; Russian Journal of Organic Chemistry; vol. 54; 10; (2018); p. 1537 – 1547; Zh. Org. Khim.; vol. 54; 10; (2018); p. 1525 – 1534,10;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 288-88-0, name is 1H-1,2,4-Triazole, belongs to triazoles compound, 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 288-88-0, Safety of 1H-1,2,4-Triazole

To a solution (3 ML) of 1,2,4-triazole (0.259 g, 3.75 mmol) in N,N-dimethylformamide was added small portions of sodium hydride (60% dispersion in oil, 0.12 g, 3.0 mmol) at about 20 C., and the mixture was stirred for about 3 hr until hydrogen was not generated.To a solution of sodium salt of 1,2,4-triazole thus obtained was added dropwise a solution (5.5 ML) of the total amount of (2R,3R)-3-(2′,4′-difluorophenyl)-3,4-epoxy-2-methanesulfonyoxybutane obtained above in N,N-dimethylformamide at room temperature.The mixture was stirred at 75-80 C. for 1.5 hr.The reaction mixture was added dropwise to water (20 ML), and the mixture was extracted 3 times with ethyl acetate (20 ML).The extracted ethyl acetate layers were mixed, and the mixture was washed twice with saturated brine (10 ML) and dried over anhydrous magnesium sulfate.After filtration, the filtrate (ethyl acetate solution) was concentrated and the obtained concentrate was subjected to silica gel column chromatography (SiO2, 5 g) and eluted with n-heptane-ethyl acetate (10:1)ethyl acetate.The objective fraction was concentrated to give a pale-yellow oil (0.297 g).The obtained pale-yellow oil was crystallized from a mixed solvent of ethyl acetate (1 ML)-n-heptane (4 ML) to give the title compound (0.185 g, yield from (2R)-2′,4′-difluoro-2-hydroxypropiophenone: 44%).As a result of analysis by HPLC, the optical purity was 100% e.e.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Sumika Fine Chemicals Co., Ltd.; US2003/236419; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 1455-77-2, A common heterocyclic compound, 1455-77-2, name is 3,5-Diamino-1,2,4-triazole, molecular formula is C2H5N5, 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.

Included at room temperature3,5-diamino-1,2,4-triazole 15.0 g (0.151 mol)And dehydrated N,N-dimethylformamide 100mLAdd 28percent to the suspensionSodium methoxide methanol solution 29.2g (0.151mol)After making a uniform solution and stirring for 30 minutes,30.1 g (0.151 mol) of 3-chloropropyltrimethoxydecane was added.Stir at 77~80 ¡ã C for 4 hours.After cooling the suspension reaction solution to 3 ¡ã C,Filter out insoluble matter,And the solvent of the filtrate is distilled off under reduced pressure,Obtained 35.7 g (0.137 mol, brown viscous,Yield 90.5percent).

The synthetic route of 1455-77-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHIKOKU CHEMICALS CORPORATION; MURAI,, TAKAYUKI; TANIOKA, MIYA; IIDA, SHUSAKU; KATSUMURA, MASATO; YAMAJI, NORIAKI; IMAMINE, TAKAHITO; TSUJINO, MASAHIKO; HIRAO, HIROHIKO; (52 pag.)TW2018/41929; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 956317-36-5, 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 956317-36-5 as follows.

A round-bottom flask equipped with a magnetic stirrer bar was charged with CH2C12(70 mL) and 5-methyl-2-(2H-1,2,3-triazole-2-yl)benzoic acid (2.Og, 9.4 mmol, 1 equiv).To the clear solution, pentafluoro phenol (1.72 g, 9.4 mmol, 1 equiv) and EDChydrochloride (1.79 g, 9.4 mmol, 1 equiv) were successively added. After addition ofDMAP (0.23 g, 1.9 mmol, 0.2 equiv), the clear solution was stirred at room temperature for 2 h. The reaction mixture was evaporated to dryness under reduced pressure and purified by column chromatography (Si02, cyclohexane/ethyl acetate 9: 1), yielding perfluorophenyl 5-methyl-2-(2H-1,2,3-triazole-2-yl)benzoate (2.5 g, 72 %) as a colorlesspowder.?H NMR (500 MHz, CDC13) oe = 7.83 (s, 2H), 7.78 (d, J = 8.20 Hz, 1H), 7.76 (d, J = 1.40, 1H), 7.54 (dd, J = 1.40, 8.25 Hz, 1H), 2.51 (s, 3H)?3C NMR (125 MHz, CDC13) oe = 162.8, 139.2, 136.6, 136.1, 134.0, 131.1, 124.6, 123.6, 21.1 (CM omitted due to low intensity)?9F NMR (470 MHz, CDC13) oe = -151.2 (m), -157.8 (t, J = 21.7 Hz), -162.3 (m)

According to the analysis of related databases, 956317-36-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANDOZ AG; HOeFERL-PRANTZ, Kathrin; BARTH, Roland; RICHTER, Frank; ZUPANCIC, Borut; (126 pag.)WO2016/20403; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Application of 7170-01-6, 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. 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.

((2S,3S)-3-(((benzyloxy)carbonyl)amino)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-2-yl)methyl methanesulfonate (3.74 g, 8.0 mmol), 3-methyl-1H-1,2,4-triazole (2.00 g, 24.0 mmol), K2CO3 (6.64 g, 48.0 mmol) and NaI (2.88 g, 17.2 mmol) were slurried in DMF (16 mL) and heated to 70 C. with stirring. After 24 h the mixture was concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 2%) to afford title compounds (1.64 g, 44% combined) as an off-white solid (unseperable mixture). LCMS: m/z=466.2 (M+1).

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

Reference:
Patent; NOVARTIS AG; AULAKH, Virender Singh; CASAREZ, Anthony; LIN, Xiaodong; LINDVALL, Mika; MCENROE, Glenn; MOSER, Heinz Ernst; RECK, Folkert; TJANDRA, Meiliana; SIMMONS, Robert Lowell; YIFRU, Aregahegn; ZHU, Qingming; US2015/266867; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 4928-87-4, A common heterocyclic compound, 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, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Single crystals of 1 were prepared by a branched tube method [13], 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 3 days, colorless crystals were deposited in the cooler arm which were filtered off, washed with water and air dried. (0.225 g, yield 54%), m.p. ?195 C. (Found C 8.55, H 0.99, N 10.43%. calculated for C3H4BrN3O3Pb; C 8.63, H 0.96, N 10.07%). IR (cm-1) selected bands: 464 (s), 651 (s), 1100 (s), 1303 (m), 1370 (m), 1457 (vs), 1606 (s) and 3370 (br).

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; Joo, Sang Woo; Ultrasonics Sonochemistry; vol. 20; 5; (2013); p. 1254 – 1260;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 7170-01-6, 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. 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.

EXAMPLE 8 In a sealed tube dicarbonyl intermediate 10 (50 mg, 0.13 mmol), 3-methyl-1,2,4-triazole (52 mg, 0.75 mmol) and copper powder (16 mg, 0.25 mmol) were combined and heated at 140 C. with microwaves for 1 h. The reaction was diluted with MeOH (3 mL), filtered through celite and the filtrate was purified by preparative HPLC to yield 16 (3 mg, 0.007 mmol, 5%) as a yellow solid. 1H NMR: (500 MHz, CD3OD) delta 8.97 (s, 1H), 8.61 (s, 1H), 8.28 (s, 1H), 8.27 (s, 1H), 7.52-7.40 (m, 5H), 4.02-3.44 (m, 8H); LC/MS: (ES+) m/z (M+H)+=431; HPLC Rt=0.82 min., column G, conditions B.

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

Reference:
Patent; Bender, John A.; Yang, Zhong; Kadow, John F.; Meanwell, Nicholas A.; US2005/124623; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 7411-23-6, name is 3,5-Dibromo-1H-1,2,4-triazole, A new synthetic method of this compound is introduced below., Quality Control of 3,5-Dibromo-1H-1,2,4-triazole

In a 50 mL round bottomed flask, 3,5-dibromo-1H-1,2,4-triazole (Int-1, 1.50 g, 6.61 mmol) was dissolved in DMF (15 mL) and the solution was cooled to 0-5 C (ice bath). Sodium hydride (55% dispersion in mineral oil, 317 mg, 7.93 mmol) was added in portions and the resulting mixture was stirred for 30 min at 0-5 C and for 15 min at room temperature. After that, 1- fluoro-2-iodoethane (1.15 g, 537 mu, 6.61 mmol) was added dropwise at room temperature. The resulting mixture was stirred for 18 h at room temperature. After that, it was concentrated in vacuo, the residue was purified by column chromatography (silica gel, 70 g, eluting with ethyl acetate / n-heptane, gradient 0: 100 to 40:60 v/v) to yield the title compound as yellow oil (1.51 g, 84%). 1H NMR (CDCl3, 300 MHz): delta 4.46 (td, J = 4.7, 24.2 Hz, 2 H), 4.80 (td, J = 4.7, 46.3 Hz, 2 H). MS (ES+) m/z 271.9, 273.9, 275.9 [M+H, 2 Br isotopes].

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BARTELS, Bjoern; BERCHTOLD, Stefan; GALLEY, Guido; GOERGLER, Annick; JAKOB-ROETNE, Roland; KRUMMENACHER, Daniela; LIMBERG, Anja; NEIDHART, Werner; RATNI, Hasane; REUTLINGER, Michael; RODRIGUEZ SARMIENTO, Rosa Maria; SCHNIDER, Christian; (309 pag.)WO2018/87018; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics