Tag: M.W=0-100

584-13-4, 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 584-13-4 as follows.

General procedure: Synthesis of triazole Schiff?s bases was reportedpreviously [44]. Briefly, 4-arylimino-1,2,4-triazoles (1-14)and 3-arylimino-1,2,4-triazoles (15-23) were synthesized byrefluxing 4-amino-1,2,4-triazoles, or 3-amino-1,2,4-triazoles(2 mM) with equimolar amounts of substituted benzaldehydeand H2SO4 (2 mL) in ethanol (15 mL) for 4-10 h. Reactionprogress was monitored by TLC under UV light at 254 and365 nm or via exposure to iodine vapours. After completionof reaction, the solvent was vaporised under reducedpressure on a rotary evaporator. Resulting compounds werewashed with hexane and crystallized from ethanol to obtain apure compounds.

According to the analysis of related databases, 4H-1,2,4-Triazol-4-amine, the application of this compound in the production field has become more and more popular.

Reference:
Article; Choudhary, Muhammad I.; Imad, Rehan; Khan, Khalid M.; Naqeeb, Uzma; Shaikh, Muniza; Siddiqui, Salman; Subzwari, Fakiha; Zafar, Humaira; Medicinal Chemistry; vol. 16; 4; (2020); p. 575 – 591;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

A common heterocyclic compound, 288-88-0, name is 1H-1,2,4-Triazole, molecular formula is C2H3N3, 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. 288-88-0.

A flask was charged with K2CO3 (12.1689 g, 88 mmol), 1H-1,2,4-triazole (2.0042 g, 29 mmol), Cu2O(430 mg, 3 mmol) and 1,10-phenanthroline (1.0452 g, 5.8 mmol) and then evacuated and back-filled with N2. Then, anhydrous DMF (20 ml) and iodobenzene (8.9764 g, 4.92 ml, 44 mmol) were added and the resulting mixture was heated to 120 C for 64 h and then diluted with CH2Cl2 (40 ml). The mixture was filtered through a pad of Celite and the residue washed with CH2Cl2 (20 ml). The resulting organic layer was washed with water (20 ml) and brine (20 ml), dried over MgSO4 and concentrated under reduced pressure. The crude mixture was purified by column chromatography (cyclohexane/ethyl acetate 8/0?2/0) to yield the product as a pale yellow solid (2.986 g, 71%).

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

Reference:
Article; Paul, Susann; Schweizer, W. Bernd; Rugg, Graham; Senn, Hans Martin; Gilmour, Ryan; Tetrahedron; vol. 69; 27-28; (2013); p. 5647 – 5659;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, I believe this compound will play a more active role in future production and life. 7170-01-6

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 81-84. 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) ? 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. 1HNMR 400 MHz (CDCl3) ? 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) ? 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) ? ppm: 2.69 (3H, s, CH3), 7.49-7.55 (2H, m, 2xCH), 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.

The chemical industry reduces the impact on the environment during synthesis 7170-01-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Naidu, B. Narasimhulu; Banville, Jacques; Beaulieu, Francis; Connolly, Timothy P.; Krystal, Mark R.; Matiskella, John D.; Ouellet, Carl; Plamondon, Serge; Remillard, Roger; Sorenson, Margaret E.; Ueda, Yasutsugu; Walker, Michael A.; US2005/267105; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 288-36-8, name is 1H-1,2,3-Triazole, 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. 288-36-8

DMF (1.5 ml) was added to a mixture of methyl S-iodo-beta-methyl-l-pyridinecarboxylate D36 (100 mg), lH-l,2,3-triazole (49.9 mg, 0.722 mmol), (lR,2R)-N,N’-dimethyl-l,2- cyclohexanediamine (10.27 mg, 0.072 mmol), CuI (3.44 mg, 0.018 mmol) and Cs2CO3 carbonate (235 mg, 0.722 mmol) in a microwave vial. The mixture was degassed via three vacuum/nitrogen cycles then irradiated in a single mode microwave reactor to 120 0C for 20 minutes. The mixture was irradiated in a single mode microwave reactor to 120 0C for a further 40 minutes. The reaction mixture was cooled and filtered washing the solids with EtOAc. The solids were dissolved in pH = 3 buffer solution (5 ml); UPLC check of this aqueous solution showed it contained a considerable quantity of 6-methyl-3-(2H- l,2,3-triazol-2-yl)-2-pyridinecarboxylic acid. The aqueous phase was extracted repeatedly with DCM; the combined DCM extracts were diluted with MeOH (50 ml) and treated with TMS-diazomethane. The volatiles were evaporated to give a yellow residue that was purified by flash chromatography on silica gel (Biotage, SNAP 1O g column, 10 %-50 % EtOAc/Cy) to give the title compound D39 (38 mg) as a white solid. UPLC (BasicQC_POS_50-800): rt = 0.57 minutes, peak observed: 219 (M+l). C10H10N4O2 requires 218. 1H NMR (400 MHz, CDCl3) delta ppm 8.20 (d, 1 H), 7.87 (s, 2 H), 7.44 (d, 1 H), 3.94 (s, 3 H), 2.71 (s, 3 H)

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 288-36-8.

Reference:
Patent; GLAXO GROUP LIMITED; ALVARO, Giuseppe; AMANTINI, David; CASTIGLIONI, Emiliano; DI FABIO, Romano; PAVONE, Francesca; WO2010/63662; (2010); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-36-8, The chemical industry reduces the impact on the environment during synthesis 288-36-8, name is 1H-1,2,3-Triazole, I believe this compound will play a more active role in future production and life.

1,2,3-Triazole (3.45 g, 50 mmol),2-iodo-5-methylbenzoic acid (5.24 g, 20 mmol),Cesium carbonate (11.72 g, 36 mmol),Trans-N, N’-dimethyl-1,2-cyclohexanediamine (0.51 g, 3.6 mmol),Cuprous iodide (0.38 g, 2 mmol),N, N-dimethylformamide (30 mL) were sequentially added into a 100 mL single-necked round bottom flask, and the mixture was gradually heated to 100 C. under a nitrogen atmosphere for reaction for 4 hours. The reaction was stopped, cooled, diluted with tap water and extracted with ethyl acetate (200 mL x 2). The aqueous layer was acidified with concentrated hydrochloric acid (pH = 1-2) and extracted with ethyl acetate (200 mL x 2). The combined organic layers were combined and dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated to dryness under reduced pressure and subjected to column chromatography Purification (dichloromethane / methanol (v / v) = 50/1) afforded the title compound (yellow solid, 2.76 g, 68%).

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

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jin Chuanfei; Xu Juan; Zhong Wenhe; Zhang Yingjun; Liu Qi; (35 pag.)CN105949203; (2016); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 16681-65-5, name is 1-Methyl-1H-1,2,3-triazole, 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. 16681-65-5

Compound 6. To a solution of compound 4 (5 g, 60 mmol, 1 eq.) in THF (120 mL) was added LDA (2M in THF, 45 mL, 1.5 eq.) dropwise at -78 C under N2. After the mixture was stirred at -78 C for 1 h, compound 5 (6.33 g, 90.3 mmol, 6.7 mL, 1.5eq.) was added dropwise at -78 C. The mixture was stirred at -78 C for additional 2 h under N2. The reaction mixture was then poured into ice sat. NH4Cl (100 mL) and extracted with DCM (150 mL x 5). The combined organics were washed with brine (200 mL), dried over Na2SO4, filtered, concentrated, and purified by column chromatography (SiO2, petroleum ether/ethyl acetate (1:1 to 0:1)) to afford compound 6 as a yellow solid. 1H-NMR (CDCl3, 400 MHz) delta 7.61 (s, 1H), 4.16-4.12 (m, 1H), 4.11 (s, 3H), 2.82 (d, J = 5.1 Hz, 1H), 1.37 (tq, J = 4.9, 8.2 Hz, 1H), 0.78-0.66 (m, 2H), 0.57-0.48 (m, 1H), 0.42-0.30 (m, 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 16681-65-5.

Reference:
Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM LTD.; SNIR-ALKALAY, Irit; VACCA, Joseph; BEN-NERIAH, Yinon; (238 pag.)WO2019/155468; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

584-13-4, The chemical industry reduces the impact on the environment during synthesis 584-13-4, name is 4H-1,2,4-Triazol-4-amine, I believe this compound will play a more active role in future production and life.

General procedure: In a typical experiment Pd(OAc)2 (5.6mg, 0.025mmol), triphenylphosphine (13.2mg, 0.05mmol), iodoalkene (1-4) or iodoarene (5-19) (1mmol) were dissolved in DMF (10mL) under argon in a three-necked flask equipped with a reflux condenser and a balloon on the top. Aminotriazole nucleophile (a, b or c) (1.2mmol) and triethylamine (0.5mL) were added. The atmosphere was changed to carbon monoxide. (Caution: High pressure carbon monoxide should only be used with adequate ventilation (hood) using CO sensors as well.) The reaction was conducted for the given reaction time upon stirring at 70C. The mixture was then concentrated and evaporated to dryness. Toluene (15mL) was added to the residue, the precipitate (product) was filtered, washed with water on the filter and dried. The off-white powder-like material was dissolved in methanol, the palladium-black was filtered off and methanol was evaporated.

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

Reference:
Article; Gergely, Mate; Boros, Borbala; Kollar, Laszlo; Tetrahedron; vol. 73; 48; (2017); p. 6736 – 6741;,
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 7170-01-6 as follows. 7170-01-6

41. 5-(3-Methyl-1H-1,2,4-triazole-1-yl)-1,6-naphthyridin-2(1H)-one–A stirred mixture containing 13.5 g of 5-bromo-1,6-naphthyridin-2(1H)-one, 20 g of 3-methyl-1H-1,2,4-triazole and 75 ml of N-methylpyrrolidinone was heated in an oil bath at 170-180 C. for 18 hours and then cooled to room temperature whereupon a tan solid crystallized out. The mixture was diluted by adding 125 ml of water and the separated solid was collected, washed with water, air-dried and combined with another 1.2 g sample of the same material obtained in another run starting with 2.25 g of 5-bromo-1,6-naphthyridin-2(1H)-one. The combined solids were recrystallized from dimethylformamide and dried in an oven at 95-100 C. for three days to yield 6.1 g of 5-(3-methyl-1H-1,2,4-triazole-1-yl)-1,6-naphthyridin-2(1H)-one, m.p. >300 C.

According to the analysis of related databases, 7170-01-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sterling Drug Inc.; US4634772; (1987); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

61-82-5, These common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, 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: To a mixture of dimedone (1 mmol), aldehyde (1 mmol), 2-aminobenzimidazole or 3-amino-1,2,4-triazole (1 mmol)and nano-SiO2 (15 mol %) in the acetonitrile (5 mL) was stirred for appropriate time (Table 2) at 25-30 C. After the completion of the reaction as indicated by TLC, dichloromethane (CH2Cl2) was added to the solidified mixture and the insoluble catalyst was separated by filtration. Evaporation of the solvent from the filtrate and recrystallization of the solid residue from hot ethanol afforded the pure products in high yields.

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 61-82-5.

Reference:
Article; Mousavi, Mir Rasul; Maghsoodlou, Malek Taher; Journal of the Iranian Chemical Society; vol. 12; 5; (2015); p. 743 – 749;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

7170-01-6, These common heterocyclic compound, 7170-01-6, name is 3-Methyl-1H-1,2,4-triazole, 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.

To a solution of 50 (1.08 g, 4.03 mmol) in DMF (20 mL) was added3-methyl-1H-1,2,4-triazole (0.469 g, 5.65 mmol) and K2CO3(0.781 g, 5.65 mmol) at r.t. The mixture was stirred at r.t.overnight and warmed to 60C for 2 h. After cooling to r.t.,water was added to the mixture. The solid was collected byfiltration, washed with water, and dried to give 51b (0.870 g,2.77 mmol, 69%) as a tan solid. 1H-NMR (300 MHz, DMSOd6) delta: 1.56 (9H, s), 2.43 (3H, s), 2.54 (3H, d, J=1.1 Hz), 8.56(1H, s), 9.10 (1H, s), 9.43 (1H, d, J=1.1 Hz). MS (ESI/APCI)m/z 315.2 [M+H]+.

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:
Article; Mikami, Satoshi; Kawasaki, Masanori; Ikeda, Shuhei; Negoro, Nobuyuki; Nakamura, Shinji; Nomura, Izumi; Ashizawa, Tomoko; Kokubo, Hironori; Hoffman, Isaac Dylan; Zou, Hua; Oki, Hideyuki; Uchiyama, Noriko; Hiura, Yuuto; Miyamoto, Maki; Itou, Yuuki; Nakashima, Masato; Iwashita, Hiroki; Taniguchi, Takahiko; Chemical and Pharmaceutical Bulletin; vol. 65; 11; (2017); p. 1058 – 1077;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics