Tag: M.W=0-100

Adding a certain compound to certain chemical reactions, such as: 7170-01-6, name is 3-Methyl-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 7170-01-6, Quality Control of 3-Methyl-1H-1,2,4-triazole

A suspension of 6-bromo-7-(dimethoxymethyl)-I ,2,3,4-tetrahydro-I ,8-naphthyridine (intermediate12) (300 mg, 1.045 mmol), 3-methyl-I H-I ,2,4-triazole (104 mg, 1.254 mmol), Cs2CO3 (720 mg,2.210 mmol) and Cul (40 mg, 0.210 mmol) in DMF (2 ml) was heated to 120 C for approximately 6 h. The reaction mixture was diluted with ethyl acetate and water, layers were separated and the aqueous layer was extracted with ethyl acetate (3x). Organic layers were combined, washed with water and brine, dried using Na2SO4, filtered, evaporated. The crude product was purified by silica gel column chromatography eluting with a gradient of MeOH (1-10%) in DCM. Product fractionswere combined, evaporated and dried to yield the title compound as an orange resin. (UPLC-MS 3)tR 0.57 mm; ESI-MS 290.1 [M+H]+. 1H NMR (400 MHz, CDCI3) 5 8.21 (s, I H), 7.21 (s, I H), 5.35 (s, I H), 4.95 (s, I H), 3.51 – 3.41 (m, 2H), 3.36 (s, 6H), 2.75 (t, 2H), 2.47 (s, 3H), 1.97 – 1.86 (m, 2H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Methyl-1H-1,2,4-triazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NOVARTIS AG; BUSCHMANN, Nicole; FAIRHURST, Robin Alec; FURET, Pascal; KNOePFEL, Thomas; LEBLANC, Catherine; MAH, Robert; NIMSGERN, Pierre; RIPOCHE, Sebastien; LIAO, Lv; XIONG, Jing; ZHAO, Xianglin; HAN, Bo; WANG, Can; WO2015/59668; (2015); 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. 288-36-8, name is 1H-1,2,3-Triazole, A new synthetic method of this compound is introduced below., name: 1H-1,2,3-Triazole

But-3-yn-1-ol (49.57 g, 707.2 mmol) and triethylamine (107.7 mL, 777 mmol, dried over KOH) were dissolved in dry dichloromethane (500 mL) under a nitrogen atmosphere and cooled to 0 C. Methanesulfonyl chloride (54.8 mL, 708 mmol), dissolved in 500 mL of dry dichloromethane was added within 90 minutes while keeping the temperature below 5 C. The mixture was stirred for 3.5 hours at room temperature, then poured onto 2.5 L of ice water. The organic phase was separated and washed with 2¡Á500 mL of water and 1¡Á250 mL of brine and dried over sodium sulfate. The volatiles were removed to yield 94.18 g of the methane sulfonate (631.2 mmol, 89.2%) as a yellow liquid. A suspension of NaOH (37.86 g, 946.5 mmol), sodium iodide (94.65 g, 631.5 mmol) and 1H-[1,2,3]Triazole (61.03 g, 883.6 mmol) in 2-methyl-2-butanol (750 mL) was refluxed for 1 h under an inert atmosphere. After cooling to room temperature the methane sulfonate (94.18 g, 631.2 mmol) was added within 5 minutes. The resulting suspension was then heated to reflux for 3 hours, cooled to room temperature and concentrated on a rotary evaporator at 45 C. Water (500 mL) and dichloromethane (1 L) were added and the organic phase was separated, dried over sodium sulfate and the volatiles removed at 30 C. The residue was distilled at 1 mmHg . A forerun was collected at 20-70 C. The main fraction distilled at 123-129 C. as a colorless, turbid liquid. After filtration over Celite (filtration over a pad of diatomite) 1-But-3-ynyl-1H-[1,2,3]triazole was obtained as a colorless liquid (29.8 g, 40%). The content according to GC/FID was >98%. 1H-NMR (CDCl3) delta=2.05 (t, 1H, C?CH), 2.75 (dt, 2H, CH2-C?CH), 4.5 (t, 2H, CH2-triazole), 7.65 (s, 1H, triazole), 7.70 (s, 1H, triazole).

The synthetic route of 288-36-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bossenmaier, Birgit; Friebe, Walter-Gunar; Georges, Guy; Rueth, Matthias; Voss, Edgar; US2005/197370; (2005); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 584-13-4, name is 4H-1,2,4-Triazol-4-amine, molecular formula is C2H4N4, 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. COA of Formula: C2H4N4

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.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 584-13-4, its application will become more common.

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

Synthetic Route of 60166-43-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 60166-43-0 name is 1,4-Dimethyl-1H-1,2,3-triazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

In a pressure vessel equipped with a magnetic stirring bar, was added (Patent; BRISTOL-MYERS SQUIBB COMPANY; NORRIS, Derek J.; VACCARO, Wayne; DEBENEDETTO, Mikkel V.; DEGNAN, Andrew P.; DELUCCA, George V.; DESKUS, Jeffrey A.; HAN, Wen-Ching; KUMI, Godwin Kwame; SCHMITZ, William D.; STARRETT, John E., JR.; HILL, Matthew D.; HUANG, Hong; (563 pag.)WO2016/183118; (2016); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 27808-16-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 27808-16-8 name is 4-Methyl-1H-1,2,3-triazole, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of 4-methyl-iH-i,2,3-triazole (500 mg,6.02 mmol), 2,3-dichloro-5-nitropyridine (1277.42 mg, 6.62 mmol), K2C03 (2491.22 mg, 18.05 mmol) in CH3CN (5 mE) was stirred at it for 12 h. The mixture was concentrated under reduced pressure, the crude product was purified by colunm chromatography over silica gel (petroleum ether ethyl acetate from 20:1 to 1:1). The desired fractions were collected and the solvent was concentrated under reduced pressure to afford i25a (1.1 g, 76.3%) as a yellow solid. ECMS (ESI) mlz M+i: 239.7. Zn (1491.96 mg, 22.95 mmol) was added to a solution of mixture of 3-chloro-2-(4-methyl-2H-i,2,3-tri- azol-2-yl)-5-nitropyridine and 3-chloro-2-(4-methyl-i H-i, 2,3-triazol-i-yl)-5-nitropyridine, i25a (1.1 g, 2.30 mmol) in aqNH4C1 (30 mE) and H20 (30 mE). The mixture was stirred at it for 16 h. To the suspension was added aq NaHCO3 to adjust to pH 9-10, and the mixture was filtered through a pad of diatomaceous earth. The filter cake was washed with CH2C12 (100 mEx3). The combined filtrates were washed with brine (200 mE), dried over MgSO4 and concentrated under reduced pressure to afford mixture of 5-chloro-6-(4-methyl-2H- 1 ,2,3-triazol-2-yl)pyridin-3-amine and 5-chloro-6-(4-methyl-i H-i ,2,3-triazol- 1 -yl)pyriF din-3-amine, 125b (1 g) as a brown solid, used directly for the next step. LCMS (ESI) mlz M+H: 209.7

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methyl-1H-1,2,3-triazole, and friends who are interested can also refer to it.

Reference:
Patent; Janssen Biotech, Inc.; Lu, Tianbao; Allison, Brett Douglas; Barbay, Joseph Kent; Connolly, Peter J.; Cummings, Maxwell David; Diels, Gaston; Edwards, James Patrick; Kreutter, Kevin D.; Philippar, Ulrike; Shen, Fang; Thuring, Johannes Wilhelmus John Fitzgerald; Wu, Tongfei; (412 pag.)US2018/170909; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 74205-82-6, These common heterocyclic compound, 74205-82-6, name is (1H-1,2,4-Triazol-1-yl)methanol, 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.

Example4. Synthesis of Intermediate 5Intermediate 4 (16.3g, 70.4 mmol) was completely dissolved in concentrated sulfuric acid (80ml) under ice bath, and triazolemethanol (10.4g) was added. The solution was stirred at room temperature for 5hrs. TLC was used toshow the completion of raw materials. Post-treatment: the reaction solution wasslowly added to 20% sodium hydroxide solution under ice bath. After alkalizing,dichloromethane was added to extract the product. The organic layer was driedand the solvent was removed by rotary evaporation. 21.2g yellow oil product(crude) was obtained. 15.6g light yellowsemi-solid (Intermediate 5) was obtained after column chromatography separation(dichloromethane: methanol 20: 1+ 1% triethylamine) and rotary evaporation,with a yield of 71.0%.

The synthetic route of 74205-82-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Wu, Yong; Hai, Li; Sun, Baohou; He, Yi; Li, Xiaocen; (11 pag.)CN103664900; (2016); B;,
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. 10570-40-8, name is 4-Methyl-4H-1,2,4-triazole, A new synthetic method of this compound is introduced below., category: Triazoles

4.2 1-(4-Methyl-4H-1,2,4-triazol-3-yl)octan-1-ol To a solution of 4-methyl-1,2,4-triazole (681 mg, 7.78 mmol), TMEDA (0.40 ml) in dry THF (10 ml) and at -60 C, 2.69 M n-BuLi solution (2.9 ml, 7.80 mmol) was added drop wise. After stirring at -60 C for 30 min, 10 ml of dry THF solution of octanol (1.30 mL, 8.33 mmol) was added and the mixture was stirred for additional 4 h at -60 C to -30 C. Then H2O was added and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1-5% methanol/chloroform) as a colorless solid (1.13 g, 69%): Mp. 63-65 C; 1H NMR (500 MHz, CDCl3) delta 0.87 (3H, t, J = 6.6 Hz), 1.30-1.26 (9H, m), 1.46 (1H, q, J = 5.2 Hz), 1.93-1.84 (2H, m), 3.50 (1H, br s), 3.93 (3H, s), 4.82 (1H, q, J = 6.3 Hz), 7.76 (1H, s); 1H NMR (300 MHz, DMSO) delta 0.88 (3H, t, J = 6.9 Hz), 1.26-1.49 (14H, m), 1.87-1.93 (2H, m), 2.70 (1H, d, J = 7.5 Hz) 3.92 (3H, s), 4.84 (1H, q, J = 6.9 Hz), 7.79 (1H, s); 13C NMR (126 MHz) delta 14.1, 22.7, 25.2, 29.5, 31.9, 33.7, 35.4, 39.8, 64,2, 143.6, 155.0; HRMS (ESI) m/z calcd for C11H21N3NaO (M + Na)+ 234.1582, found. 234.1573.

The synthetic route of 10570-40-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Suzuki, Yumiko; Iwata, Naoto; Dobashi, Kohei; Takashima, Ryo; Arulmozhiraja, Sundaram; Ishitsubo, Erika; Matsuo, Naoya; Tokiwa, Hiroaki; Tetrahedron; vol. 74; 3; (2018); p. 392 – 400;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 61-82-5,Some common heterocyclic compound, 61-82-5, name is 1H-1,2,4-Triazol-5-amine, molecular formula is C2H4N4, 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: A mixture of 3-amino-1,2,4-triazole or benzimidazole (1.0 mmol), benzaldehyde (1.0 mmol), dimedone (1.0 mmol), and acetonitrile (5 mL) was taken in a round bottom flask and added iodine (10 mol %) and stirred at 80 C for 10 min. After completion of the reaction, as monitored by TLC, the reaction mass was cooled to room temperature and the solid separated was filtered and washed with water and dried at reduced pressure.Data of representative examples

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1H-1,2,4-Triazol-5-amine, its application will become more common.

Reference:
Article; Puligoundla, Ravinder Goud; Karnakanti, Shuklachary; Bantu, Rajashaker; Nagaiah, Kommu; Kondra, Sudhakar Babu; Nagarapu, Lingaiah; Tetrahedron Letters; vol. 54; 20; (2013); p. 2480 – 2483;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 584-13-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 584-13-4 name is 4H-1,2,4-Triazol-4-amine, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To the solution of 4-amino-4H-1,2,4-triazole (0.0059 mol, 0.500 g) in an hydrous acetonitrile (20 mL), an N-alkyl or N-arylisothiocyanate (0.0065 mol) was introduced, and the obtained mixture was stirred at room temperature for 16h. Then the solvent was evaporated. The main compound was isolated from the reaction mixture by column chromatography (CHCl3: CH3OH; 9.5:1 vol.) or crystallized from acetonitrile.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4H-1,2,4-Triazol-4-amine, and friends who are interested can also refer to it.

Reference:
Article; Bielenica, Anna; Kedzierska, Ewa; Fidecka, Sylwia; Maluszynska, Hanna; Miroslaw, Barbara; Koziol, Anna E.; Stefanska, Joanna; Madeddu, Silvia; Giliberti, Gabriele; Sanna, Giuseppina; Struga, Marta; Letters in drug design and discovery; vol. 12; 4; (2015); p. 263 – 276;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 41253-21-8, 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 41253-21-8 as follows.

To a solution of 4-cyclohexyl-4-methansulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester (39 g, 103.8 mmol) in N,N-dimethylformamide (200 mL) is added sodium triazole (38 g, 415.2 mmol). The resulting solution is heated to 100 C. for 24 hours then cooled to room temperature. The solvent is removed under reduce pressure and the crude product purified over silica (80:20 EtOAc:hexane) to afford 28.7 g (79.7% yield) of the desired compound as a colorless solid. 1H NMR (CD3OD) delta 0.95-1.90 (m, 15H), 1.46 (s, 9H), 3.45-3.55 (m, 4H), 4.34 (s, 2H), 7.99 (s, 1H), 8.48 (s, 1H). MS (ESI) m/z 349, (M+H+), 371(M+Na+)

According to the analysis of related databases, 41253-21-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; The Procter & Gamble Company; US2003/236230; (2003); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics