Triazoles

Application of 3641-13-2,Some common heterocyclic compound, 3641-13-2, name is 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, molecular formula is C3H4N4O2, 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 benzil (0.01 mol), aldehydes (0.01 mol), 3-amino-1,2,4-triazole-5-carboxylic acid (0.01 mol), ammonium acetate (0.01 mol) and ceric ammonium nitrate (15 mol%) as a catalyst were refluxed in ethanol (15 mL) for about 3-4 h. The progress of the reaction was monitored by TLC. After completion of reaction, the mixture was cooled to room temperature. The solid formed was filtered and dried. The crude products were recrystallized by ethanol.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-4H-1,2,4-triazole-3-carboxylic acid, its application will become more common.

Reference:
Article; Nikalje, Anna Pratima G.; Ghodke, Mangesh S.; Kalam Khan, Firoz A.; Sangshetti, Jaiprakash N.; Chinese Chemical Letters; vol. 26; 1; (2015); p. 108 – 112;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

These common heterocyclic compound, 1533519-84-4, name is 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione, 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. Safety of 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione

Compound 10 was synthesized with reference to Patent CN10352440A reported. Compound 10 (50. 00mg,187 ¡¤ 02umol, 1 ¡¤ OOeq), compound 14 (54. 56mg, 224. 42umol, 1 ¡¤ 20eq) and potassium carbonate (31. 02mg,224. 42umol, 1.20eq) were dissolved in N, Nu- dimethylformamide (10. OOmL), and the reaction was stirred between 15 C under 2.5 hours. After completion of the reaction, the reaction solution was spin-dried to give the crude product as a yellow solid. The crude product is purified by PTLC thin layer chromatography (developingSolvent: 50% ethyl acetate / petroleum ether) to give compound 15 as a colorless oil.

The synthetic route of 4-(4-Cyclopropylnaphthalen-1-yl)-1H-1,2,4-triazole-5(4H)-thione has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Matilda drug R & D Co., Ltd.; Wang, Jainfei; Zhang, Jing; Zhang, Long; Zhang, Yang; Li, Jian; Chen, Shuhui; (43 pag.)CN105622531; (2016); A;,
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. 103755-58-4, name is (1-Phenyl-1H-1,2,3-triazol-4-yl)methanol, A new synthetic method of this compound is introduced below., category: Triazoles

General procedure: Into a round bottom flask was added 5.71mmolof triazole type 12 or 21a in 50mL of dry THF, 17.13mmolof sodium hydride and 57.1mmolof alkyl bromide. The mixture was heated to reflux, and reaction progress was monitored by TLC. Subsequently, the solvent was evaporated and the mixture was extracted with ethyl acetate, washed with distilled water (3¡Á100mL) and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the product was purified via silica-gel column chromatography using a gradient mixture of hexane-ethyl acetate, to afford the pure derivatives 14a-g and 23a-b.

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:
Article; Gonzaga, Daniel; Senger, Mario Roberto; Da Silva, Fernando De Carvalho; Ferreira, Vitor Francisco; Silva Jr., Floriano Paes; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 461 – 476;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Electric Literature of 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 4-fluorobenzaldehyde (3.63 g) and 3-methyl-lH-l,2,4-triazole (2.92 g; prepared according to US 2006/293304) in dry DMF (35 mL) was added K2C03 (24.25 g) at rt. The reaction mixture was stirred at 120C overnight, then cooled to rt and diluted with EA and water. The aq. layer was extracted with EA (2x) and the combined org. layers were washed with water and brine, dried over MgS04, filtered and concentrated under reduced pressure. The title compound was obtained, after purification by CC (Hept/EA 80:20 to 50:50), as a yellow solid (36% yield).1H NMR (CDCls) delta: 10.06 (s, 1H); 8.58 (s, 1H); 8.04 (d, J = 8.0 Hz, 2H); 7.88 (d, J = 8.0 Hz, 2H); 2.53 (s, 3H).

The synthetic route of 7170-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BUR, Daniel; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe; WO2011/121555; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 28938-17-2,Some common heterocyclic compound, 28938-17-2, name is 4,5-Dibromo-2-methyl-2H-1,2,3-triazole, molecular formula is C3H3Br2N3, 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.

Example 1 3.0 g (12.45 mmol) of 2-methyl-4,5-dibromo-2H-1,2,3-triazole was dissolved in 25 ml of tetrahydrofuran, cooled to -20?-10C, 6.85 ml (13.7 mmol) of 2.0M isopropylmagnesium chloride tetrahydrofuran solution was added dropwise slowly in 30 minutes. Added dropwise was completed, continued to stir for 30?60 minutes. Chlorine was inleted slowly until reaction liquid was no longer heating up. Reaction liquid was added by 20 ml of saturated ammonium chloride aqueous solution, extracted by using 30 ml of methyl tertiary butyl ether, dried by anhydrous sodium sulfate, concentrated to dry under reduced pressure, the residual solid was added by 20 ml of methyl tertiary butyl ether/n-hexane (1/5), heated to reflux for 1 hour, cooled to 0?10C, continued to be stirred for 1 hour, filtered, vacuum dried under a temperature <40C. 2.06 g of 2-methyl-4-bromo-5-chloro-2H-1,2,3-triazole solid was obtained, the yield was 85%. 1H NMR (CDCl3, 400 MHz): delta 4.15 (s, 3H); 13C NMR (CDCl3, 400 MHz): delta 137.0, 120.8, 43.1. The synthetic route of 28938-17-2 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ABA Chemicals Corporation; JIANG, Yueheng; QUE, Limin; CAI, Tong; QIN, Dongguang; EP2889292; (2015); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Reference of 27996-86-7, 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 27996-86-7 as follows.

General procedure: To a glass vessel suitable for sealing with Teflon cap (for microwave vials) were added 1-(chloromethyl)-4,5-dimethoxy-2-nitrobenzene (1 equiv.) [34] and benzaldehyde derivative (3 equiv.) The vessel was capped and then evacuated and backfilled with N2 (thrice-repeated process). Anhydrous DMF (3.5mL/mmol) was introduced and the solution was vigorously stirred for 20minat-20C. TDAE (1.06 equiv.) was added slowly and the mixture was stirred for one hour. Then, the reaction was stirred at room temperature overnight. After LC-MS analysis clearly showed that the chloride had been totally consumed, the reaction was hydrolyzed with water. The mixture was then extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered off, and concentrated under reduced pressure to afford the corresponding crude product.

According to the analysis of related databases, 27996-86-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Da Costa, Laurene; Scheers, Els; Coluccia, Antonio; Rosetti, Alessia; Roche, Manon; Neyts, Johan; Terme, Thierry; Cirilli, Roberto; Mirabelli, Carmen; Silvestri, Romano; Vanelle, Patrice; European Journal of Medicinal Chemistry; vol. 140; (2017); p. 528 – 541;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 6818-99-1, name is 3-Chloro-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Chloro-1,2,4-triazole

STR18 A mixture of 34 g (246 mmol) of potassium carbonate and 35 g (338 mmol) of 3-chloro-1,2,4-triazole in 130 ml of acetone is refluxed. To this mixture there is added dropwise a solution of 50 g (169 mmol) of 2-bromo-4-chloro-1-(4-chlorophenyl)-butan-1-one in 60 ml of acetone. The mixture is boiled under reflux for a further 8 hours, the solid residue is then filtered off with suction, and the solvent is stripped off under reduced pressure. The residue which remains is taken up in ethyl acetate. The solution is washed with water, dried over sodium sulphate and concentrated under reduced pressure. The residue which remains is chromatographed on silica gel using dichloromethane as the eluent. Concentration of the elude by evaporation gives 42.9 g (90% of theory) of 1-(4-chlorobenzoyl)-1-(3-chloro-1,2,4-triazol-1-yl)-cyclopropane in the form of a solid of melting point 85 C.

According to the analysis of related databases, 6818-99-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Aktiengesellschaft; US5096913; (1992); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 16681-70-2, 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. 16681-70-2, name is 1H-[1,2,3]Triazole-4-carboxylic acid belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

A solution of 1H-1,2,3-triazole-4-carboxylic acid (26 mg, 0.23 mmol) and HBTU (171 mg, 0.45 mmol) in a mixed solvent of dimethyl sulfoxide (2 mL) and tetrahydrofuran (4 mL) was stirred for 10 min at rt, then (+/-) -cis-6- ( (3-aminocyclohexyl) amino) -2- (5, 7-difluoro -1-tosyl-1H-indol-3-yl) -5-fluoro-4-phenylnicotinonitrile (92 mg, 0.15 mmol) and DIPEA (0.10 mL, 0.61 mmol) were added into the mixture. The resulting mixture was stirred at rt overnight. To the reaction mixture was added water (30 mL) , and the mixture was extracted with EtOAc (30 mL ¡Á 3) . The combined organic layers were washed with a saturated aqueous sodium chloride solution (60 mL) , dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo to dry, and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) 5/1 1/5) to give the title compound as a white solid (78 mg, 73 %) . 1H NMR (400 MHz, CDCl3) delta (ppm) : 8.66 (s, 1H) , 8.20 (s, 1H) , 7.93 (d, J 8.0 Hz, 2H) , 7.71 (d, J 8.9 Hz, 1H) , 7.55 (s, 5H) , 7.31 (d, J 8.3 Hz, 2H) , 7.00 (s, 1H) , 6.84 (t, J 9.3 Hz, 1H) , 5.22 (d, J 5.7 Hz, 1H) , 4.30 (s, 1H) , 4.14 (d, J 7.2 Hz, 1H) , 2.58 (d, J 11.1 Hz, 1H) , 2.39 (s, 3H) , 2.29 (d, J 11.3 Hz, 1H) , 2.17 (d, J 11.0 Hz, 1H) , 1.97 (d, J 14.3 Hz, 1H) , 1.63 (m, 4H) .

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, 1H-[1,2,3]Triazole-4-carboxylic acid, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; TANG, Changhua; REN, Qingyun; YIN, Junjun; YI, Kai; ZHANG, Yingjun; (161 pag.)WO2018/41091; (2018); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Synthetic Route of 288-88-0, 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. 288-88-0, name is 1H-1,2,4-Triazole belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below.

Example 91: Preparation of 4-(lH-l,2,4-triazol-l-yl)benzaldehyde (DI5) To a stirring solution of 4-fluorobenzaldehyde (10.0 g, 80.6 mmol) in DMF (150 mL) were added K2CO3 (13.3 g, 96.7 mmol) and 1,2,4- triazole (6.67 g, 96.7 mmol) and the resultant reaction mixture was stirred at 120 C for 6 h. After completion of reaction (by TLC), the reaction mixture was diluted with H20 and extracted with EtOAc (3 xlOO mL). The combined EtOAc layer was washed with H20 and brine, dried over Na2S04, and concentrated under reduced pressure to afford the title compound as a solid (9.0 g, 65%): mp 145-149 C: ]H NMR (400 MHz, CDC13) delta 10.08 (s, IH), 8.70 (s, IH), 8.16 (s, IH), 8.06 (d, J = 8.0 Hz, 2H), 7.92 (d, J = 8.0 Hz, 2H); ESIMS m/z 173.9 ([M+H]+).

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

Reference:
Patent; DOW AGROSCIENCES LLC; LO, William C.; HUNTER, James E.; WATSON, Gerald B.; PATNY, Akshay; IYER, Pravin S.; BORUWA, Joshodeep; WO2014/100163; (2014); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 23579-79-5, name is 3,5-Dibromo-1-methyl-1H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C3H3Br2N3

A mixture of 1,2,3, 4-tetrahydroisoquino line (1.1 g, 8.3 mmol), intermediate 32 (0.2 g, 8.3 mmol), K2C03 (2.3 g, 16.6 mmol) in DMF (20 ml) was heated at 160 C for 45 min using microwave irradiation. The r.m. was cooled and then poured onto 1?0 and extracted with DCM. The organic layer was dried (MgSC^) and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel (eluent: DCM/MeOH from 100/0 to 97/3). The product fractions were collected and concentrated in vacuo, yielding 900 mg of intermediate 33 (40 %).

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 23579-79-5.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC; VAN BRANDT, Sven, Franciscus, Anna; DE CLEYN, Michel, Anna, Jozef; GIJSEN, Henricus, Jacobus, Maria; BERTHELOT, Didier, Jean-Claude; SURKYN, Michel; WO2011/86099; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics