Category: Triazoles

Electric Literature of 1157938-97-0, 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 1157938-97-0 as follows.

The thus obtained LDA-solution (3.66 mL, 0.98 mmol, 1.1 eq) was transferred to a Schlenk vessel and ethylpropionate (100 mg, 0.98 mmol, 1.1 eq.) was added in a drop wise fashion at -78 C. under a nitrogen atmosphere. The resulting mixture was stirred at -78 C. for 30 minutes and then 1-(2,5-difluorophenyl)-2-(lII-1,2,4-triazol-1-yl)ethanone (200 mg, 0.90 mmol, 1.0 eq.) in THF (3.66 mL) was added in a drop wise fashion over 15 minutes. The reaction mixture was stirred for 2 hours at -78 C. and then quenched with acetic acid and warmed to room temperature. The mixture was diluted with aqueous saturated NH4Cl and ethylacetate. The aqueous layer was extracted with ethylacetate (2¡Á) and the combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give a yellow oil containing the racemic ester I with a diastereomeric excess of 29% in favour of the desired RR/SS diastereomer. Further purification by column chromatography (n-heptane/EtOAc/MeOH 60/40/5 v/v/v) provided the RR/SS diastereomer (light yellow solid) as well as the RS/SR diastereomer (off-white solid) in a combined overall yield of 179 mg (0.55 mmol, 61%).

According to the analysis of related databases, 1157938-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Basilea Pharmaceutica AG; Van Summeren, Ruben; Vaessen, Harrie; Mink, Daniel; Waser, Mario; (11 pag.)US2019/77771; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

288-88-0, name is 1H-1,2,4-Triazole, belongs to Triazoles compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 1H-1,2,4-Triazole

, adding 50 mmol of sodium methoxide into 50 mmol of 1, 2, 4-triazole (shown in the formula II)) and 50 mL of methanol solution, stirring for 60 minutes at 40 DEG c, and dropwise adding 60 mmol of bromobenzene, carrying out condensation reflux for 16 hours at the temperature of 90 DEG c, removing volatile matters in the reaction raffinate, washing the carbon tetrachloride, and filtering the solid impurities, and carrying out rotary evaporation to remove the washing solvent to obtain colorless liquid 1-phenyl -1,2,4-triazole 6.32g

The synthetic route of 288-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Tech University; Guan Guofeng; He Yuting; Ding Jing; Li Xue; Wan Hui; (9 pag.)CN108484654; (2018); A;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 7343-33-1, These common heterocyclic compound, 7343-33-1, name is 5-Bromo-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.

Example 59. Preparation of 3-bromo-l-(4-(trifluoromethoxy)phenyl)-lH-l,2,4-triazole (B61) To a 250 mL reaction flask was added 3-bromo-lH-l,2,4-triazole (5 g, 33.8 mmol), copper(I) iodide (0.644 g, 3.38 mmol) and cesium carbonate (11.01 g, 33.8 mmol). The flask was evacuated/backfilled with N2, then DMSO (33.8 ml) and l-iodo-4-(trifluoromethoxy)benzene (4.87 g, 16.90 mmol) were added. The reaction mixture was heated to 100 ¡ãC for 20 h. The reaction was cooled to room temperature, diluted with EtOAc and filtered through a plug of Celite. The Celite was further washed with EtOAc. Water was added to the combined organics, and the layers were separated. The aqueous phase was neutralized to pH 7, and further extracted with EtOAc. The combined organics were concentrated in vacuo. Purification via flash chromatography (silica/EtO Ac/Hex) yielded 3-bromo-l-(4- (trifluoromethoxy)phenyl)-lH-l,2,4-triazole as an off white solid (3.78 g, 12.27 mmol, 72.6percent): mp 69-70 ¡ãC; ]H NMR (400 MHz, CDC13) delta 8.44 (s, 1H), 7.70 (d, / = 8.9 Hz, 2H), 7.38 (d, J = 8.5 Hz, 2H); 19F NMR (376 MHz, CDC13) delta -58.04; EIMS m/z 307.

The synthetic route of 7343-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; CROUSE, Gary D.; DEMETER, David A.; SPARKS, Thomas C.; WANG, Nick X.; DENT, William Hunter; DEAMICIS, Carl; NIYAZ, Noormohamed M.; BAUM, Erich W.; FISCHER, Lindsey G.; GIAMPIETRO, Natalie C.; FRITZ, Amanda E.; WO2014/11429; (2014); 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. HPLC of Formula: C2HBr2N3

In a 100 mL round-bottomed flask. 3.5-dibromo- 1 H- 1.2.4-triazole (5g, 22.0 mmol. Eq: 1.00), 1 – (chloromethyl)-4-methoxybenzene (3.45 g. 22.0 mmol. Eq: 1) and N-ethyl-N-isopropylpropan-2- amine (5.7 g. 44. 1 mmol. Eq: 2) were combined with acetonitrile (101 ml ) to give a light yellow solution. Potassium iodide (1.83 g, 11.0 mmol, Eq: 0.5) was added. The mixture was heated to reflux for 2 hours. The reaction mixture was cooled and diluted with EtOAc (100 mL), washed with H20 (50 mL) and brine (50 mL). The organic layer was dried over anhydrous MgS04, filtered and volatiles were removed under reduced pressure to yield an oil from which the compound was isolated by column chromatography (Hexanes/EtOAc = 70/30) to give 7.3 g of desired product (95%).

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:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHEN, Zhi; CHIN, Elbert; ERICKSON, Shawn David; GABRIEL, Stephen Deems; MERTZ, Eric; WEIKERT, Robert James; WO2014/135483; (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. 16227-12-6, name is 4-Phenyl-4H-1,2,4-triazole, This compound has unique chemical properties. The synthetic route is as follows., category: Triazoles

EXAMPLE 127 4-phenyl-1-(pent-1-yl)triazolium bromide 0.15 g (0.001 mol) 4-phenyltriazole 1 and 0.37 ml (0.45 g, 0.003 mol) 1-bromopentane 2 are combined in a pressure tube. The mixture is stirred 12 h at 110 C. Subsequently, it is cooled down to room temperature. The precipitated solid is taken up in a 1:1 mixture of THF and petroleum ether, is filtered off, and washed with diethylether. M 296.21 C13H18N3Br Yield: 0.231 g (78%) 1H-NMR DM-229 (300 MHz/DMSO): (ppm)=0.88 (t, 3H, 11-H); 1.37 (m, 4H, 9); 1.96 (q, 2H, 8-H); 4.44 (t, 2H, 7-H); 7.69 (m, 3H, 5/5’/6H); 7.85 (d, 2H, 4/4′-H); 9.81 (s, 1H, 2-H); 10.86 (s, 1H, 1-H) 13C-NMR DM-229 (75.475 MHz/DMSO):

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 16227-12-6.

Reference:
Patent; TECHNISCHE UNIVERSITAET DRESDEN; US2011/105761; (2011); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

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. 15988-11-1, name is 4-Phenyl-1,2,4-triazolidine-3,5-dione belongs to Triazoles compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 4-Phenyl-1,2,4-triazolidine-3,5-dione

General procedure: A mixture of dimedone (1, 1 mmol), 4-phenylurazole (2, 1 mmol), aromatic aldehyde (3a-h, 1mmol) and S-LCCO nano perovskite (0.01 g) was mixed in a high-pressure Teflon reactor, which was equipped with a magnetic stirrer and an optical fiber, which was implemented to control the reaction’s temperature. The reaction mixture was irradiated by 400 W microwave at 80 oC, for the specified reaction times. TLC with n-hexan:ethylacetate eluent was used to monitor the progress of the reactions. After reaction completion and cooling, the reaction mixtures were filtered and washed with ethanol to separate the catalyst. First, 10 mL water was added to the solution. Then, EtOH/H2O (4:1) was added to crystallize the water insoluble crude products. Then the crystals were filtered to achieve pure products (4a-h).

The synthetic route of 15988-11-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zahedi, Najmeh; Javid, Ali; Mohammadi, Mohammad Kazem; Tavakkoli, Haman; Bulletin of the Chemical Society of Ethiopia; vol. 32; 2; (2018); p. 239 – 248;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Related Products of 23579-79-5, A common heterocyclic compound, 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, such as complicated route, low yield, poor purity, etc, 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 synthetic route of 23579-79-5 has been constantly updated, and we look forward to future research findings.

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

Synthetic Route of 288-88-0, 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. 288-88-0, name is 1H-1,2,4-Triazole, This compound has unique chemical properties. The synthetic route is as follows.

Weigh p-iodoaniline (300.0mg, 1.37mmol), 1H-1,2,4- Triazole (113.4mg, 1.64mmol), CuI (26.0mg, 0.14mmol), cesium carbonate (624.7mg, 1.92mmol), 8-hydroxyquinoline (39.7mg, 0.27mmol) was placed in a 50mL single-necked flask, and mixed The solvent DMF: H2O (10: 1) was reacted at 110 C for 24 hours. After confirming the completion of the reaction by TLC, water was added, EA was extracted, and anhydrous sodium sulfate was dried. After concentration, it was purified through a silica gel column using a mobile phase with petroleum ether and ethyl acetate (V / V = 1/1) to obtain 4- (1H- 1,2,4-triazol-1-yl) aniline 3r was used as the starting material for the next reaction.

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

Reference:
Patent; Wuhan University; Wu Shuwen; Zhou Haibing; Xu Zhichao; (24 pag.)CN110483425; (2019); A;,
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.

A solution of 2,4-difluorobenzonitrile (7.07 g, 50.8 mmol) and 3-methyl-lH- 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 18h. 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.Intermediate 814Fluoro-2-(3-methyl-lH-l,2,4-triazol-l-yl)benzonitrile. White crystals (ethyl acetate-hexane); mp 117-118 0C. 1HNMR 400 MHz (CDCl3) delta ppm: 2.54 (3H, s, CH3), 7.24 (IH5 m, CH), 7.62 (IH, dd, J = 2.5 Hz and J = 9.1 Hz, CH), 7.84 (IH, dd, J = 5.6 Hz and J = 8.6 Hz, CH), 8.82 (IH, 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. Intermediate 824-Fluoro-2-(5-methyI-lH-l,2,4-fiiazoI-l-yl)benzonifrile. White crystals(ethyl acetate-hexane); mp 120-121 C. 1HNMR 400 MHz (CDCl3) delta ppm: 2.56 (3H, s, CH3), 7.30 (IH, dd, J = 2.5 Hz and J = 8.1 Hz, CH), 7.39 (IH, m, CH), 7.91 (IH, dd, J = 5.5 Hz and J = 8.6 Hz, CH), 8.06 (IH, 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.Intermediate 832-Fluoro-4-(3-methyl-lH-l,2,4-triazol~l-yl)benzonitrile. White crystals(ethyl acetate-hexane); mp 133-134 C. 1HNMR 400 MHz (CDCl3) deltappm: 2.52 (3H, s, CH3), 7.61 (IH, dd, J = 2 Hz and J = 9.1 Hz, CH), 7.67 (IH, dd, J = 2 Hz and J = 9.6 Hz, CH), 7.79 (IH, dd, J = 6.5 Hz and J = 8.6 Hz, CH), 8.56 (IH, 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.Intermediate 84 2-Fluoro-4-(5-methyl-lH-l,2,4-triazol-l-yl)ben?onitrile. White crystals (ethyl acetate-hexane); mp 89-90 C, 1HNMR 400 MHz (CDCl3) delta ppm: 2.69 (3H, s, CH3), 7.49-7.55 (2H, m, 2 x CH), 7.83 (IH, dd, J = 6.8 Hz and J = 8.8 Hz, CH), 8.00 (IH, s, CH). Anal. Calcd for Ci0H7FN4: C 59.40, H 3.49, N 27.71; Found: C 59.17, H 3.22, N 28.01.

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; BRISTOL-MYERS SQUIBB COMPANY; WO2007/64316; (2007); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics

Some common heterocyclic compound, 22300-52-3, name is 4,5-Dibromo-2H-1,2,3-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. COA of Formula: C2HBr2N3

To a solution of4,5-dibromo-2H-1,2,3-triazole (1500 mg, 6.6 mmol) in DMF (12 mL) at -20 ¡ãCwere added iodomethane-d3 (0.82 ml, 13.2 mmol) and potassium carbonate (1736.2 mg, 12.6 mmol). The reaction mixture was allowed to warm up to rt and stirred over 3 days. The reaction mixture was treated with water and extracted with EtOAc. The organic phase was dried over MgSO4, filtered, concentrateddown and purified by silica gel column chromatography, eluting byEtOAc/hexnaes, to give the product (376 mg, 23percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22300-52-3, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; CAI, Zhenhong R.; CHO, Aesop; BUENROSTRO, Ana Zurisadai Gonzalez; HAN, Xiaochun; JABRI, Salman Y.; MCFADDEN, Ryan; QI, Yingmei; VOIGT, Johannes; YANG, Hong; XU, Jie; XU, Lianhong; (545 pag.)WO2019/75291; (2019); A1;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics