Category: 1072-68-0

Synthetic Route of 1072-68-0, The chemical industry reduces the impact on the environment during synthesis 1072-68-0, name is 1,4-Dimethylpyrazole, I believe this compound will play a more active role in future production and life.

After phase separation, the organic phase was distilled to afford 170.1 g (1.3 mol) of 5-chloro-1,4-dimethylpyrazole of boiling point (120) 105 C. and a purity of 99.7% (GC) and 99.3 g (0.6 mol) of 3,5-dichloro-1,4-dimethylpyrazole of boiling point (15) 85 C. and a purity of 99.5% (GC). The yields of 5-chloro-1,4-dimethylpyrazole and 3,5-dichloro-1,4-dimethylpyrazole resulted in an overall yield of 95% based on 1,4-dimethylpyrazole.

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, 1,4-Dimethylpyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merkle, Hans Rupert; Fretschner, Erich; US2004/102505; (2004); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1072-68-0,Some common heterocyclic compound, 1072-68-0, name is 1,4-Dimethylpyrazole, molecular formula is C5H8N2, 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 1,4-dimethyl-pyrazole (10 g, 104.03 mmol) in DMF (150 mL) was added NIS (21.06 g, 93.63 mmol) in one portion at 25 C under ?. The mixture was stirred at 60 C for 12 h. The mixture was poured into ice-water (300 mL) and stirred for 5 min. The aqueous phase was extracted with MTBE (3 chi 300 mL). The combined organic phase was washed with brine (3 chi 200 mL), dried over anhydrous Na2SO/j, filtered and concentrated under reduced pre ssure . The re sidue was purified by silica gel column chromatography (PE : EtO Ac= 10 : 1 – 1 : 1 ) to give 3-iodo- 1,4-dimethyl-pyrazole as a brown solid. lH NMR (400 MHz, CDC33): delta ppm 7.05 (s, 1 H), 3.86 (s. 3 1 1). 1.98 (s, 3H).

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

Reference:
Patent; DENALI THERAPEUTICS INC.; ESTRADA, Anthony A.; FENG, Jianwen A.; LYSSIKATOS, Joseph P.; SWEENEY, Zachary K.; DE VICENTE FIDALGO, Javier; (271 pag.)WO2017/87905; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – 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. 1072-68-0, name is 1,4-Dimethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C5H8N2

1,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole A solution of 1,4-dimethyl-1H-pyrazole (480.0 mg, 4.993 mol) in tetrahydrofuran (20 mL, 300 mmol) at 0 C. was added 1.6 M n-butyllithium in hexane (4.7 mL, 7.5 mmol). The solution was stirred at room temperature for 1 h and then cooled to -78 C. To the solution was added 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.63 mL, 7.99 mmol). The reaction mixture was stirred at -78 C. for 0.5 h, then warmed up to 0 C. (taking 0.5 h). The reaction was quenched with brine and extracted with EtOAc (3*). The combined organic phases were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by combi-flash chromatography and eluted with EtOAc/hexane (0-60%). The purification gave 142 mg of product as white solid.

The synthetic route of 1072-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Huang, Taisheng; Feng, Hao; Kong, Lingquan; Wang, Anlai; Ye, Hai Fen; US2013/96144; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1072-68-0, A common heterocyclic compound, 1072-68-0, name is 1,4-Dimethylpyrazole, molecular formula is C5H8N2, 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.

Sodium hydride (60% dispersion in mineral oil, 0.35 g, 8.65 mmol) was suspended in 12 ml tetrahydrofuran. A solution of 4-methyl-1 H-pyrazole (0.60 g, 7.3 mmol) in 2 ml tetrahydrofuran was added dropwise and the mixture was stirred for 1 h at room temperature. Methyl iodide (0.45 ml, 7.23 mmol) was added drop-wise and the mixture was stirred overnight forming a precipitate. The mixture was filtered and the solid was washed with a little tetrahydrofuran and the filtrates combined to give a crude solution of 1 ,4-dimethyl-1 H-pyrazole. The crude solution was cooled in an ice-bath under nitrogen and n-butyl lithium (1 .6 M in hexanes, 3.70 ml, 5.92 mmol) was added drop-wise with stirring over 15 min. After addition, the mixture was stirred at room temperature for 2 h. The mixture was then cooled to -78 C and a solution of 2-bromo-5-(trifluoromethyl)benzaldehyde (1 .49 g, 5.89 mmol) in 2 ml tetrahydrofuran was added over 1 min. The mixture was stirred overnight, warming to room temperature. The solution was partitioned between saturated aqueous ammonium chloride solution and ethyl acetate. The organic extract was washed with brine, dried over magnesium sulphate, filtered and evaporated. The residue was purified using the Isolera purification system (ethyl acetate-hexanes gradient, 0:100 rising to 100:0) to give 710 mg (2.03 mmol, 41 %) of the title compound as a white solid. Purity 96%. 1H NMR (300 MHz, DMSO-d6) delta ppm 8.13 (d, 1 H, J = 2.3 Hz), 7.86 (d, 1 H, J = 8.2 Hz), 7.66 (dd, 1 H, J = 8.2, 2.3 Hz), 7.08 (s, 1 H), 6.51 (d, 1 H, J = 5.3 Hz), 5.93 (d, 1 H, J = 4.7 Hz), 3.83 (s, 3H), 1.42 (s, 3H). UPLC/MS (3 min) retention time 1 .72 min. LRMS: m/z 349, 351 (M+1 ).

The synthetic route of 1072-68-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL, S.A.; EASTWOOD, Paul Robert; GOMEZ CASTILLO, Elena; GONZALEZ RODRIGUEZ, Jacob; LOZOYA TORIBIO, Maria Estrella; MATASSA, Victor Giulio; MIR CEPEDA, Marta; ROBERTS, Richard Spurring; VIDAL JUAN, Bernat; WO2013/10881; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1072-68-0, 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. 1072-68-0, name is 1,4-Dimethylpyrazole belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 7: 1,4-Dimethyl-1H-pyrazole-5-sulfonyl chlorideA solution of 23% n-butyl lithium in hexane (17.3 mL, 1.2 eq) was added drop-wise to a solution of 1,4-dimethyl-1H-pyrazole (5 g, 1 eq.) in dry ether (50 mL) at -65 C. under a nitrogen atmosphere. The temperature of the resulting suspension was raised to 0 C. temperature over 1 hour and then cooled to -70 C. Excess sulfur dioxide was bubbled to the mixture for 30 minutes, while maintaining the temperature below -65 C. The solution was stirred at -65 C. for 1 hour and was then allowed to warm to room temperature. The resulting precipitate was filtered, washed with ether and dried to yield the lithium sulfinate salt of 1,4-dimethyl-1H-pyrazole. [0570] 1H NMR (400 MHz, DMSO-d6) delta ppm 2.03 (s, 3H) 3.87 (s, 3H) 6.94 (s, 1H)

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

Reference:
Patent; Carroll, Colm; Goldby, Anne; Teall, Martin; US2013/324576; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 1072-68-0, name is 1,4-Dimethylpyrazole, belongs to pyrazoles-derivatives 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 1072-68-0, Recommanded Product: 1072-68-0

PREPARATION 129 (2-Bromo-5-fluorophenyl)(1 ,4-dimethyl-1 H-pyrazol-5-yl)methanol Sodium hydride (60% dispersion in mineral oil, 0.35 g, 8.65 mmol) was suspended in 12 ml tetrahydrofuran. A solution of 4-methyl-1 H-pyrazole (0.60 g, 7.3 mmol) in 2 ml tetrahydrofuran was added dropwise and the mixture was stirred for 1 h at room temperature. Methyl iodide (0.45 ml, 7.23 mmol) was added drop-wise and the mixture was stirred overnight forming a precipitate. The mixture was filtered and the solid was washed with a little tetrahydrofuran. The filtrates combined to give a crude solution of 1 ,4-dimethyl-1 H-pyrazole. The crude solution was cooled in an ice-bath and n-butyl lithium (1 .6 M in hexanes, 5.40 ml, 8.64 mmol) was added dropwise with stirring over 15 min under a nitrogen atmosphere. The cooling bath was removed and the mixture was stirred at ambient temperature for 2 h. The mixture was cooled to -78 C and a solution of 2-bromo-5- fluorobenzaldehyde (1 .76 g, 8.67 mmol) in 3 ml tetrahydrofuran was added over 1 min. The mixture was stirred overnight, warming to room temperature. The mixture was partitioned between saturated aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulphate, filtered and evaporated. The residue was purified using the Isolera purification system (ethyl acetate-hexane gradient, 0: 100 rising to 100:0) to give 720 mg (2.41 mmol, 33%) of the title compound as a white solid. Purity 100%. 1 H N MR (300 MHz, CHLOROFORM-d) delta ppm 7.45-7.54 (m, 2H), 7.19 (s, 1 H), 6.91 -6.98 (m, 1 H), 6.04 (s, 1 H), 3.84 (s, 3H), 2.70 (br s, 1 H), 1 .75 (s, 3H). UPLC/MS (3 min) retention time 1 .53 min. LRMS: m/z 299, 301 (M+1 ).

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; ALMIRALL, S.A.; VIDAL JUAN, Bernat; ALONSO DIEZ, Juan Antonio; BUIL ALBERO, Maria Antonia; EASTWOOD, Paul Robert; ESTEVE TRIAS, Cristina; LOZOYA TORIBIO, Maria Estrella; ROBERTS, Richard Spurring; VIDAL GISPERT, Laura; GONZALEZ RODRIGUEZ, Jacob; MIR CEPEDA, Marta; WO2013/10880; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – 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 1072-68-0 as follows. 1072-68-0

To a solution of 1,4-dimethyl-1H-pyrazole (52 g, 541 mmol) in anhydrous THF (1.0 L) was added dropwise n-BuLi (0.22 L, 2.5 M, 550 mmol) at -78 C with stirring over 2 h. Then, a solution of (RS)-4 (110 g, 396 mmol) in anhydrous THF (1.0 L) was added dropwise to the above solution over 1 h at the same temperature. The resulting mixture was stirred at -78 C for 1.5 h. TLC (PE-EtOAc, 1:2) showed (RS)-4 was completely consumed. The mixture was poured into sat. aq NH4Cl (1 L) and extracted with EtOAc (3 ¡Á 0.8 L). The combined organic extracts were washed with brine (1 L), dried (Na2SO4), and concentrated to give the crude product. Purification by column chromatography on silica gel (PE-EtOAc, 20:1 ? 5:1) gave 8i as a yellow oil, and 7i as a yellow solid when the column was continuously eluted with PE-EtOAc(5:1 ? 2:1).

According to the analysis of related databases, 1072-68-0, the application of this compound in the production field has become more and more popular.

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. 1072-68-0, name is 1,4-Dimethylpyrazole, A new synthetic method of this compound is introduced below., 1072-68-0

To a solution of 1,4-dimethyl-1H-pyrazole (2.5 g, 26.0 mmol, 1 equiv) in tetrahydrofuran (50 mL) was added n-butyllithium in hexane solution (2.5 M in hexane, 78.0 mmol, 31 mL, 3 equiv) dropwise at 0 C. under nitrogen atmosphere. The resulting solution was stirred at room temperature for 1 h and then cooled to -78 C. 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (14.52 g, 78.017 mmol, 3 equiv) was added and the reaction mixture was stirred at -78 C. for 0.5 hour, then slowly warmed up to 0 C. The reaction was quenched with brine and extracted with EtOAc (250 mL*3). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1:5). This resulted in 2.6 g (45%) of 1,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole as a white solid.

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.

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. 1072-68-0, name is 1,4-Dimethylpyrazole, A new synthetic method of this compound is introduced below., 1072-68-0

To a solution of 1,4-dimethyl-1H-pyrazole (2.5 g, 26.0 mmol, 1 equiv) in tetrahydrofuran (50 mL) was added n-butyllithium in hexane solution (2.5 M in hexane, 78.0 mmol, 31 mL, 3 equiv) dropwise at 0 C. under nitrogen atmosphere. The resulting solution was stirred at room temperature for 1 h and then cooled to -78 C. 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (14.52 g, 78.017 mmol, 3 equiv) was added and the reaction mixture was stirred at -78 C. for 0.5 hour, then slowly warmed up to 0 C. The reaction was quenched with brine and extracted with EtOAc (250 mL*3). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1:5). This resulted in 2.6 g (45%) of 1,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole as a white solid.

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.