Month: February 2021

Synthetic Route of 50846-36-1, A common heterocyclic compound, 50846-36-1, name is 2-Amino-2-methylpropanenitrile hydrochloride, molecular formula is C4H9ClN2, 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.

Triethylamine (93 mL, 683 mmol, 3 equiv) was added to a solution of compound 32 (46 g, 228 mmol, 1 equiv) and HBTU (99 g, 262 mmol, 1.15 equiv) in DMF (690 mL). After stirring at room temperature for 30 minutes, 2-amino-2-methylpropanenitrile hydrochloride (35.7 g, 296 mmol, 1.3 equiv) was added and the reaction mixture was stirred overnight. The solution was poured into water (4 L) (0512) and extracted with ethyl acetate (3 L). The organic layer was separated, washed with saturated brine (2 L) and concentrated under reduced pressure. The crude product which was dissolved in dichloromethane and purified over silica gel (0.7 Kg), eluting with a gradient of 10 to 20% ethyl acetate in heptanes to give 6-bromo-N-(2-cyanopropan-2-yl)picolinamide.

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:
Patent; PLEXXIKON INC.; ZHANG, Chao; WU, Guoxian; SPEVAK, Wayne; GUO, Zuojun; ZHANG, Ying; (138 pag.)WO2018/226846; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 501-00-8, 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 501-00-8 as follows.

Step 1: 2-(3-fluoro-phenyl)-2-methyl-propionitrile Under an argon atmosphere 77 mL (77 mmol) of a 1M lithium bis(trimethylsilyl)amide solution was added dropwise at -70 C. to 5.0 g (37 mmol) (3-fluoro-phenyl)-acetonitrile in 150 mL THF. The mixture was allowed to come up to -50 C. and was then stirred at this temperature for 1 h. Then at -50 C. 4.8 mL (78 mmol) methyl iodide were added. The reaction mixture was heated to RT overnight. The reaction mixture was slowly combined with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was dried on sodium sulphate and evaporated down. Yield: 5.6 g (93% of theory) ESI-MS: m/z=163 (M+H)+

According to the analysis of related databases, 501-00-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; US2011/195954; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

These common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, 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. category: nitriles-buliding-blocks

10% Palladium on carbon (5.06 g) was added under an atmosphere of nitrogen to a chilled (ice- water bath) solution of 2-(3 -methyl- IH-1, 2,4- triazol-l-yl)-5-nitrobertzonitrile (10.9 g, 47.6 mmol) dissolved in methanol (100 mL). The flask was repeated evacuated and flushed with hydrogen gas (double balloon). The resulting mixture was allowed to warm to rt and left to stir for 16 h under the hydrogen atmosphere. Purged with nitrogen gas. Filtered the crude reaction mixture through a short dialomaceous earth (Celite ) plug. Rinsed reaction vessel and plug with methanol. Concentrated filtrate in vacuo. Dried residue on high vacuum overnight to afford 5-amino-2-(3-methyl-lH-l,2,4-triazol-l-yI)benzonitrile (6.59 g, 70 % yield) as a brown solid. LC-MS (M+H)+ 200.0. 1H NMR (500 MHz, DMSO- J6) delta ppm 2.29 – 2.37 (m} 3 H) 5.99 (s, 2 H) 6.94 (dd, J=8.85, 2.44 Hz, 1 H) 7.00 (d, J-2.44 Hz, 1 H) 7.37 (d, J=8.54 Hz, 1 H) 8.69 – 8.81 (m, 1 H).

The synthetic route of 2-Chloro-5-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 41963-20-6, name is 4-Bromo-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6BrN

Step F tert-Butyl 4-(4-cyano-2-methylphenyl)-3,6-dihydropyridine-1(2H)-carboxylate. A mixture of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (0.40 g, 0.0013 mol), 4-bromo-3-methylbenzonitrile (0.30 g, 0.0016 mol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1, 0.063 g, 0.000078 mol) and potassium carbonate (0.54 g, 0.0039 mol) in N,N-dimethylformamide (6.0 mL, 0.077 mol) was stirred under nitrogen at 80 C. overnight. The mixture was diluted with ethyl acetate, washed with water and brine successively, dried and concentrated. The product was purified by CombiFlash using hexane/EtoAc (max. EA 30%) LC-MS: 299.2 (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 41963-20-6.

Reference:
Patent; Burns, David M.; Yao, Wenqing; He, Chunhong; US2005/250789; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 4435-14-7, 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. 4435-14-7, name is 2-Cyclohexylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 0.846 g (8.1 mmol) of hydroxylamine hydrochloride in 1 1 mL of isopropyl alcohol, 1 .499 g (17.8 mmol) of sodium bicarbonate was added. The resulting mixture was stirred at 25 C to 30 C for 10 – 15 min. 1 .0 g (8.1 mmol) of 2- cyclohexylacetonitrile was added and stirred at 80 C to 85 C for 3 – 4 h. After completion of the reaction, the reaction mixture was cooled to 25 C to 30 C, filtered and washed with 2 mL of isopropyl alcohol. The filtrate was collected and distilled out completely to obtain a crude residue. The residue was chased with 5 mL of toluene to yield the title compound.Yield: 0.6 g (47 %).

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, 2-Cyclohexylacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PIRAMAL LIFE SCIENCES LIMITED; SIVAKUMAR, Meenakshi; JOSHI, Kalpana Sanjay; AWARE, Valmik Sopan; SARDE, Ankush Gangaram; BAGUL, Sandeep Mukunda; MANOHAR, Sonal Mohan; WO2011/104680; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 160892-07-9, 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. 160892-07-9 name is 5-Bromoisophthalonitrile, 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.

5-bromoisophthalonitrile (1 g, 48.3 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolo[3,2,1-jk]carbazole (1.77 g, 48.3 mmol) were dissolved in 1,4dioxane (50 ml). K2CO3 (1.34 g, 96.6 mmol) was dissolved in water and poured into the mixture. The reaction mixture was stirred with N2 bubbling for 30 min and refluxed overnight. After cooling to room temperature, the mixture was filtered and diluted with methylene chloride and washed with distilled water. The organic layer was dried over anhydrous MgSO4 and evaporated in vacuum. And then, the product was isolated by column chromatography on a silica gel.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromoisophthalonitrile, and friends who are interested can also refer to it.

Reference:
Patent; RESEARCH & BUSINESS FOUNDATION SUNGKYUNKWAN UNIVERSITY; LEE, Junyeob; IM, Yirang; (37 pag.)US2018/114924; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 89642-49-9, These common heterocyclic compound, 89642-49-9, name is 4-Bromo-3-nitrobenzonitrile, 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.

15.18 g (52.85 mmol) of 9-phenyl-9H-carbazole-3-yl-boronic acid, 10 g (44.04 mmol) of 4-bromo-3-nitrobenzonitrile, and 0.05 percent by weight (wt %) of a palladium catalyst were dissolved in 25 ml of toluene, 25 ml of 2 molar (M) potassium carbonate was added thereto, and the resulting reaction solution was stirred for 24 hours. After completing the reaction, the resulting reaction solution was extracted using chloroform to remove a solvent therefrom. Then, the resulting solid product was dried. 3 equivalents of triphenylphosphine were added thereto, and the mixture was stirred in dichlorobenzene for 12 hours at a temperature of 160 C. After completing the reaction, 100 ml of methanol was slowly added to the mixture, to thereby filter the resulting reaction solution. The filtered crude product obtained therefrom was dried and purified by column chromatography with a mixture of dichloromethane and hexane as an eluent, thereby obtaining 4.87 g (yield: 31%) of Intermediate 4. The structure of the synthesized compound was identified using a MALDI-TOF mass spectrometer. (0347) MALDI-TOF (calculated: 357.1 g/mol, measured: [M+H]+=358 g/mol)

Statistics shows that 4-Bromo-3-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 89642-49-9.

Reference:
Patent; SAMSUNG ELECTRONICS CO., LTD.; SAMSUNG SDI CO., LTD.; Jeon, Soonok; Numata, Masaki; Lee, Saeyoun; Miyazaki, Hiroshi; Son, Jhunmo; Sim, Myungsun; Lee, Namheon; Ihn, Sooghang; (116 pag.)US10510966; (2019); B2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, belongs to nitriles-buliding-blocks 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 1080-74-6, SDS of cas: 1080-74-6

General procedure: Compound T-TT-CHO (200 mg, 0.2 mmol), INCN (246 mg, 1.2 mmol), and chloroform (30 mL) were added into a 100 mL round bottom flask. After stirred for 10 min under argon protection, pyridine (1 mL) was added by injection and the mixture was stirred at 70C for 6 h. Then methanol (100 mL) was added and the precipitate was collected by filtration after removing the chloroform under reduced pressure. The residue was purified by column chromatography using chloroform as an eluent to give a blue-black powder (226 mg, 84.0%).

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:
Article; Cheng, Qing; Cong, Zhiyuan; Gao, Chao; Liu, Jianqun; Liu, Shengna; Pan, Hui; Wang, Weiping; Wu, Haimei; Zhao, Baofeng; Dyes and Pigments; vol. 178; (2020);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 114772-53-1, The chemical industry reduces the impact on the environment during synthesis 114772-53-1, name is 4′-Methyl-[1,1′-biphenyl]-2-carbonitrile, I believe this compound will play a more active role in future production and life.

To the glass reactor, 4′-methyl-2-cyanobiphenyl was added5.00 kg, and methanol: 10.00 kgWith stirring2. 07 kg of sodium hydroxide,0.94 kgwaterSolubleliquid,Heated to 80 C, the reaction 10 hours,TLC test (developing solvent = petroleum ether: ethyl acetate = 1: 1), the reaction finished cooling to 40 C, and stirring 20 to 30 minutes, then add hydrochloric acid pH = 2 or so, stirring 30 minutes after the re-test pH , No change will continue to cool down to room temperature, some solid precipitation, continue stirring for two hours, centrifugal, washed to neutral, the product is dry 10 ~ 12 hours, the product 5. 30kg, yield 91. 06%Melting point 146 ~ 148 C, purity 99. 12%.

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, 4′-Methyl-[1,1′-biphenyl]-2-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; weite hunan pharmaceutical co ltd; He, liang; Luo, hui; Mo, wei; (10 pag.)CN105399627; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, belongs to nitriles-buliding-blocks 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 658-99-1, Computed Properties of C8H5F2N

2-(3,4-difluorophenyl)acetonitrile (7.730 g, 50.480 mmol) in N,N-dimethylformamide (50 mL) at 0 C and sodium hydride (60.00%, 5.047 g, 126.200 mmol) was added and stirred at the same temperature for 30 minutes. To the reaction mixture 1,3-dibromopropane (10.191 g, 50.480 mmol) was added and further stirred at room temperature for 12 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was purified by column chromatography (SiO2, 40 g cartridge; ethyl acetate / hexane = 0% to 20%) and concentrated to give the title compound (5.100 g, 52.3%) as a colorless oil.

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; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts