Month: March 2021

Electric Literature of 170572-49-3, 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. 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-fluoro-4-methylbenzonitrile (29.54 g) and NBS (46.7 g) as a suspension in 1,2-dichloroethane (500 ml) was treated with benzoyl peroxide (4.24 g) in a flask mounted with a reflux condenser open to air. The flask was immersed in an oil bath at 75 C and light shun on it with a sunlamp. A more vigorous reflux was suddenly observed and the reaction became homogeneous. The reaction was let stir at this temperature for a total of 2 hours then let cool to room temperature. Hexanes (500 ml) was added and the precipitate filtered and discarded. The filtrate was concentrated under reduced pressure to approximately 100 ml and taken up in ethyl acetate (200 ml). The reaction was washed with half saturated sodium bicarbonate (100 ml), then brine (100 ml). The organic layer was separated and dried over magnesium sulfate. The organic phase was concentrated under reduced pressure to give the benzylic bromide as a yellow solid that was used as such in the next step.

The chemical industry reduces the impact on the environment during synthesis 3-Fluoro-4-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/67797; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 16588-02-6, 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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2-chloro-5-nitrobenzonitrile (2g,1 eq,10.96mmol), potassium carbonate (4.54g, 3eq, 32.7001), piperidine (1 ¡¤ 63 mL, 1.5 eq, 16.34 mmol) and DMF (5 mL) at 90 C Should be 3h, until the reaction is complete, remove the oil bath. DMF was diluted with 100 mL EA, washed with saturated ammonium chloride and sodium chloride respectively. The aqueous phase was extracted again with ethyl acetate. The organic phases were combined and dried over anhydrous sodium sulfate. The filtrate was concentrated to give a yellow solid (Compound 10) 2.528 g, yield 99%

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

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Xu Zhongliang; Wang Heyao; Cai Mengxin; (31 pag.)CN106892871; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 63069-50-1, 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 63069-50-1 as follows.

General procedure: As shown in FIG. 1, the raw material 1 (acidic liquids of aniline) and raw material 2 (NaNO2 aqueous solution with mass concentration of 20%) were fed to temperature section 1 with constant-flow pump, and the diazotization of aniline completed while the materials flowed past the temperature section 1. The raw material 3 (Na2SO3 aqueous solution with mass concentration of 19%) was fed to temperature section 2 with constant-flow pump for preheating, then mixed with diazonium salt formed through temperature section 1 in temperature section 3, flowed through temperature section 3 until the reaction was completed. The reaction solution from temperature section 3 flowed into temperature section 4 after mixed with raw material 4 (acid), and the reaction completed while flow through temperature section 4. The reaction mixture was collected, crystallization by cooling the temperature, after filtration and drying to get the phenylhydrazine salts product. Reaction parameters and results were as follows:

According to the analysis of related databases, 63069-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHANGHAI HYBRID-CHEM TECHNOLOGIES; MA, Bing; Pan, Shuai; (35 pag.)US2019/152896; (2019); 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. 101184-73-0, name is 2-(4-Bromophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 101184-73-0

A suspension of 2-(4-bromophenyl)-2-methylpropanenitrile (110 mg, 0.491 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (187 mg, 0.736 mmol), potassium acetate (72.3 mg, 0.736 mmol) and Pd(dppf)Cl2 (18.0 mg, 0.0250 mmol) in dioxane (3 mL) was degassed and the reaction was heated to 95 C. for 90 minutes. The reaction mixture was concentrated to provide 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile which was used directly in subsequent reactions.

According to the analysis of related databases, 101184-73-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Scientific Systems, Inc.; Cory, Kevin S; Doo, Jimin; Farrand, Julie; Guerrero, Juan A; Katana, Ashley A; Cato, Daryl; Laisaweed, Scott I; Lee, Jiayao; Lingco, John O; Nicolaus, May; Notte, Gregory; Phyen, Hyeoung-Jung; Sangy, Michael; Sumit, Arun C; Adam J, Surayyah; Stephens, Cork L; Venkatraman, Chandrasekar; Watkins, William J; Yang, Jong Yu; Jabloki, Jeff; Jifel, Shiela; Ro, Jennifer; Lee, Sung H; Jao, Chung Dong; Grove, Jeffery; Su, Jianjun; Blomgren, Peter; Mitchell, Scott A; Shyung, Jin Ming; Chandrasekar, Jayaraman; (460 pag.)KR2016/37198; (2016); A;,
Nitrile – Wikipedia,
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Electric Literature of 1080-74-6, 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 1080-74-6 as follows.

A solution of intermediate 67 (135 mg, 0.130 mmol) in chloroform (10 cm3) and pyridine (0.75 cm3) is degassed for 10 minutes with nitrogen. 2-(3- Oxo-indan-1 -ylidene)-malononitrile (180 mg, 0.91 mmol) is added in one portion and the reaction mixture is stirred at 23 C for 150 minutes. Methanol (15 cm3) is added and the obtained precipitate is collected by filtration and washed with methanol (3 x 10 cm3). The solid is filtered through a pad of silica (40-60 petrol:dichloromethane; 2:3). Concentration in vacuo followed by trituration in refluxing acetone (20 cm3) and then in a 3:1 mixture of acetone:chloroform (40 cm3) gives compound 1 15 (144 mg, 79%) as a dark blue powder. 1H NMR (400 MHz, CDCIs) 8.84 (2H, s), 8.61 – 8.67 (2H, m), 7.84 – 7.90 (2H, m), 7.63 – 7.72 (6H, m), 7.13 – 7.21 (8H, m), 6.83 – 6.90 (8H, m), 3.81 (4H, m), 3.72 (4H, m), 1 .78 – 1 .92 (4H, m, J 6.6), 1 .56 (4H, m), 1 .26 (4H, m), 1 .00 (12H, d, J 6.7), 0.94 (12H, t, J 7.5).

According to the analysis of related databases, 1080-74-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; NANSON, Lana; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (327 pag.)WO2018/65350; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 64248-64-2,Some common heterocyclic compound, 64248-64-2, name is 2,5-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

Step A: Thio-Amide Synthesis:1-1 1 -2A stirred solution of the appropriate benzonitrile e.g., 2,5-difluorobenzonitrile (1-1), (15 mmol) in pyridine (10 rnL) was treated with sulfide (20% wt solution in water, 16.5 mmol) and triethyl amine (16.5 mmol). The reaction mixture was stirred at 500C for 5 hr until the reaction was complete. After cooling to RT, the mixture was diluted with cold water. Extracted with EtOAc, and the organics separated, then washed with H2O (x3), sat. brine (x3), then dried (Na2SO4), filtered, and evaporated under reduced pressure to give the crude. Purification on silica gel column (20% ethyl acetate/hexane) to afford thio-amide as yellow solid, 1-2 (yield 88.5%). 1H NMR (300 MHz, CDCl3): delta 7.12 (m, 2 H), 7.90 (br, 2 H), 8.08 (m, 1 H).

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

Reference:
Patent; NOVARTIS AG; WO2008/63912; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 867366-91-4, name is 3-Bromo-5-methoxybenzonitrile, 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 867366-91-4, SDS of cas: 867366-91-4

Step 2 A solution of 3-bromo-5-methoxybenzaldehyde (4.02 g, 18.7 mmol) and hydroxylamine hydrochloride (6.50 g, 93.5 mmol) in pyridine (50 ML) and EtOH (50 ML) was heated to 65 C. for 16 h.The solvent was removed, and the remaining materials were partitioned between 1:1 EtOAc/hexanes (150 ML) and H2O (75 ML).The organic layer was washed with brine (60 ML), and the solvents were evaporated.The remaining oil was dissolved in anhydrous dioxane (50 ML), and trifluoroacetic anhydride (5.1 ML, 37.4 mmol) and pyridine (9.07 ML, 112.2 mmol) were added.The mixture was heated to 60 C. for 3 h and then cooled to RT. CHCl3 (100 ML) was added, and the organic layer was washed with H2O (2*50 ML), 5% aqueous HCl solution (30 ML), brine (30 ML), and dried with anhydrous MgSO4.The solvents were removed to provide a white solid.This solid was placed in a 150 ML flask that was flushed with nitrogen.Collidine (40 ML) and LiI (7.92 g, 59.10 mmol) were added, and the mixture was heated to 180 C. for 5 h.The reaction mixture was cooled to RT, and partitioned between H2O (400 ML) and EtOAc (100 ML).The layers were separated, and the aqueous layer was acidified with 10% aqueous HCl solution, and extracted with 2:1 EtOAc/hexanes (3*125 ML).The combined organic layers were washed with H2O (100 ML), 10% aqueous HCl solution (2*50 ML), brine (75 ML), and dried with anhydrous MgSO4.The solvents were evaporated and the resulting solid was purified by flash chromatography on silica gel (10% to 40% EtOAc/hexanes) to provide 3.40 g (92%) of 3-bromo-5-hydroxybenzonitrile (116)116).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Roche Palo Alto LLC; US2004/198736; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 115279-57-7, 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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

[00336] The synthesis of this monomer proceeds first by synthesis of the Suzuki reaction coupling partner (3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolane)quinolin-6-yl)-N-boc- methanamine starting from methyl 3-bromoquinoline-6-carboxylate. Reduction of the methyl ester with lithium aluminum hydride followed by Mitsunobu reaction with phthalimide and hydrazine cleavage provides the benzylic amine. Protection of the benzylic amine with di- tert-butyl dicarbonate followed by a Miyaura borylation reaction provides (3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolane)quinolin-6-yl)-N-boc-methanamine. (1585) [00337] An SNAr reaction of 2-(4-aminophenyl)-2-methylpropanenitrile with 6-bromo-4- chloro-3-nitroquinoline provides the substituted amino-nitro-pyridine. Reduction of the nitro group with Raney-Ni under a hydrogen atmosphere followed by cyclization with trichloromethyl chloroformate provides the aryl -substituted urea. Substitution of the free N-H of the urea with methyl iodide mediated by tetrabutyl ammonium bromide and sodium hydroxide followed by Suzuki coupling of (3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolane)quinolin-6-yl)-N-boc-methanamine and then Boc-deprotection using TFA produces the TFA salt.

The chemical industry reduces the impact on the environment during synthesis 2-(4-Aminophenyl)-2-methylpropanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; REVOLUTION MEDICINES, INC.; SEMKO, Christopher; PITZEN, Jennifer; WANG, Gang; TIBREWAL, Nidhi; AGGEN, James Bradley; THOTTUMKARA, Arun P.; BURNETT, G. Leslie; GLIEDT, Micah James Evans; KISS, Gert; WON, Walter; LEE, Julie Chu-li; GILL, Adrian Liam; (538 pag.)WO2018/204416; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 1147558-43-7, The chemical industry reduces the impact on the environment during synthesis 1147558-43-7, name is 4-Amino-3-chloro-5-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

3.123.2. Step ii): 4-[[6-[bis[(4-methoxyphenyl)methyl]amino]-4-(methylamino)-5-nitro-2- pyridyl]amino]-3-chloro-5-fluoro-benzonitrtte A mixture of 6-chloro-N2,N2-bis[(4-methoxyphenyl)methyl]-N4-methyl-3-nitro-pyridine-2,4- diamine (3.39 mmol), 4-amino-3-chloro-5-fluoro-benzonitrile (6.78 mmol) and CS2CO3 (13.6 mmol) in DMA (15 mL) is stirred for 16 h at 120 C. A solution of saturated NH4C1 is added to the mixture. The solid is filtered out and further washed with water. The solid is taken up in EtOAc and the organic mixture is washed (H20 and brine), dried (Na2S04) and concentrated. The residue is purified by flash column chromatography (S1O2, 100:0 to 50:50 petroleum ether/EtOAc) to afford the desired product.

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-Amino-3-chloro-5-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; QUINTON, Evelyne; JOANNESSE, Caroline, Martine, Andree-Marie; DE BLIECK, Ann; BLANC, Javier; (263 pag.)WO2017/12647; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 69395-13-7, These common heterocyclic compound, 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, 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.

(ii) t-Butoxycarbonylamino-3-[2-(4-cyanophenyl)ethoxy]-2-methylbenzene Triphenylphosphine (1.31 g, 13.5 mmol) and diethylazodicarboxylate (1.7 mL) were dissolved in THF (20 mL) under nitrogen. After 15 minutes 3-t-butoxycarbonylamino-2-methylphenol (2.48 g; 11.1 mmol; from step (i) above) dissolved in THF (20 mL) and 2-(4-cyanophenyl)ethanol (1.9 g, 13 mmol) were added. After 5 days at room temperature water was added and the stirring continued for 30 minutes. The mixture was extracted with EtOAc. The organic phase was washed with water and brine, dried (MgSO4) and the solvent removed in vacuo. Purification by flash chromatography afforded 2.98 g (77%) of the sub-title compound. 1H NMR (300 MHz; CDCl3): delta7.4-7.8 (m, 5H), 7.10 (m, 1H), 6.63 (dd, 1H), 6.24 (s, 1H), 4.18 (t, 2H), 3.16 (t, 2H), 2.02 (s, 3H), 1.51 (s, 9H)

The synthetic route of 69395-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astra Aktiebolag; US6221898; (2001); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts