Month: March 2021

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. 21524-39-0, name is 2,3-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2,3-Difluorobenzonitrile

General procedure: To a soln. of C-5 (1 eq) in DMSO (1.5 mL/mmol) was added K2CO3 (2 eq) and BB-8 (1.2 eq). The rxn mixture was heated at a given temperature for a given time (see Table 44) and was partitioned between DCM and water. The org. phase was washed with water (3x) and with brine, dried over MgSCh and concentrated in vacuo. The crude was purified by CC using EtOAc/MeOH.2,

The synthetic route of 21524-39-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (188 pag.)WO2019/141803; (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. 78881-21-7, name is 4-Amino-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H8N2

In a round-bottomed flask 4-amino-3-methylbenzonitrile (Alfa Aesar; 10.88 g, 82 mmol), and Et3N (22.95 mL, 165 mmol) were stirred in DCM (200 mL) at 0C. TFAA (13.95 mL, 99 mmol) was added slowly via a dropping funnel and the mixture stirred at room temperature for 30 min. The reaction mixture was poured into 2M HCI (150 mL). The organic layer was then collected and then washed with a saturated solution of sodium bicarbonate (150 mL), dried (MgSC^), filtered and the solvent was removed to give a dark yellow solid (19.37 g);m/z (ES”) 227 (M-1 ); H NMR (400 MHz, CDCI3): delta 8.43 (1 H, d), 7.91 (1 H, bs), 7.59 (1 H, dd), 7.56 (1 H, s), 2.37 (3H, s).

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 78881-21-7.

Reference:
Patent; PROXIMAGEN LIMITED; DINNELL, Kevin; LIGHTFOOT, Andrew; MORTON, Gillian Elizabeth; WO2011/45353; (2011); 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. 263159-64-4, name is 2-Bromo-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H6BrN

To a solution of 2-bromo-3-methylbenzonitrile (12 g, 51 mmol, 1.0 eq) in tetrachloromethane (127.5mL) was added N-bromosuccinimide (10 g, 56.1 mmol, 1.1 eq) and Bz2O2 (0.075 g, 0.31 mmol, 0.006 eq) at r.t. The reaction flask was vacuumed and backfilled by nitrogen. The reaction was stirred at reflux overnight. The reaction was cooled and stirred at r.t. Insoluble matter was removed by filtration. The filtrate was cooled with ice-water, and then filtered to give 2-bromo-3- (bromomethyl)benzonitrile (7.6 g, yield 54%): Purity by IH-NMR: 90%.

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 263159-64-4.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; ZHOU, Huchen; DING, Dazhong; ZHOU, Yasheen; ZHANG, Yong-Kang; PLATTNER, Jacob J.; WO2011/22337; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 606080-43-7,Some common heterocyclic compound, 606080-43-7, name is Methyl 2-cyano-5-fluorobenzoate, molecular formula is C9H6FNO2, 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.

A mixture of methyl 2-cyano-5-fluorobenzoate (11.2 g, 62.5 mmol), tert-butyl piperazine-1-carboxylate (15.1 g, 81.3 mmol) and potassium carbonate (9.50 g, 68.8 mmol) in DMSO (130 mL) was stirred at room temperature for 1 day. The mixture was diluted with water and precipitates formed were collected by filtration, washed with water and was dissolved in a mixture of ethyl acetate and methanol. The solution was washed with water and concentrated in vacuo. The residue was crystallized from ethyl acetate-hexane to give 13 (9.89 g, 46%). 1H NMR (CDCl3) delta 1.49 (s, 9H), 3.363.39 (m, 4H), 3.593.61 (m, 4H), 3.99 (s, 3H), 6.99 (dd, J = 2.7 Hz, 8.8 Hz, 1H), 7.54 (d, J = 2.7 Hz, 1H), 7.63 (d, J = 8.8 Hz, 1H). Anal. Calcd for C18H23N3O4: C, 62.59; H, 6.71; N, 12.17. Found: C, 62.52; H, 6.57; N, 12.11.

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

Reference:
Article; Yamashita, Tohru; Kamata, Makoto; Endo, Satoshi; Yamamoto, Mitsuo; Kakegawa, Keiko; Watanabe, Hiroyuki; Miwa, Katsuhiko; Yamano, Toru; Funata, Masaaki; Sakamoto, Jyun-Ichi; Tani, Akiyoshi; Mol, Clifford D.; Zou, Hua; Dougan, Douglas R.; Sang, BiChing; Snell, Gyorgy; Fukatsu, Kohji; Bioorganic and Medicinal Chemistry Letters; vol. 21; 21; (2011); p. 6314 – 6318;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 63069-50-1, A common heterocyclic compound, 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, molecular formula is C7H5FN2, 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.

General procedure: To the solution of 19 chloro-6, 7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (0.22mmol) and substituted anilines (0.22mmol) in 46 1,4-dioxane (2mL) was added 47 Pd2(dba)3 (0.05mmol), X-Phos (0.05mmol) and 48 Cs2CO3 (0.55mmol). The reaction was heated to reflux under nitrogen gas for overnight. Then the mixture was diluted with ethyl acetate, washed with brine, dried over MgSO4, and evaporated. The residue was purified by column chromatography to give the 20 product. 4.1.8 50 tert-butyl 4-((2-((4-(methylsulfonyl)phenyl)amino)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (12)

The synthetic route of 63069-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fang, Yuanying; Xiong, Lijuan; Hu, Jianguo; Zhang, Shaokun; Xie, Saisai; Tu, Liangxing; Wan, Yang; Jin, Yi; Li, Xiang; Hu, Shaojie; Yang, Zunhua; Bioorganic Chemistry; vol. 86; (2019); p. 103 – 111;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 114344-60-4, A common heterocyclic compound, 114344-60-4, name is 2-Amino-3-bromobenzonitrile, molecular formula is C7H5BrN2, 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.

General procedure: 9-Amino-4-X-5-bromo-2-(alkyl)-2,3-dihydropyrrolo[3,4-b]quinolin-1-one (X = H or F).A white slurry of 4-X-3-bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (1.0 equiv) in t-butanol (0.08-1.00 M) was warmed to 45 C and treated with sodium t-butoxide (1.2 equiv). The resulting green solution was heated at 45 C for 3 h. The reaction was cooled to room temperature, partitioned between methylene chloride and water and the organic layer was washed with saturated aqueous sodium bicarbonate and the combined aqueous layers were extracted with methylene chloride. The organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give a light tan solid in greater than 80% yield, which was used without further purification.The intermediate compounds were prepared as follows:4-X-3-Bromo-2-[1-(alkyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzonitrile (X = H or F).2-Amino-3-bromo-4-X-benzonitrile (1.0 equiv) and 1-(alkyl)-4-methoxy-1H-pyrrol-2(5H)-one (2.0 equiv) were combined in acetic acid (0.5-0.8 M benzonitrile in HOAc) and heated to 80 C. Methanesulfonic acid (2.5 equiv) was dissolved in acetic acid (10 M) and added dropwise via syringe over 15 min. The reaction was stirred for 1 h at 80 C and then cooled to rt and placed on a rotary evaporator under high vacuum for 15 min at 55 C to remove the acetic acid. The resulting oil was dissolved in methylene chloride and slowly added dropwise over 20 min to a solution of saturated aqueous sodium bicarbonate at 0-5 C, maintaining the pH value above 8. The resultant precipitate from the biphasic system was separated, washed with water twice and then with hexane once, and was dried at 50 C under high-vacuum to give a tan solid as the title compound in 70-85% yield, which was used without further purification (see Table 8).

The synthetic route of 114344-60-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 4,4-Dimethyl-3-oxopentanenitrile

General procedure: A microwave tube was charged with ketonitrile (2.0 mmol), methanol (1 mL), and hydrazine monohydrate (2.6 mmol) and subjected to microwave irradiation (100 W, 150 C) for 5 minutes. Volatiles were subsequently removed under reduced pressure. The residue was purified by either trituration with cold methanol or cyclohexane, or by using column chromatography to give the final product.

The synthetic route of 59997-51-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kelada, Mark; Walsh, John M. D.; Devine, Robert W.; McArdle, Patrick; Stephens, John C.; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 122 – 1228;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 623-03-0, name is 4-Chlorobenzonitrile, molecular formula is C7H4ClN, 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. Product Details of 623-03-0

The reaction substrate o-aminothiophenol (0.318 mL, 3 mmol) was accurately measured,P-chlorobenzonitrile (0.412 g, 3 mmol),Methanesulfonic acid (0.0028 g, 0.03 mmol),Followed by addition to a 25 mL Schlenk flask,And the mixture was allowed to stand in an oil bath at 40 C for 14 h.After the reaction was stopped, the mixture was extracted with water and ethyl acetate as an extractant,The extracted organic phase was dried with anhydrous Na2SO4 for 2 h,After removal of the solvent by rotary evaporation,To give the crude target product 2- (4-chloroaryl) benzothiazole.Followed by recrystallization step:The crude 2- (4-chloroaryl) benzothiazole was placed in a 50 mL flask.The flask was placed in a heating jacket and heated to 50 C,Slowly dropping anhydrous ethanol to its complete dissolution,The flask was then removed from the heating jacket and allowed to stand at room temperature for 4 h,To be white crystal precipitation after the full use of filter paper filter,To give the desired product 2- (4-chloroaryl) benzothiazole,The yield was 97%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 623-03-0, its application will become more common.

Reference:
Patent; Dalian University of Technology; Yu Xiaoqiang; Bao Ming; Feng Xiujuan; Pu Zichao; (10 pag.)CN104910098; (2017); B;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 94088-46-7, name is 2-Fluoro-6-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Safety of 2-Fluoro-6-methoxybenzonitrile

General procedure: A mixture of benzonitrile 1 (10.0 mmol) and methylhydrazine (2.8 mL, 50.0 mmol) in EtOH (10.0 mL) was heated to reflux overnight. The mixture was cooled to rt and then concentrated. H2O (10.0 mL) and EtOAc (20.0 mL) were added to the residue. The organic layer was washed with H2O (10.0 mL), brine (10.0 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to silica-gel chromatography by using EtOAc/hexanes (1:1) as eluent to give the product 2.

The synthetic route of 94088-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Han-Jun; Hung, Shiang-Fu; Chen, Chuan-Lin; Lin, Mei-Huey; Tetrahedron; vol. 69; 19; (2013); p. 3907 – 3912;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 67515-59-7, 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. 67515-59-7 name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, 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.

General procedure: 4-fluoro-3-(trifluoromethyl)benzonitrile (1 equiv) and the alcohol (1 equiv) were added to a microwave vial and cooled in an ice bath, then 0.5M potassium tert-butoxide in tetrahydrofuran (1.1 equiv) was carefully added and allowed to warm to room temperature. The contents were then heated to 1 15 C for 1 minute in the microwave. After cooling, celite was added and the solvent was removed under reduced pressure. The resulting powder was subjected to flash chromatography on silica gel.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-3-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; THORPE, Steven Brandon; SANTOS, Webster L.; LYNCH, Kevin R.; (375 pag.)WO2017/172989; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts