Month: June 2021

Application of 53312-80-4,Some common heterocyclic compound, 53312-80-4, name is 4-Amino-2-fluorobenzonitrile, molecular formula is C7H5FN2, 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.

4-Amino-2-fluoro-benzonitrile (610 mg, 4.4 mmol) and trans-4-aminocyclohexanol (2.5 g, 22 mmol) are combined in a 40 mL EPA vial under nitrogen and heated at 150 C. overnight. This reaction mixture is partitioned between ethyl acetate (100 mL) and water (40 mL). The aqueous layer is extracted with more ethyl acetate (50 mL) and the combined organic layers washed with brine (50 mL), dried (MgSO4), concentrated and chromatographed (25 mm, 40 to 100% EtOAc in hexanes) to give starting material (200 mg) and product, 4-Amino-2-(4-hydroxy-cyclohexylamino)-benzonitrile (620 mg, 60%, 90% based on recovered starting material), both as white crystalline solids. (LC/MS m/z=232 [M+H]+)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Amino-2-fluorobenzonitrile, its application will become more common.

Reference:
Patent; Huang, Kenneth He; Hughes, Philip; Ma, Wei; Ommen, Andy; Woodward, Angela; Veal, James; Barta, Thomas; US2008/76813; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 1000339-52-5, 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. 1000339-52-5 name is 3-Fluoro-2-nitrobenzonitrile, 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.

Synthesis of 3-([1,1?-biphenyl]-3-ylamino)-2-nitrobenzonitrile Biphenylamine (4.6 g, 27 mmol) and 3-fluoro-2-nitrobenzonitrile (5.0 g, 30.1 mmol) was added into THF (20 mL) and N,N-diisopropylethylamine (20 mL) and heated at 85 C. for 2 days. The solvent was then evaporated and the residue was then purified by column chromatography using THF:hexane (1:4, v/v) as the eluent. 7.0 g (82% yield) of a red solid was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Fluoro-2-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Universal Display Corporation; KWONG, Raymond; LAM, Sze Kui; LAM, Siu Tung; TSANG, Kit Yee; LEE, Chi Hang; SZIGETHY, Geza; (159 pag.)US2016/218303; (2016); A1;,
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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, A new synthetic method of this compound is introduced below., name: 4-Cyano-3-trifluoromethylaniline

General procedure: A substituted aniline (5.0 mmol) and triethylamine (1.87 g,18.5 mmol) were dissolved by dichloromethane (10 mL),and stirred under an ice-water bath, to which chloroacetylchloride (1.29 g, 11.5 mmol) was added dropwise. Afteraddition, the reaction mixture was stirred for one more hourat room temperature, then EA (30 mL) and H2O (30 mL)were added for an extraction. The organic contract waswashed with water (15 mL × 3) and saturated brine (15 mL),dried over Na2SO4 and evaporated under reduced pressureto afford intermediate 5.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dong, Junze; Zhang, Jingya; Li, Zilu; Asnake, Solomon; Zhang, Daoguang; Olsson, Per-Erik; Zhao, Guisen; Medicinal Chemistry Research; vol. 28; 3; (2019); p. 380 – 386;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, 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.

Weigh 97 mg (0.9 mmol)Diaminamethylene nitrile and247 mg (0.7 mmol)The compound 2 obtained in Example 1 was dissolved in 20 mL of ethanol,After adding 5 drops of acetic acid, the mixture was stirred at room temperature for 2 h. The crude product was recrystallized from ethanol,And purified by column chromatography (eluent: petroleum ether / dichloromethane = 2: 1)The resulting product was finally 250 mg in a yield of 82.1percent.

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

Reference:
Patent; Jiangsu University; Gu Lei; Wu Jiacong; Xia Jinchen; Li Yuanyuan; Han Juan; Wang Yun; Ni Liang; (15 pag.)CN106518900; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 124289-21-0, name is 3-Bromo-5-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-Bromo-5-methylbenzonitrile

3-Bromo-5-hydroxymethylbenzonitrile(4); 3-Bromo-5-methylbenzonitrile(15g, 76 5mmol) was refluxed with N-bromo succiotaniotamiotade(13 6g, 76 5mmol) and benzoyl peroxiotade(925mg, 3 8mmol) in CCI4(I OOmI) under a light of 500W tungsten lamp After 4hr the mixture was cooled to room temperature, filtered, and concentrated The residue was stirred with sodium acetate(9 41 g, 115mmot) in DMF(100ml) for overnight at room temperature The mixture was diluted with ether, washed with water three times, dried with MgSO4, filtered, and evaporated in vacuo The residue was stirred with ammonium hydroxiotade(30ml) in methanol(IOOml) at room temperature After 3hr , the mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography(eluent, ethyl acetate hexane(1 4)) to afford 7 1g(44% overali) of the title compound as a white solid m p 108-109 0C1H-NMR(200MHz, CDCI3) delta 2 03(1 H, t, J=5 6Hz), 4 73(2H, d, J=5 6Hz), 7 60(1 H1 s), 7 70(1 H, s), 7 76(1 H, s) m/z (El) 212 (M+)

The synthetic route of 124289-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY; KIM, Choung, U.; MITCHELL, Michael, L.; SON, Jong, Chan; WO2010/9047; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 60710-80-7,Some common heterocyclic compound, 60710-80-7, name is 3-Amino-4-methylbenzonitrile, molecular formula is C8H8N2, 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 intermediate 7R (231 g, 0.556 mol) in 1,4-dioxane (2.3 L), ptoluenesulfonic acid monohydrate (179 g, 0.95 mol) and 3-amino-4-methylbenzonitrile (110 g, 0.83 mol) were added, purged three times with N2 and stirred at 95 C for 12 h. Then, the reaction mixture was cooled down to 20 C, and a solution of NaHCO3 was added to neutralize the mixture. The precipitated solid formed was filtrated andcombined with another precipitate coming from a reaction performed on 179 g of intermediate 7R. The resulting solid was dissolved in Me-THF (5 L), washed with water three times (3 x 5 L). A silanethiol resin [from Shanghai Meryer CO.,LTD] (60 g) was added to the mixture and reflux for 1.5 h. Then, the resulting mixture was filtered through a pad of celite and concentrated under vacuum. The residue wassuspended in EtOH (5L) overnight, filtered and dissolved in THF (3L). Methyl ten?butylether (6 L) was added to THF and the solid was precipitated, filtered and dried to afford 243g of compound 1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Amino-4-methylbenzonitrile, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier Alexis Georges; PONCELET, Virginie Sophie; GROSS, Gerhard Max; JACOBY, Edgar; MEERPOEL, Lieven; KULAGOWSKI, Janusz Jozef; MACLEOD, Calum; MANN, Samuel Edward; GREEN, Simon Richard; HYND, George; (477 pag.)WO2017/125530; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 34662-29-8, These common heterocyclic compound, 34662-29-8, name is 3-Chloro-4-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.

A mixture of 3-chloro-4-nitrobenzonitrile (620 mg, 2.4 mmol, Chem. Pharm. Bull, (1992) 2399-2404), 1,1-carbonyldiimidazole (778 mg, 4.8 mmol) in tetrahydrofurane (30 ml) was stirred at room temperature overnight. To the mixture was added water (30 ml) and the whole was extracted with ethyl acetate (100 ml×2). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=1/1 as eluent) to afford the titled compound as a white solid (415 mg, 65%). [0455] 1H-NMR (CDCl3) delta:10.96 (s, 1H), 7.17-7.30 (m, 2H), 7.05 (d, J=8.1 Hz, 1H), 6.89 (d, J=1.3 Hz, 1), 4.07 (t, J=7.0 Hz), 3.02 (t, J=7.0 Hz, 2H) ppm.

Statistics shows that 3-Chloro-4-nitrobenzonitrile is playing an increasingly important role. we look forward to future research findings about 34662-29-8.

Reference:
Patent; Ando, Kazuo; Kawai, Makoto; Kawamura, Mitsuhiro; Matsumizu, Miyako; Morita, Asato; Sakurada, Isao; US2004/204409; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 60899-34-5, 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 60899-34-5 as follows.

In a 25 mL single-necked flask, 2,3-dihydro-1-oxo-1H-indene-4-carbonitrile (1.57 g), tetraisopropyl titanate (2.74 g), and S-phenylethylamine (1.45 g), toluene (15 mL), and stirred with heating to 100 C; After the reaction was completed, the temperature of the system was lowered to below 35 C, and an aqueous solution (20 mL) of sodium hydroxide (0.48 g) was added, and the filtrate was collected by stirring and filtration. The filtrate was concentrated to obtain 2.3 g of (S,Z)-1-((1-phenylethyl)imino)-2,3-dihydro-1H-indene-4-carbonitrile with a yield of 87.8% and a purity of 95.0%.

According to the analysis of related databases, 60899-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Xu Guobin; Sun Guodong; Wang Zhongqing; Hu Yanqing; Su Wei; Luo Zhonghua; Huang Fangfang; (9 pag.)CN110615747; (2019); A;,
Nitrile – Wikipedia,
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Some common heterocyclic compound, 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, molecular formula is C8H6N2O2, 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. Application In Synthesis of 4-Methyl-3-nitrobenzonitrile

(b) 3-Amino-4-methylbenzonitrile 120 g of 3-Nitro-4-methylbenzonitrile were suspended in 1.2 l of EtOH and hydrogenated in the presence of 7 g of Pd/C (10%) with 50 l of hydrogen at room temperature. After removal of the catalyst, the solvent was stripped off. 95 g of pure product were obtained (97%). 1 H-NMR (DMSO-d6; delta in ppm): 7.1 (dd, 1H); 6.90 (d, 1H); 6.85 (dd, 1H); 5.35 (s, 2H, NH2 [sic]); 2.15 (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 939-79-7, its application will become more common.

Reference:
Patent; BASF Aktiengesellschaft; US5932567; (1999); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 57381-51-8, 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. 57381-51-8 name is 4-Chloro-2-fluorobenzonitrile, 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.

To a 3 L round bottom flask were added 4-chloro-2-fluorobenzonitrile (100 g, 0.64 mol) and methyl thioglycolate (70.0 ml, 0.77 mol) add 1.2 L of N, N-dimethylformamide and lower the internal temperature to -5 C. Sodium tert-butoxide (93.67 g, 0.96 mol) is slowly added, ensuring that the internal temperature does not exceed 0 C. After stirring at room temperature for 2 hours, Drop the reaction slowly into cold water. The resulting solid was stirred at room temperature, filtered, Drying afforded intermediate A-1. (142.9 g, 92%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Chloro-2-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Samsung SDI Co., Ltd; Samsung Electronics Co., Ltd.; Kim Byeong-gu; Kang Gi-uk; Kim Hyeong-seon; Ryu Dong-wan; Shin Chang-ju; Lee Han-il; Jang Gi-po; Jeong Seong-hyeon; (69 pag.)KR2019/32884; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts