Category: nitriles-buliding-blocks

Electric Literature 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.

A mixture of 4-fluoro-3-trifluro-methylbenzonitrile (Fluorochem2223, 10 g, 52.8 mmol) and morpholine (9.25ml_, 105.7 mmol) was heated at 6O C under N2 for 8 hours. The mixture was cooled and diluted with water (100 ml_). The precipitate was filtered affording the title compound as a white solid (12.9 g, 95%). 1H NMR (CDCI3, 400 MHz) delta 7.92 (s, 1 H), 7.78- 7.81 (d, 1 H), 7.32-7.35 (d, 1 H), 3.84-3.87 (m, 4H), 3.04-3.06 (m, 4H). LC/MS (Method A): 257.1 (M+H)+. HPLC (Method B) Rt 3.61 min (Purity: 99.1%).

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; MERCK SERONO S.A.; WO2009/43889; (2009); A2;,
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Related Products of 10412-93-8,Some common heterocyclic compound, 10412-93-8, name is N-Benzyl-2-cyanoacetamide, molecular formula is C10H10N2O, 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 a solution of 5 (1.5 mmol) and 2a-s (3.1 mmol) in ethanol (10 mL) was added Et3N (0.1 mmol) dropwise at room temperature. The resulting mixture was stirred at 50 C for 2-3 h and then allowed to cool to room temperature. The product was precipitated from the reaction mixture, collected by filtration and washed with methanol (2-3 mL) to yield corresponding final products (6a-s).

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

Reference:
Article; Shaik, Jeelan Basha; Palaka, Bhagath Kumar; Penumala, Mohan; Kotapati, Kasi Viswanath; Devineni, Subba Rao; Eadlapalli, Siddhartha; Darla, M. Manidhar; Ampasala, Dinakara Rao; Vadde, Ramakrishna; Amooru, G. Damu; European Journal of Medicinal Chemistry; vol. 107; (2016); p. 219 – 232;,
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Application of 4640-67-9, 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. 4640-67-9 name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, 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: Under argon atmosphere, the corresponding beta-ketonitrile 2(1 mmol), water (3 mL), the ruthenium(II) complex 1 (0.028 g,0.05 mmol; 5 mol%) and NaO2CH (1.360 g, 20 mmol) were introducedinto a Teflon-capped sealed tube, and the reaction mixturestirred at 100 C for 24e48 h. The solvent was then removed undervacuum and the resulting solid residue purified by flash columnchromatography over silica gel using, unless otherwise stated, amixture of MeOH/EtOAc (1:10) as eluent. Characterization data forthe isolated beta-hydroxyamides are as follows: 3-(4-Fluorophenyl)-3-hydroxypropanamide (4a) [7g]: Lightbrown solid. Mp 108e110 C. Yield: 0.135 g (74%). 1H NMR(DMSO-d6, 300 MHz): d 7.37 (dd, 2H, J 8.7 and 5.7 Hz), 7.30 (br,1H), 7.14 (dd, 2H, J 8.7 and 8.7 Hz), 6.84 (br, 1H), 5.43 (d, 1H,J 4.5 Hz), 4.95 (m, 1H), 2.46e2.29 (m, 2H) ppm. 13C{1H} NMR(DMSO-d6, 100 MHz): d 172.6, 161.6 (d, J 241.9 Hz), 142.0, 128.1(d, 2C, J 7.9 Hz), 115.1 (d, 2C, J 21.2 Hz), 69.5, 45.8 ppm. 19F{1H}NMR (CD3OD, 282 MHz): d117.5 (s) ppm.

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

Reference:
Article; Gonzalez-Fernandez, Rebeca; Crochet, Pascale; Cadierno, Victorio; Journal of Organometallic Chemistry; vol. 896; (2019); p. 90 – 101;,
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Synthetic Route of 40497-11-8,Some common heterocyclic compound, 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, molecular formula is C7H8N2O2, 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.

0.01 mol of ethyl 2,3-dicyanopropionate was added to a three-necked flask. The prepared diazonium salt solution was dropped into the flask. The reaction was complete for 2 h. Adding aqueous ammonia, adjust the pH to 9-10. Reaction at room temperature for 2h. After completion of the reaction, the reaction mixture was extracted with 40 mL of dichloromethane. The organic layer was washed with water (2 x 30 mL), washed with saturated sodium chloride solution (1 x 40 mL), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 1.41 g of product, yield 66.8%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2,3-dicyanopropanoate, its application will become more common.

Reference:
Patent; Nanjing University of Technology; Wan, Rong; Wu, Shaohua; Guo, Chunwei; Guan, Xilin; Chen, Fuli; Han, Zhenyu; Fu, Xiaohuan; (14 pag.)CN105601632; (2016); A;,
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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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H6N2O2

NaH (4.34 g, 90.4 mmol) was stirred in a solvent of tetrahydrofuran (20 mL) at 0 C. The reaction solution was slowly added with 2-(3-nitrophenyl)acetonitrile (2.2 g, 13.6 mmol), and stirred for about 30 minutes at 0 C. The reaction solution was added with MeI (6.67 mL, 107 mmol), followed by stirring for about 12 hours at room temperature. The reaction mixture was added with an ice water. The organic layer was separated out and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography (EA:HEX=1:9) to obtain the title compound (0.6 g, 23%). 1H-NMR Spectrum (300 MHz, DMSO-d6): delta 8.33 (s, 1H), 8.22 (d, 1H), 7.91 (d, 1H), 7.65 (t, 1H), 1.81 (s, 6H). MS (ESI+, m/z): 191 [M+H]+

According to the analysis of related databases, 621-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HANMI PHARM. CO., LTD.; Bae, In Hwan; Han, Sang Mi; Kwak, Eun Joo; Ahn, Young Gil; Suh, Kwee Hyun; US2015/191450; (2015); A1;,
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Reference of 123-06-8,Some common heterocyclic compound, 123-06-8, name is Ethoxymethylenemalononitrile, molecular formula is C6H6N2O, 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 t-butylhydrazine hydrochloride (4.67 g, 53 mmol) and triethylamine (5.35 g, 53 mmol) in anhydrous ethanol (250 ml) was stirred and ethoxymethylene malononitrile (6.47 g, 53 mmol) was slowly added in portions. The mixture was heated at reflux for 3 hr. The solvent was removed in vacuo and the product was crystallized from ethyl acetate -hexane followed by ether to afford the title compound as light pale brown crystals (5.6 g, 64.4 %); LC/MS, API-ES, Neg, (M-H)”, 163.0.

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

Reference:
Patent; FOLDRX PHARMACEUTICALS, INC.; WHITEHEAD INSTITUTE FOR BIOMEDICAL RESEARCH; WO2007/126841; (2007); A2;,
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Electric Literature of 36282-26-5, A common heterocyclic compound, 36282-26-5, name is 2-Bromo-4-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

To a stirred solution of 2-bromo-4-fluorobenzonitrile (5 g, 25 mmol) and Ti(Oi-Pr)4 (9.05 mL, 27.5 mmol) in ether (100 mL) at -78 C was added EtMgBr (18.3 mL,55 mmol) drop wise. The solution was allowed to warm to room temperature and stirred for 1 hour before BF3-Et20 (6.25 mL) was added and stirring continued at room temperature for another 1 hour. The reaction solution was quenched with 1 N HC1 solution, and washed with EtOAc. The aqueous layer was adjusted to pH~10 with aq. NaOH (2 N) solution and then exacted with EtOAc (3 x). The combined organic layers were dried over anhy.Na2S04, filtered, and concentrated in vacuo. The residue was then purified by column chromatography to give title compound (3.0 g, yield 52.2%) as yellowish oil.

The synthetic route of 36282-26-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
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Application of 17417-09-3, 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. 17417-09-3 name is 2-Fluoro-5-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.

9.1. 2-(Dimethylamino)-5-nitrobenzonitrile: 1.66 g (10.0 mmol) of 2-fluoro-5-nitrobenzonitrile, 1.22 g (15.1 mmol) of dimethylamine hydrochloride and 3.46 g (25.1 mmol) of potassium bicarbonate is dissolved, under an argon atmosphere, in DMF (30 ml) then the reaction medium is heated at a temperature of 80 C. for 18 hours. The reaction mixture is cooled down to 0 C. and ice-cooled water is added. The reaction mixture is extracted with ethyl acetate and the organic phase is washed successively with 50 ml of water and 50 ml of salt water, dried over magnesium sulphate, filtered and concentrated under vacuum. The evaporation residue is purified by trituration with isopropyl ether and the solid obtained is filtered and rinsed with isopentane in order to obtain after drying 2.0 g of a solid yellow product (yield 100%). Melting point: 109-110.5 C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Fluoro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Societe de Conseils de Recherches et d’Applications Scientifiques (S.C.R.A.S.); US6605637; (2003); B1;,
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Application of 96606-37-0, The chemical industry reduces the impact on the environment during synthesis 96606-37-0, name is 2,4,6-Trifluorobenzonitrile, I believe this compound will play a more active role in future production and life.

2,4,6-trifluorobenzonitrile (0.25g, 1.6mmol), potassium carbonate (0.99g, 7.2mmol), 2-phenylbenzimidazole (1.02g, 5.2mmol), DMSO 8ml , 150 heated to reflux 12h.Cooling to room temperature the precipitated solid was poured into 200ml of water was stirred 0.5h, filtered off with suction to give a white solid, purified by column chromatography to give a white solid 0.95g, 88% yield

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, 2,4,6-Trifluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Nanjing University of Technology; TAO, YOU TIAN; WANG, FANG FANG; TANG, CHAO; HUANG, WEI; (6 pag.)CN104610162; (2016); B;,
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Reference of 160892-07-9, The chemical industry reduces the impact on the environment during synthesis 160892-07-9, name is 5-Bromoisophthalonitrile, I believe this compound will play a more active role in future production and life.

In a nitrogen atmosphere5-Bromoisophthalonitrile (30.0 g, 144.9 mmol)And (3,5-dichlorophenyl) boronic acid (30.4 g, 159.4 mmol)Were added to 400 ml of tetrahydrofuran, and the mixture was stirred and refluxed.After this, potassium carbonate (60.1 g, 434.7 mmol)In 180 ml of waterAfter thoroughly stirring, tetrakistriphenyl-phosphinopalladium (5.0 g, 4.4 mmol) was added thereto. After 8 hours of reaction, the temperature was lowered to room temperature and filtered.The filtrate was extracted with chloroform and water, and then the organic layer was dried with magnesium sulfate.The organic layer was then distilled under reduced pressure and recrystallized using ethyl acetate.The resulting solid was filtered and dried to give Compound 5A (30.5 g, 77%).

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, 5-Bromoisophthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LG CHEM, LTD.; JUNG, Min Woo; LEE, Dong Hoon; HUH, Jung oh; JANG, Boon jae; KANG, Min young; HEO, Dong Uk; HAN, Mi yeon; (26 pag.)KR2017/92131; (2017); A;,
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