Month: May 2021

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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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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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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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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Adding a certain compound to certain chemical reactions, such as: 21423-84-7, name is 2-Chloro-4-methylbenzonitrile, 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 21423-84-7, Recommanded Product: 21423-84-7

To a solution of 2-chloro-4-methylbenzonitrile (0.50 g, 3.31 mmol) in anhydrous THF (7 mL) at 0 C was added 1 M solution of phenyl magnesium bromide in THF (4.96 mL, 4.96 mmol) over 10 minutes and the resulting mixture was warmed to rt. The reaction mixture was stirred at rt for 30 minutes followed by heating to 60 C and stirred at the same temperature for 2 h. After completion of the i mine formation, the reaction mixture was cooled to 0 C and methanol (10 mL) was added very slowly followed by sodium borohydride (0.188 g, 4.96 mmol). The resulting mixture was warmed to rt and stirred overnight After completion of the reaction, solvent was removed under vacuum and water (20 mL) was added into the reaction mixture and extracted with ethyl acetate (2 x 35 mL). The combined organic layers were dried over Na2SO4 and concentrated. The product was purified by silica gel column chromatography (10% ethyl acetate/Hexanes) to provide title compound (0.16 g, 21 %), 1H NMR (400 MHz, DMSO-d6) delta ppm 7.59-7.61 (d, 1H), 7.24-7.32 (m, 4H), 7.15-7.19 (q, 3H), 5.37 (s, 1H), 2.31-2.34 (t, 1H), 2.26 (s, 3H).

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

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; WO2013/19621; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, 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 69395-13-7, Recommanded Product: 4-(2-Hydroxyethyl)benzonitrile

Compound 22:Ferrocene (11.0 mg, 0.050 mmol) was added sequentially to a 25 mL two-necked flask,4-cyanobenzene ethanol (43.2 mg, 0.25 mmol),Phenyl silane (109 [mu] L, 0.75 mmol)Tert-butyl hydroperoxide (88 [mu] L, 0.75 mmol)The gas was replaced with dry N2 for 3 times,Finally, dry tetrahydropyran (2.0 mL) was added under N2.The mixture was stirred at room temperature and heated to 80 C to carry out the reaction,Until the thin layer chromatography monitoring of raw materials is completed.At the end of the reaction, 15.0 mL of NaCl solution was added at room temperature,Extracted with ether 15.0mL three times, combined with organic phase decompression steaming,The product was purified by column chromatography in 65% yield.

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; Nanjing Normal University; Han Wei; Zhao Hongyuan; (19 pag.)CN107056732; (2017); A;,
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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. 5332-06-9, name is 4-Bromobutanenitrile, A new synthetic method of this compound is introduced below., SDS of cas: 5332-06-9

After 4-bromobutanenitrile (1.48 g, 10 mmol) was dissolved in acetonitrile (30 mL), sodium iodide (6 g, 40 mmol) was added thereto, and the mixture was stirred for 70 minutes at 60C. After the temperature was lowered to room temperature, water (30 mL) was added to the reaction material, and the result was extracted with ethyl acetate (30 mLx2). Excess iodine was removed by washing the organic layer with a 1% aqueous sodium thiosulfate solution, and the organic layer was washed with salted water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to give a target compound (1.86 g, 95%). 1H-NMR (300 MHz, CDCl3) delta 2.13 (m, 2H), 2.53 (t, J=13.8Hz, 2H), 3.30 (t, J=13Hz, 2H)

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; Korea Research Institute of Chemical Technology; SON, Jong Chan; KIM, Bong Jin; KIM, Jae Hak; LEE, Ill Young; YUN, Chang Soo; LEE, Sang Ho; LEE, Chong Kgo; (98 pag.)EP2781519; (2014); A1;,
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Some common heterocyclic compound, 621-03-4, name is 2-Cyano-N-phenylacetamide, molecular formula is C9H8N2O, 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. name: 2-Cyano-N-phenylacetamide

General procedure: 10 mmol of 2-cyano-N-phenylacetamides (4, 5), 10 mmol of aromatic aldehyde (6a-h) and malononitrile (7) were dissolved in 20 ml of methanol. The reaction mixture was heated on water bath for 8-16 h using piperidine as catalyst 24 (under TLC analysis). After completion of the reaction, the reaction mixture was cooled to room temperature; separated product was filtered, washed with methanol and crystallized from DMF to afford the desired products 8, 9. The compound 9d is reported in literature.25

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 621-03-4, its application will become more common.

Reference:
Article; Khatri, Taslimahemad T.; Shah, Viresh H.; Journal of the Korean Chemical Society; vol. 58; 4; (2014); p. 366 – 376;,
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17626-40-3, name is 3,4-Diaminobenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Recommanded Product: 17626-40-3

General procedure: Hydroximoyl chloride 10 (0.16g, 1mmol) was added slowly by small portions to a solution of the appropriate 1,2-diaminobenzene 3 (0.3g, 1.5mmol) in ethanol (5-10mL) at room temperature. The mixture was stirred at reflux for 0.5h followed by an additional hour at room temperature, diluted with water (10mL) and 0.1M aq HCl (5mL). The heterogeneous mixture was stirred for 1h. The precipitate was filtered, washed with water, and recrystallized from iPrOH/H2O.

The synthetic route of 17626-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stepanov, Andrei I.; Astrat’ev, Alexander A.; Sheremetev, Aleksei B.; Lagutina, Nataliya K.; Palysaeva, Nadezhda V.; Tyurin, Aleksei Yu.; Aleksandrova, Nataliya S.; Sadchikova, Nataliya P.; Suponitsky, Kyrill Yu.; Atamanenko, Olga P.; Konyushkin, Leonid D.; Semenov, Roman V.; Firgang, Sergei I.; Kiselyov, Alex S.; Semenova, Marina N.; Semenov, Victor V.; European Journal of Medicinal Chemistry; vol. 94; (2015); p. 237 – 251;,
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Electric Literature of 2941-29-9, A common heterocyclic compound, 2941-29-9, name is Cyclopentanone-2-carbonitrile, molecular formula is C6H7NO, 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.

100554] Step A: Preparation of 2-(2-(pyridin-2-yl)hydrazono)cyclopentane-carbonitrile:A solution of 2-hydrazinylpyridine (0.200 g, 1.83 mmol) and 2-oxocyclopentanecarbonitrile (0.200 g, 1.83 mmol) in MeOH (9.16 mL) was treated with concentrated HC1 (0.764 mL, 9.16 mmol) and refluxed for 16 hours. The reaction mixture was concentrated in vacuo, and then partitioned in water and DCM. After phase-separation, the aqueous layer was washed with DCM, basified (saturated NaHCO3, pH 10), and extracted with DCM. The combined organic layers were dried with MgSO4, filtered and concentrated. The crude material was purified by silica column chromatography, eluting with 100percent EtOAc to afford the product (0.289 g, 78.6percent yield). MS (apci) mlz 201.2 (M+H).

The synthetic route of 2941-29-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; ANDREWS, Steven Wade; BLAKE, James F.; BRANDHUBER, Barbara J.; KERCHER, Timothy; WINSKI, Shannon L.; WO2014/78325; (2014); A1;,
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