Tag: M.W=100-200

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. 6283-71-2, name is Dimethyl 2-cyanosuccinate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Dimethyl 2-cyanosuccinate

Preparation 100; 1- [2, 6-dichloro-4-pentafluorothiophenyl]-5-hydroxy-1 H-pyrazole-3-carbonitrile; Sodium nitrite (1.32 g, 19.1 mmol) was added carefully to sulphuric acid (concentrated, 6.8 ml), whilst cooling the solution to 0°C. The solution was heated to 60°C for 30 min, allowed to cool and then diluted with acetic acid (12 ml). To the solution was added 2, 6-dichloro-4-pentafluorothiophenylamine (WO 9421606 A1, 5.0 mg, 17.4 mmol) in acetic acid (11 ml) and the reaction mixture was heated at 55°C for 1 h. To a solution of dimethyl 2-cyanosuccinate (Hall, H. K. , Jr.; Ykman, P. , J. Am. Chem. Soc. (1975), 97 (4), 800-807,3. 09 g, 18.1 mmol) in acetic acid (24 mi) and water (36 ml) was added dropwise the solution of the diazonium salt, followed by sodium acetate (24.2 g) in water (42 ml). The reaction mixture was then stirred at room temperature for 30 min. The reaction mixture was poured into ice/water (200 ml) and the mixture was extracted with dichloromethane (4 x 60 ml). The combined extracts were then washed with ammonium hydroxide (48 ml), dried and concentrated in vacuo. To a solution of sodium methoxide (25 wt. percent, 11.5 ml, 50.1 mmol) in methanol (450 ml) was added dropwise a solution of the residue in methanol (100 ml). The reaction mixture was then stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and to the residue was added water. This solution was adjusted to pH 1 by addition of hydrochloric acid (4N) and the mixture was extracted with dichloromethane (3 x 100 ml). The combined extracts were dried (MgS04) and concentrated in vacuo. The residue was purified by column chromatography, eluting with hexane/ethyl acetate [3: 1]. The appropriate fractions were combined and concentrated to give the titled compound (4. 5g). Experimental MH+ 379.8 ; expected 380.0

The synthetic route of 6283-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/90313; (2005); A1;,
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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 64113-85-5 as follows. category: nitriles-buliding-blocks

General procedure: The heterocyclic derivative (0.99 mmol) and 5 mL THF is cooled to -78 oC, n-BuLi solution ( 0.5, mL, 1.2 eq) is added, the mixture is stirred 1 hr, after which 2-cyano-4-methyhlbiphenyl (192 mg, 0.99 mmol, dissolved in 5 mL THF) is added dropwise, The solution is then stirred 1 hr at -78 oC, then allowed to warm to room temperature and stirred for 6 hr. After this, 10 mL of 6M HCl is added and the mixture is stirred overnight. The solution is then basified with 10M NaOH and the products are partitioned between ether and water. The aqueous layer is further extracted (2x with ether) and the combined extracts are washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent is then removed under reduced pressure and the crude mixture is purified by column chromatography (1:1, hexanes: ethyl acetate).

According to the analysis of related databases, 64113-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Stentzel, Michael R.; Klumpp, Douglas A.; Tetrahedron Letters; vol. 60; 25; (2019); p. 1675 – 1677;,
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Application of 5312-97-0, A common heterocyclic compound, 5312-97-0, name is 2,5-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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.

Intermediate 42a) To solution of 2,5-dimethoxybenzonitrile (1.5 g) in dry Et20 (7 mL) was added propyl magnesium chloride (2 M in Et20, 9.2 mL) and the resulting mixture was heated to 40 C for 2 h. The mixture was chilled and 4 M HCI (9 mL) was carefully added and it was stirred at ambient temperature for 16 h. The mixture was extracted with EtOAc, the combined organic layers were washed with water, were dried and the volatiles were removed under reduced pressure. The residue was purified by column chromatography (Interchim cartridge 15SiHP / 120 g, Cy / EtOAc) to yield the desired compound (57% yield). LC-MS {Method 1): m/z [M+Hf = 209.3 (MW calc. = 208.25); R, = 3.5 min.

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; GRUeNENTHAL GMBH; NORDHOFF, Sonja; WACHTEN, Sebastian; KLESS, Achim; VOSS, Felix; RITTER, Stefanie; WO2014/108336; (2014); A1;,
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Application of 262298-02-2,Some common heterocyclic compound, 262298-02-2, name is 4-Methoxy-2-methylphenylacetonitrile, molecular formula is C10H11NO, 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.

Reference example 2 1-cyano-1-(2-methyl-4-methoxyphenyl)propan-2-one Under argon atmosphere, to a solution of the compound prepared in reference example 1 (11.7 g) in ethyl acetate (60 ml), metallic sodium (2.3 g) was added in numbers. The mixture was stirred for 2 hours at 50 §C. Ethyl acetate (40 ml) was added to the reaction mixture, and the mixture was refluxed for 2.5 hours and then it was stirred overnight at room temperature. A precipitation matter was collected by filtration, and it was washed with diethyl ether. The obtained crystal was dissolved into water (300 ml). The solution was adjusted pH 4 by adding 2N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated to give the title compound (12.06 g) having the following physical data. TLC: Rf 0.45 (n-hexane: ethyl acetate = 1: 1).

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

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1354884; (2003); A1;,
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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. 10365-94-3, name is 1,3,5-Benzenetricarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3,5-Benzenetricarbonitrile

(3) 100 g of 1,3,5-benzotrinitrile and 3 g of Raney-Ni, 400 mL of ethanol are added to a 1 L hydrogenation reactor, and H2 is continuously charged, so that the pressure of the system is always maintained at 8 MPa during the reaction. After the reaction was performed at a reaction temperature of 110 C. for 1.5 h, the temperature was lowered. When the temperature in the reaction vessel was lowered to room temperature, the gas was purged, and 1,3,5-benzenetrimethylamine (having a purity of 99% or more) was obtained by filtration and recrystallization. The yield was 88% by weight.

According to the analysis of related databases, 10365-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sinopec Yangzi Petrochemical Co., Ltd.; Sinopec Corporation; Sun Hailong; Li Na; Gao Yilong; Wei Yanyu; Chen Xinhua; Miao Jun; Kan Lin; Bai Jiye; Chen Shaohui; Yang Aiwu; Xu Yuexing; (30 pag.)CN105001032; (2018); B;,
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Related Products of 354814-19-0, 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. 354814-19-0 name is 5-Amino-2-(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.

Method 6; To a solution of 5-amino-2-trifluoromethylbenzonitrile (380 mg, 2.04 mmol) in pyridine (5 mL) was added 2-trifluoromethylbenzenesulfonyl chloride (500 mg, 2.04 mmol) and DMAP (25 mg, 0.204 mmol). The reaction mixture was stirred at room temperature for 48 hours. The reaction was quenched by the addition of 2M HCI (aq) (50 mL) and the mixture extracted into EtOAc (50 mL). The organic layer was collected, washed with 2M HCI (aq) (50 mL) and concentrated in vacuo. The residue was purified using reverse phase chromatography eluting with 10-60% (0.1 % ammonium hydroxide in MeCN) in water to afford the title compound as a colourless solid (318 mg, 40%). 1H NMR (400M Hz, CDCI3): delta ppm 7.19 (d, 1 H), 7.40 (d, 1 H), 7.56 (d, 1 H), 7.62 (d, 1 H), 7.64-7.78 (m, 2H), 7.91 (dd, 1 H), 8.20 (dd, 1 H). MS m/z 393 [M-H]-

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

Reference:
Patent; PFIZER LIMITED; OWEN, Robert McKenzie; STORER, Robert Ian; (82 pag.)WO2016/34971; (2016); A1;,
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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. 39263-32-6, name is 2-Amino-5-bromobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 39263-32-6

Using a literature procedure described in the following literature reference which is herein incorporated by reference in its entirety for all purposes as if fully set forth herein, a dry round bottom flask was charged with 2-amino-5-bromo benzonitrile (1 equivalent) and zinc cyanide (2 equivalents), and DMF was added: J. Med. Chem. 2000,43, 4063. Nitrogen was bubbled through the solution for 5 minutes, and Pd [P (Ph) 3] 4 was added in one portion. The reaction mixture was stirred at 90 C overnight. After cooling to room temperature, saturated NAHC03 was added, and the mixture was extracted with EtOAc. The organic extracts were collected and dried (NA2SO4). Evaporation of the solvent under reduced pressure and purification by column chromatography on silicagel (2% methanol in methylene chloride) afforded the desired 4-aminobenzene-1, 3-DICARBONITRILE as a white solid. GC/MS M/Z : 143 (M+, 100%), Rt 14.7 minutes

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; CHIRON CORPORATION; WO2004/18419; (2004); A2;,
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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. 34662-30-1, name is 3-Chloro-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloro-5-nitrobenzonitrile

3-Chloro-5-nitrobenzonitrile (30.0 g) was dissolved in a mixture of water (85 mL) and H2SO4 (250 mL) and heated under an N2 atmosphere at 150 C. for 2 h. The mixture was cooled to ambient temperature and poured onto ice (1 L). The resulting solid was collected by vacuum filtration, and the filtrate was extracted with ethyl acetate. The extract and solid were combined, washed with water and brine, then were dried over MgSO4, filtered, and evaporated. The residue was dissolved in 1:1 water/MeOH (200 mL) with heating, treated with decolorizing charcoal and filtered. Water (100 mL) was added and the mixture was allowed to cool and crystallize. The product was obtained as pale yellow crystals. 1H-NMR (d6-DMSO): delta 14.00 (1H, br s), 8.51 (2H, m), 8.29 (1H, m). 13C-NMR (d6-DMSO): delta 164.9, 149.2, 135.2, 135.0, 134.5, 127.7, 122.9.

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; Ashley, Gary W.; Menzella, Hugo; Wee, Janice Lau; Carney, John R.; US2008/188450; (2008); A1;,
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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. 34662-24-3, name is 2-Chloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Chloro-3-nitrobenzonitrile

To a solution of 2-chloro-3-nitrobenzonitrile (200 mg, 1 .3 mmol) in absolute THF (20 mL) was added dropwise BH3SMe2 (0.2 mL, 2.6 mmol) under nitrogen atmosphere protection. The mixture was stirred at reflux for 2 hrs. Then 2 N HCI (1 .5 mL) was added to the mixture and the mixture was stirred at reflux for 1 hour. The mixture was condensed to crude compound CI-1 -5B (248 mg) as yellow solid.

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 34662-24-3.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HENDRICKSON, Thomas, Francis; HO, Koc-Kan; SAUNDERS, Michael, David; STEVENS, Brian, John; SWIERCZEK, Krzysztof; WRIGHT, Kevin, Bret; WO2013/62945; (2013); A1;,
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Application of 64113-85-5, 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 64113-85-5 as follows.

2-cyanobiphenyl-4-carboxylic acid, 11 The compound 9 (1.1 g, 6.0 mmol) is dissolved in pyridine (10 mL) and water (2 mL). To this solid, KMnO4 (0.9 g, 6.0 mmol, 1 equiv.) is added, and the reaction is heated to reflux. Additional 0.25 equiv. of KMnO4 is added every 30 min. for 1O h. The reaction is further refluxed for 50 h and filtered hot and the filtrate is evaporated under reduced pressure. The residue is dissolved in 20 mL water with heating. The solution is acidified to pH 2 with cone. HCl after cooling to room temperature. The white precipitate is collected by filtration and washed generously with cold water and the product is dried under vacuum overnight. Yield 1.1 g, 86 %; mp 195-200 0C; 1HNMR (400 MHz, CDCl3) delta 2; 13CNMR (101 MHz, CDCl3) delta 2; IR (Neat, cm’1); GC-MS (EI) m/z (M+); Anal. (Ci4Hi ^0.0.75H2O) C, H, N.

According to the analysis of related databases, 64113-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GOVERNMENT OF THE UNITED STATES OF AMERICA, REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; WO2008/92072; (2008); A2;,
Nitrile – Wikipedia,
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