Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 41429-22-5, name is 2-(2-(Difluoromethoxy)phenyl)acetonitrile, 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 41429-22-5, Formula: C9H7F2NO

Synthesis of ethyl (2-difluoromethoxyphenyl)acetate (2-Difluoromethoxyphenyl)acetonitrile (1.45 g) was added dropwise to a solution of chlorotrimethylsilane (2.23 mL) in ethanol (2.0 mL), and the reaction solution was stirred at 50C for five hours. The reaction solution was left to cool to room temperature. Then, potassium carbonate, water and ethyl acetate were added and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 620 mg of the title compound. The property values of the compound are as follows. 1H-NMR (CDCl3) delta (ppm): 1.26 (t, J=7.2Hz, 3H), 3.68 (s, 2H), 4.16 (q, 7.2Hz, 2H), 6.48 (t, J=74.4Hz, 1H), 7.13-7.32 (m, 4H).

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-(2-(Difluoromethoxy)phenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Eisai R&D Management Co., Ltd.; EP2181992; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 2947-60-6, 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. 2947-60-6 name is 3-Methylbenzyl cyanide, 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.

Example 1 Synthesis of 1-methoxy-2-(3-methylphenyl)ethanimine (Compound 1) Cold 4 M hydrogen chloride in dioxane (184 ml, 0.763 mol) is added to a stirred and cooled (0 C.) mixture of 3-methylbenzyl cyanide (25 g, 0.19 mol) in anhydrous methanol (23 ml, 0.57 mol) and anhydrous ether (100 ml). The resulting reaction mixture is stirred at 0 C. for an additional hour and then it is placed in a refrigerator (0-5 C.) for 48 hours (during this time a small amount of white crystalline material precipitated). The reaction mixture is removed from the refrigerator and warmed to approximately 40 C. using a warm water bath. Nitrogen gas is then bubbled through the warm reaction mixture to remove excess hydrogen chloride. The volume of the solvent is reduced in vacuo, and anhydrous ether is added to effect precipitation. The precipitate is collected by filtration, washed with ether and dried under vacuum to afford 31 g (82%) of the crystalline imidate hydrochloride salt (1) as a white solid. 1H NMR (CDCl3): delta 12.82 (br s, 1H), 11.85(br s, 1H), 7.0-7.25(m, 5H), 4.25 (s, 3H), 4.0(s, 2H), 2.31 (s, 3H). 13C NMR (CDCl3): delta 178.7, 139.3, 131.2, 130.5, 129.5, 129.3, 126.9, 61.3, 39.3, 21.6.

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

Reference:
Patent; Kolb, Hartmuth C.; Kanamarlapudi, Ramanaiah C.; Richardson, Paul F.; Khan, Gaznabi; US2003/153728; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 191014-55-8, A common heterocyclic compound, 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, molecular formula is C8H6FNO, 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 solution of 1 g of 4-fluoro-2-methoxy-benzonitrile in 15 mL of dichloroethane was added 1.1 g of aluminum trichloride. The resulting mixture was refluxed for 1 day then poured slowly into water and extracted with ethyl acetate. The organic extracts were washed twice with 10% aqueous solution of sodium hydroxide. The combined basic layers were washed twice with ethyl acetate, acidified with concentrated aqueous solution of hydrochloric acid and extracted three times with ethyl acetate. The combined organic extracts were washed with water, with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to give 0.78 g of 4-fluoro-2-hydroxy-benzonitrile as a white solid.C7H4FNO (137.11), MS (ESI): 138.17 (M+H+).

The synthetic route of 191014-55-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANOFI-AVENTIS; US2008/261979; (2008); 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. 13726-21-1, name is 2-(4-Chloro-3-methoxyphenyl)acetonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(4-Chloro-3-methoxyphenyl)acetonitrile

(4-Chloro-3-hydroxy-phenyl)acetonitrile BBr3 (17 g, 66 mmol) was slowly added to a solution of 2-(4-chloro-3-methoxyphenyl)acetonitrile (12 g, 66 mmol) in dichloromethane (120 mL) at -78 C. under N2. The reaction temperature was slowly increased to room temperature. The reaction mixture was stirred overnight and then poured into ice and water. The organic layer was separated, and the aqueous layer was extracted with dichloromethane (40 mL*3). The combined organic layers were washed with water, brine, dried over Na2SO4, and concentrated under vacuum to give (4-chloro-3-hydroxy-phenyl)-acetonitrile (9.3 g, 85%). 1H NMR (300 MHz, CDCl3) delta 7.34 (d, J=8.4 Hz, 1H), 7.02 (d, J=2.1 Hz, 1H), 6.87 (dd, J=2.1, 8.4 Hz, 1H), 5.15 (brs, 1H), 3.72 (s, 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; Vertex Pharmaceuticals Incorported; US2011/98311; (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. 508203-48-3, name is 2,3-Difluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 508203-48-3

To a suspension of 2,3-difluoro-4-methylbenzonitrile (5.0 g, 32.6 mmcl) in ethanol (111 mL) at25C was added hydroxylamine hydrochloride (4.5 g, 65.3 mmol). The reaction mixture was heated at80C for 2 hours. After cooling to room temperature, the volatiles were removed under reduced pressurethus affording a white solid that was used in the next transformation without purification.1H NMR (400 MHz, CDCI3) oe ppm: 7.30 (m, 1H), 6.95 (m, 1H), 6.50 (brs, 1H), 5.05 (brs, 2H),2.30 (s, 3H).

According to the analysis of related databases, 508203-48-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; BEAUDEGNIES, Renaud; POULIOT, Martin; HAAS, Ulrich, Johannes; (161 pag.)WO2018/177894; (2018); 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. 4387-32-0, name is 2-Chloro-5-methylbenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Chloro-5-methylbenzonitrile

To a solution of 2-chloro-5-methyl-benzonitrile (9.0 g, 59.4 mmol) in anhydrous THF (90 mL) at 0 C was added BH3-THF (1.0 M, 178 mL, 178 mmol) dropwise under a nitrogenatmosphere. The mixture was stirred at room temperature for 12 h. The reaction was quenched with 2N HC1 (110 mL) at 0 C and then heated to 70 C for 1 h. After cooling the reaction to room temperature, the solution was washed with DCM (150 mL). The aqueous phase was basified with iN NaOH to pH 8 and then extracted with DCM (150 mL x 3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give thetitle compound (5.8 g, 63%) as yellow oil. ?HNMR (400 IVIFIz, CDC13) 7.22 (d, J 8.0 Hz,1H), 7.17 (s, 1H), 6.99 (d, J= 8.0 Hz, 1H), 3.88 (s, 2H), 2.32 (s, 3H).

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; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 34662-24-3, A common heterocyclic compound, 34662-24-3, name is 2-Chloro-3-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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.

Step c) intermediate 11Synthesis of 2-[(2-hydroxyethyl)amino]-3-nitrobenzonitrile2-chloro-3-nitrobenzonitrile (74g, 0.408 mol) is mixed with ethanol (370 ml) and ethanolamine (57 ml). The mixture is stirred for 16 hrs at room temperature. To complete the reaction, the mixture is refluxed for 2 hours. After cooling, the mixture is concentrated under vacuum; the product precipitates as a red solid. To eliminate the ethanolamine hydrochloride salt, the suspension is triturated with 500 ml of water and filtrated under vacuum. The solid is washed with ethanol and ether then dried to give the desired product (75g, 89%).IH NMR (300MHz, DMSO-d6) delta ppm 3.55-3.60 (m,2H) 3.69-3.74 (m,2H) 6.75 (dd, 7=7.63, 8.52 Hz, 2H) 7.90 (dd, /=7.63, 1.76 Hz, 2H) 8.27 (dd, /=8.52, 1.76 Hz, IH) 3.35 m, IH)

The synthetic route of 34662-24-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2008/18827; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 175596-01-7 as follows. Recommanded Product: 175596-01-7

Preparation 91 4-Aminomethyl-2-fluoro-benzoic acid methyl ester Add a slurry of Raney nickel in ethanol (1.2 g, 1.2 ml) to 4-cyano-2-fluoro-benzoic acid methyl ester (5.8 g, 30.0 mmol) in 2N ammonia in methanol (580 mL). Purge with nitrogen gas (3*), purge with hydrogen gas (3*), and pressurize with hydrogen gas to 419 KPa. Heat the reaction at 40 C. for 18 hrs. Allow to cool to room temperature and filter the reaction mixture. Concentrate the filtrate to the crude title compound (6.9 g, 99%). MS (m/z): 184 (M+1).

According to the analysis of related databases, 175596-01-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Khilevich, Albert; Liu, Bin; Mayhugh, Daniel Ray; Schkeryantz, Jeffrey Michael; Zhang, Deyi; US2010/16373; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 86770-80-1, name is 3,3-Difluorocyclobutanecarbonitrile, 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 86770-80-1, category: nitriles-buliding-blocks

EXAMPLE 20 Preparation of 1-(3-chloropyridin-2-yl)-3,3-difluorocyclobutanecarbonitrile To a 100 mL round bottom flask was added 2,3-dichloropyridine (2.9 g, 20 mmol), 3,3-difluorocyclobutanecarbonitrile (2.1 g, 18 mmol), and toluene (50 mL). The mixture was cooled to C. and sodium hexamethyldisilazide (NaHMDS, 2.0 M in THF, 11 mL, 22 mmol) was added. The reaction mixture was warmed to rt and stirred for 2 h. The mixture was then diluted with EtOAc (20 mL) and water (20 mL). The aqueous layer was extracted with EtOAc and the combined organic phases were washed with brine, dried over Na2SO4, and concentrated to provide the desired product (3.4 g) as a colorless oil.

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; Cytokinetics, Inc.; Ashcraft, Luke W.; Bergnes, Gustave; Collibee, Scott; Chuang, Chihyuan; Gardina, Jeff; Morgan, Bradley P.; Muci, Alex R.; Qian, Xiangping; Romero, Antonio; Warrington, Jeffrey; Yang, Zhe; US9133123; (2015); B2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 13726-21-1, These common heterocyclic compound, 13726-21-1, name is 2-(4-Chloro-3-methoxyphenyl)acetonitrile, 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.

The third process; (4-Chloro-3-methoxyphenyl) acetic acid methyl ester; Potassium hydroxide (5.86 g) was dissolved in water (25 ml) and the mixture was added to a solution of 4-chloro-3-methoxyphenylacetonitrile (3.80 g) in ethanol (80 ml) at room temperature. The reaction solution was refluxed for 1.5 hours. After cooling, concentrated hydrochloric acid (8.8 ml) and water (50 ml) were added to the reaction solution and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (100 ml) and concentrated sulphuric acid was added thereto. The mixture was refluxed for 1.45 hours. After cooling, the reaction solvent was evaporated under reduced pressure and water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was washed with brine, and dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give a title compound (4.43 g). The yield was 99 %. 1H-NMR (CDCl3) delta: 3.61(2H,s), 3.71(3H,s), 3.91(3H,s), 6.81(1H,dd,J=1.8,8.1Hz), 6.87(1H,d,J=1.8Hz), 7.30(1H,d,J=8.1Hz).

The synthetic route of 13726-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi Co., Ltd.; EP1887000; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts