Category: 20925-27-3

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. 20925-27-3, name is 4-Amino-2-chlorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H5ClN2

EXAMPLE 54A 2-chloro-4-iodobenzonitrile A solution of 4-amino-2-chlorobenzonitrile (30.5 g, 0.2 mol) in 1:1 diethyl ether/3M HCl (600 mL) at 0 C. was treated dropwise over 15 minutes with a solution of sodium nitrite (18 g, 0.26 mol) in water (100 mL), stirred 15 minutes, then treated with a solution of potassium iodide (50 g, 0.3 mol) in water (50 mL) dropwise over 45 minutes, warmed to room temperature, and stirred for 1.5 hours. The organic phase was washed with water (3*100 mL) and the combined aqueous layers were extracted with diethyl ether. The combined organic layers were combined, washed sequentially with saturated NaHCO3, 25% Na2S2O3, and brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 19:1/hexanes:ethyl acetate, triturated in hexanes, filtered, and dried to provide the desired product.

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; Claiborne, Akiyo K.; Gwaltney, II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2002/115640; (2002); A1;; ; Patent; Claiborne, Akiyo K.; Gwaltney II, Stephen L.; Hasvold, Lisa A.; Li, Qun; Li, Tongmei; Lin, Nan-Horng; Mantei, Robert A.; Rockway, Todd W.; Sham, Hing L.; Sullivan, Gerard M.; Tong, Yunsong; Wang, Gary; Wang, Le; Wang, Xilu; Wang, Wei-Bo; US2003/87940; (2003); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 20925-27-3, name is 4-Amino-2-chlorobenzonitrile, 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 20925-27-3, Application In Synthesis of 4-Amino-2-chlorobenzonitrile

Step 1: Synthesis of 2-chloro-4-isothiocyanatobenzonitrile (B) To a stirred solution of 4-amino-2-chlorobenzonitrile (A, 1 g, 6.55 mmol) in dichloromethane (9 mL) was added sodium bicarbonate (2.21 g, 26.31 mmol) and water (9 mL). The resulting mixture was cooled to 0 C., to which thiophosgene (817 mg, 7.11 mmol) was added in drop wise in 30 min at 0 C. The resulting mixture was then warmed up to room temperature and stirred at room temperature for 1 hour. The reaction mixture was diluted with dichloromethane (200 mL), washed with brine (50 mL*2), dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give a crude residue. The residue was purified by flash silica gel chromatography (eluent: ethyl acetate/petroleum ether (v:v=1:30)) to give desired product (yield: 71%)1HNMR (400 MHz, CDCl3): delta 7.69 (d, J=8.0 Hz, 1H), 7.38 (s, 1H), 7.28 (m, 1H);

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; Arvinas, Inc.; Crew, Andrew P.; Hornberger, Keith R.; Snyder, Lawrence B.; Zimmermann, Kurt; Wang, Jing; Berlin, Michael; Crews, Craig M.; Dong, Hanqing; (605 pag.)US2018/99940; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 20925-27-3, 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. 20925-27-3 name is 4-Amino-2-chlorobenzonitrile, 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: In a typical experiment, a solution of sodium hydrogen carbonate (62.72 mmol) in 20 mL of water was stirred for 10 min and to it was added dichloromethane (20 mL) followed by substituted aniline (15.68 mmol). The reaction mixture was cooled to 0 C, thiophosgene (23.52 mmol) was introduced dropwise over a period of 30 min and continuously stirred at room temperature for 1 h. The reaction mixture was washed with brine solution; the organic layer was dried over anhydrous sodium sulphate and concentrated to get a crude gummy compound which was recrystalized in hexane under cold condition. The precipitate was filtered and dried to get the desired compound. The products were characterized by analytical and spectral methods.

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

Reference:
Article; Khatik, Gopal L.; Kaur, Jasmine; Kumar, Varun; Tikoo, Kulbhushan; Venugopalan; Nair, Vipin A.; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3291 – 3301;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 20925-27-3, name is 4-Amino-2-chlorobenzonitrile, 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 20925-27-3, Safety of 4-Amino-2-chlorobenzonitrile

To a stirred solution of 4-amino-2-chlorobenzonitrile (5.02 g, 32.9 mmol) in dichloromethane (80 mL) was added N,N-diisopropylethylamine (17.0 mL, 97.8 mmol) and methanesulfonyl chloride (3.0 mL, 38.8 mmol) at-78 C. The reaction was then allowed to warm to room temperature slowly. After stirring at room temperature for 12 h, the reaction was quenched with 1 N hydrochloric acid. The organic phase was concentrated in vacuo and the residue was purified by flash chromatography (silica gel, 50:50 hexanes/ethyl acetate) to give the desired product.

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

Reference:
Patent; MERCK & CO., INC.; WO2005/108382; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts