Tag: M.W=100-200

Electric Literature of 115279-73-7, The chemical industry reduces the impact on the environment during synthesis 115279-73-7, name is 1-(4-Aminophenyl)cyclopentanecarbonitrile, I believe this compound will play a more active role in future production and life.

In a 500 ml four-necked flask equipped with a stirrer, thermometer and distillation system, add 100 g of N,N-dimethylformamide, 11.2 g (0.06 mol) of 1-(4-aminophenyl)cyclopentylcarbonitrile (V), 0.2 g of cuprous chloride. While maintaining the internal temperature between 95 and 100 C, 12.2 g (0.05 mol) of methyl 2-[(pyridin-4-ylmethyl)amino]-3-pyridinecarboxylate (IV1) prepared in Example 3 and 30 g N,N-dimethylformamide were added dropwise. The solution of N,N-dimethylformamide is added dropwise in about 1 hour, after which the reaction is stirred at 100-105 C for 4 hours, and the formed methanol is distilled off, the reaction is completed, the temperature is lowered to 20-25 C, and the filter cake is used for filtration. After washing with 20 g of N,N-dimethylformamide, the filtrate was combined, and N,N-dimethylformamide was evaporated under reduced pressure. The residue was crystallized from methyl t-butyl ether, filtered and dried. 18.3 g of a white solid powder of agingatin (I) was obtained in a yield of 92.2%, a liquid phase purity of 99.96% and a melting point of 158.5-160.0 C.

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, 1-(4-Aminophenyl)cyclopentanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Cui Qingrong; Liu Yuesheng; Qu Hu; Lv Qiangsan; Ju Lizhu; (10 pag.)CN109020881; (2018); 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. 2032-34-0, name is 3,3-Diethoxypropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2032-34-0

General procedure: Method I. A mixture of Py (4.4 ml) and AcOH (3.0 ml) was stirred and treated by the addition of 5-aminoazole1a-h (0.01 mol) and (2E)-(3-morpholin-4-yl)-acrylonitrile (2) (1.38 g, 0.01 mol). The obtained mixture was refluxed at 150C for 5 h. After refluxing, the mixture was cooled. The precipitate that formed was filtered off, washed with a small amount of EtOH, and dried. Method II. A solution (or suspension) of the appropriate aminoazole 1a-h (0.01 mol) in solvent (15 ml) (EtOH in the case of compound 3a, dioxane in the case of compounds 3b-h) was stirred at 50C and treated by adding 3,3-diethoxypropionitrile (4) (1.5 ml, 0.01 mol), then 36% HCl solution (0.86 ml, 0.01 mol). The reaction mixture was refluxed for 2.5-3 h, the suspension (or solution) was cooled to room temperature, and the target product was isolated by the method indicated for each particular compound.

According to the analysis of related databases, 2032-34-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gazizov, Denis A.; Fedotov, Victor V.; Gorbunov, Evgeny B.; Ulomskiy, Evgeny N.; Yeltsov, Oleg S.; Rusinov, Gennady L.; Rusinov, Vladimir L.; Chemistry of Heterocyclic Compounds; vol. 55; 6; (2019); p. 573 – 577; Khim. Geterotsikl. Soedin.; vol. 55; 6; (2019); p. 573 – 577,5;,
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Application of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, 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: AlCl3 (15 molpercent) was added to a solution of DAMN (1 mmol), ketone (1 mmol) and isocyanide (1 mmol), in 5 ml of CH3CN. The resulting mixture was stirred for an appropriate time at room temperature. After completion of the reaction, as indicated by thin-layer chromatography (TLC; ethyl acetate=n-hexane 3=1), the product was precipitated by addition of 10 ml of water. The precipitate was filtered off, washed with water, and then recrystallized from acetone. In the case of aromatic aldehyde, precipitate after filtration was loaded on column chromatography with 20percent ethyl acetate?hexane as an eluent system to furnish the product.

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

Reference:
Article; Bhosale, Shrikar M.; Naik, Nilesh H.; Kusurkar, Radhika S.; Synthetic Communications; vol. 43; 23; (2013); p. 3163 – 3169;,
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26830-95-5, name is 4-Methyl-2-nitrobenzonitrile, 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. Safety of 4-Methyl-2-nitrobenzonitrile

Example 17: Alternative preparation of 4-cyano-3-nitro-benzoic acid; Under an inert atmosphere, periodic acid (492 g, 2.17 mol) was dissolved in acetonitrile (7.7 1) with vigorous stirring, and then, after 15 minutes chromium(VI) oxide (25 g, 0.25 mol) and 4-methyl-2-nitro-benzonitrile (100 g, 0.62 mol) were added successively. The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was decanted and the supernatant filtered. The filtrate was concentrated and the residue partitioned between aqueous sodium carbonate (IM) and dichloromethane. The precipitate was isolated by filtration to give 4-cyano-3-nitro-benzoic acid (150 g). The filtrate was extracted twice with dichloromethane and was then acidified by addition of aqueous hydrochloric acid (4N) to pH 1. The acidified filtrate was then extracted three times with dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated. This residue was partitioned between aqueous sodium carbonate (IM) and dichloromethane. The precipitate was isolated by filtration to give 4-cyano-3-nitro-benzoic acid (26.67 g). Total yield: 150 g + 26.67 g = 176.67 g; 74.5 % yield.

The synthetic route of 26830-95-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; WO2008/74427; (2008); 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. 4623-24-9, name is 2-(3-Aminophenyl)acetonitrile, A new synthetic method of this compound is introduced below., name: 2-(3-Aminophenyl)acetonitrile

To a cold (0 C) solution of Intermediate BD (500mg, 3.78 mmol) and triethylamine (0.63 mL, 4.48 mmol) in dichloromethane (10 mL) was added slowly methanesulfonyl chloride (0.35 mL, 4.49 mmol) over 5 minutes. After the addition was complete, the reaction mixture was allowed to reach room temperature and stirred for 2 hours. The reaction mixture was diluted with dichloromethane (10 mL), washed with water (2 chi 20 mL) and brine (10 mL), dried over anhydrous Na2S04, and the solvent was removed to afford the crude product. This material was purified by column chromatography (silica gel 100-200 mesh) using 15% ethyl acetate in petroleum ether as the eluent to afford Intermediate BE (300 mg, 38%) as a brown gum. ‘H NMR (CDCI3): delta 7.40-7.34 (m, 1H), 7.20-7.16 (m, 2H), 6.63 (bs, 1H), 3.76 (s, 2H), 3.04 (s, 3H). Mass (M-H): 187.0

The synthetic route of 4623-24-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HERCULES TECHNOLOGY MANAGEMENT CO V, INC.; BLAGG, Julian; WO2011/47156; (2011); 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. 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile, A new synthetic method of this compound is introduced below., SDS of cas: 243128-37-2

Example 59A 4-(4-trans-amino-cyclohexyloxy)-3-methoxy-benzonitrile To a stirred solution of trans-4-aminocyclohexanol (115 mg, 1 mmol) in DMF (5 mL) at 0 C. was added 60% NaH in mineral oil (120 mg, 3 mmol). The reaction mixture was stirred at 0 C. for 1/2 hour and then 4-fluoro-3-methoxy-benzonitrile (182 mg, 1.2 mmol) was added. It was heated to 60 C. for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) m/z 247 (M+H)+.

The synthetic route of 243128-37-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2004/259843; (2004); A1;; ; Patent; Madar, David J.; Djuric, Stevan W.; Michmerhuizen, Melissa J.; Kopecka, Hana A.; Li, Xiaofeng; Longenecker, Kenton L.; Pei, Zhonghua; Pireh, Daisy; Sham, Hing L.; Stewart, Kent D.; Szczepankiewicz, Bruce G.; Wiedeman, Paul E.; Yong, Hong; US2005/215784; (2005); 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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H3FN2O2

[0224] To a solution of 4-fluoro-3-nitrobenzonitrile (74.1 mg, 0.446 mmol) and l-(thiophen-2- yimethyl)piperazine (0.081 g, 0.446 mmol) in ACN (1 mL) was added K2CO3 (0.185 g, 1.338 mmol) The reaction mixture was heated to 80¡ãC for 3 hours and then diluted with water (3 mL). The liquid phase was decanted and the solid phase was washed with water and dried in a vacuum oven at 70¡ãC for 4 hours to give the title compound, which was used without further purification.

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; TAKEDA PHARMACEUTICAL COMPANY LIMITED; GREEN, Jason; HOPKINS, Maria; JONES, Benjamin; KIRYANOV, Andre A.; KUEHLER, Jon; MONENSCHEIN, Holger; MURPHY, Sean; NIXEY, Thomas; SUN, Huikai; (300 pag.)WO2018/183145; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6575-00-4, name is 3,5-Dichlorobenzonitrile, 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 6575-00-4, name: 3,5-Dichlorobenzonitrile

A 100 ml round bottom flask was charged under a stream of nitrogen with 3,5-dichlorobenzonitrile (R-3a,7.0 g, 40.69 mmol) and anhydrous DMF (75 mL). To the solution was added sodium methoxide (2.26 g, 44.76 mmol) and resulting solution was stirred further at RT for 24 h. When the reaction was complete, aqueous 10% HCl added dropwise to the reaction vessel. The crude mixture was extracted with EtOAc and sequentially washed with aqueous acid, water and brine. The EtOAc extracts were dried (Na2SO4), filtered and the solvent was removed in vacuo to afford a crude solid which was recrystallized from hexane/acetone to afford 5.9 g (86%) of 5-chloro-3-methoxy-benzonitrile.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,5-Dichlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Roche Palo Alto LLC; US2008/249151; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 3695-84-9, name is Methyl 2-cyano-3-phenylacrylate, 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 3695-84-9, Quality Control of Methyl 2-cyano-3-phenylacrylate

General procedure: To a mixture of alkene 1 (0.5 mmol), aldehyde 2 (2.5 mmol), and FeCl2 (1.6 mg, 0.0125 mmol), acetonitrile (3.0 mL) was added under nitrogen at room temperature. Then tert-butyl hydroperoxide 3 (TBHP, 2.0 mmol, 5-6 M in decane) was dropped into the mixture under nitrogen at room temperature. The resulting mixture was stirred under 85 oC for 1 h. The temperature of reaction was cooled to room temperature. The resulting reaction solution was directly filtered through a pad of silica by ethyl acetate. The solvent was evaporated in vacuo to give the crude products. NMR yields are determined by 1H NMR using dibromomethane as an internal standard. Solvent was evaporated and the residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether as eluent to afford the pure product 4.

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:
Article; Liu, Kaisheng; Li, Yuanming; Zheng, Xiaojian; Liu, Weiping; Li, Zhiping; Tetrahedron; vol. 68; 50; (2012); p. 10333 – 10337;,
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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 50712-68-0 as follows. COA of Formula: C8H6ClN

Magnesium turnings (0.224 g, 9.35 mmoi) were added to a three neck RBF equipped with nitrogen flow and cold water condenser. Anhydrous THF (25 mL) was added to the reaction mixture and heated at 70-80 C. A solution of 1 -bromo-4-methy3benzene (0.80 g, 4,67 mmol) in THF (10 mL) was added over 20 minutes dropwise to the reaction mixture and the resulting mixture was retluxed at 80 C for 2 h. The resulting gray mixture was cooled to 10 C and used in next step without further purification.(e) (4-chloro-2-methylphenyl)(p-tolyl)methanammeTo a solution of 4-chloro-2~methylbenzonitrile (0.50 g, 3.31 mmoi) in anhydrous THF (15 mL) at 0 C was added solution of >-tolylmagnesium bromide in THF (15 mL) slowly over 10 minutes and the resulting mixture was allowed to warm to rt. The reaction mixture was stirred at rt for 5 h and heated to 60 C where it was further stirred for 2 h. After completion of the imine formation, the reaction mixture was cooled to 0 C and 5 mL of methanol was added very slowly followed by sodium borohydride (0.244 g, 6.62 mmol). The resulting mixture was warmed to rt and stirred overnight. After completion of the reaction, water (10 mL) was added in to the reaction mixture and the mixture was extracted with ethyl acetate (2 X 40 mL). The combined organic layers were washed with brine (25 mL), dried over Na2804, and evaporated to obtained a crude product which was purified using silica gel column chromatography using 10% ethyl acetate in hexanes to obtain the title compound (0.40 g, 40.0%) as a light brown oil. ]H NMR (400 MHz, DMSO-de) delta ppm 7.54-7.56 (d, 1 H), 7.22-7.28 (d, 1 H), 7.15-7.21 (m, 3 H), 7.1 1 -7.13 (m, 2 H), 5.16 (s, 1 IT), 2.24 (s, 3 H), 2.21 (s, 3 IT).

According to the analysis of related databases, 50712-68-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TEMPERO PHARMACEUTICALS, INC.; BALOGLU, Erkan; GHOSH, Shomir; LOBERA, Mercedes; SCHMIDT, Darby, R.; WO2013/19635; (2013); A1;,
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