Tag: M.W=100-200

Electric Literature of 1897-52-5, 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. 1897-52-5, name is 2,6-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Take 2 L four bottles, add 600 mL of 60% sulfuric acid, electric stirring by adding 2,6_ difluorobenzonitrile 139.0 g (1.0 mol). Under N2 protection, the control reaction temperature was below 35 C, and 250 mum g of KBr03 (1.5 mol) was added to 10 batches. TLC monitoring, reaction 5-6 days, until the raw material point disappears, stop the reaction, the preparation of 800 mL 20% ice salt solution, the reaction solution Into the ice salt. After the product settling, the rapid filtration, the orange crude products, with CC14 dissolved crude products, respectively, with 5% Of NaHS03 solution, saturated Na2C03 solution and water to the solution was neutral, dried over anhydrous sodium sulfate, the solution was filtered, the water bath 60 C steamed to obtain light yellow liquid, rest for some time to cool into a pale yellow solid, vacuum distillation, warm water condensing steam, oil The bath was heated to 90 C and the fraction at a steam temperature of 58-62 C was cooled to give a white solid product in 71% yield

The synthetic route of 2,6-Difluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tianjin Normal University; Song, fanbo; Zhang, ZhongBiao; Li, huayun; Tang, hongying; Wang, ZhiJiang; Song, AiRu; (8 pag.)CN104017021; (2016); B;,
Nitrile – Wikipedia,
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Application of 4513-77-3, These common heterocyclic compound, 4513-77-3, name is 2-Oxocyclohexanecarbonitrile, 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.

a. Preparation of 3-amino-2-(4-chlorophenyl)-4,5,6,7-tetrahydro-2H-indazole A mixture of 3.6 parts of 4-chlorophenylhydrazine and 2.0 parts of triethylamine in 20.0 parts of toluene was stirred at room temperature for fifteen minutes. To the mixture was added 2.5 parts of 2-cyanocyclohexanone, prepared from commercial 2-chlorocyclohexanone and potassium cyanide [von R. E. Meyer, Helv. Chim. Acta., 16, 1291 (1933)], and a few drops of acetic acid. After refluxing for two hours, followed by stirring at room temperature overnight, the reaction mixture was evaporated to remove toluene and was treated with water, extracted with diethyl ether, dried over anhydrous magnesium sulfate and concentrated. Recrystallization from ethanol/water gave 2.6 parts of the compound, m.p. 140-142.

The synthetic route of 4513-77-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4059434; (1977); A;,
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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. 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8H6FN

4-Hydroxy-piperidine (1.05 g) was dissolved in 7 ml_ MTBE and 5 ml_ THF. Potassium tert-butylate (1.43 g) was added and the mixture was heated to 50 0C for 30 min. After cooling to rt, 4-Fluoro-2-methyl-benzonitrile (1.32 g) was added in portions. After stirring at rt for 2 h the reaction was quenched with water. The phases were separated and the aqueous layer was extracted with ethyl acetate (3x 10 ml_). The combined organic layers were washed with brine (10 mL), dried with MgSpsi4 and concentrated to yield 1.92 g (94percent) 2-Methyl-4-(piperidin-4-yloxy)-benzonitrile. Mass (ESI) (C13Hi6N2O): calcd. 216, found 217 [M+H]+.

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; SANOFI-AVENTIS; WO2009/80335; (2009); 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. 1897-52-5, name is 2,6-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2,6-Difluorobenzonitrile

Example 2054-[2-(2,4-Diamino-quinazoIin-5-yloxy)-ethyl]-piperazine-l-carboxylic acid tert- butyl ester4-[2-(2-Cyano-3-fluoro-phenoxy)-ethyl]-piperazine-l-carboxylic acid tert-butyl ester t-butyl 4-(2-hydroxyethyl)piperazine-l-carboxylate (0.6 g; 2.6 mmol) was added to a suspension of sodium hydride (125 mg; 3.1 mmol) in 5 mL of anhydrous dimethylformamide at O0C. Mixture was then heated to 4O0C for 2 hours. Anion was cooled to room temperature and added to a O0C mixture of 2,6-difluorobenzonitrile in 5 mL of dimethylformamide. After 16 hours at room temperature, reaction was quenched over 2Og of ice, mixture was extracted 4 X 50 mL with ethyl acetate. Combined organics was washed with 6 X 40 mLs water, brine and dried over MgSO4. Crude oil was obtained after filtration and concentration. Material was purified by flash chromatography using 2-3.5% methanol/dichloromethane gradient to obtain 660 mg of title compound. (73% yield).

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; deCODE Chemistry, Inc.; WO2008/16973; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 117482-84-5,Some common heterocyclic compound, 117482-84-5, name is 3-Chloro-4-fluorobenzonitrile, molecular formula is C7H3ClFN, 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.

3.49 g (20 mmol) 3-Boc-amino-propylamine in 5 ml DMF are combined with 2.75 ml (25 mmol) NMM. After the addition of 3.11 g (20 mmol) 3-chloro-4-fluoro-benzonitrile the mixture is stirred for 3.5 hours at ambient temperature under a nitrogen atmosphere, heated to 105 C. for 20 minutes and extracted with ethyl acetate. The combined organic phases are washed with water and sat. sodium chloride solution, dried over magnesium sulphate and evaporated down i. vac. The residue is further reacted without any more purification. Yield: 5.50 g (89%) C15H20N3O2 (309.80) Mass spectrum: (M+H)+=310/312 (chlorine isotope) Rf value: 0.40 (silica gel; petroleum ether/ethyl acetate=2:1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloro-4-fluorobenzonitrile, its application will become more common.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/203078; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, molecular formula is C7H5FN2, 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. Application In Synthesis of 5-Amino-2-fluorobenzonitrile

5-Amino-2-fluorobenzonitrile (1.50 g, 11.0 mmol) was dissolved in 10 mL of acetic acid.To this was added benzaldehyde (1.50 g, 14.1 mmol), and stirred at room temperature for 1 h.The reaction solution was cooled to 10-15 C, and sodium borohydride (0.44 g, 11.6 mmol) was added thereto.Stir for 10 min with heat, then alkalize with sodium carbonate solution, and extract with ethyl acetate.The organic layer was dried over anhydrous sodiumThe residue was recrystallized from ethyl acetate to give 5a, yield 80.2%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 53312-81-5, its application will become more common.

Reference:
Patent; Hangzhou Yirui Pharmaceutical Technology Co., Ltd.; Wang Xiaolu; Hu Yongzhou; Ye Qing; Hu Xiuai; (44 pag.)CN109651297; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 1897-52-5, 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. 1897-52-5, name is 2,6-Difluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 4: 2-[4-(2,6-Difluorophenoxy)cycIohexylmethoxy]-6- fluorobenzonitrile (Method I)4-(2,6-Difluorophenoxy)cyclohexylmethanol (100 mg; 0.4 mmol) and 2,6- difluorobenzonitrile were combined in 3 mL of dimethylformamide under nitrogen flow and chilled to O0C. Potassium t-butoxide (56 mg; 1.2 mmol) was added in portions. Mixture warmed to room temperature. After 4 hours reaction was quenched with 3 mL of water and mixture was extracted with 3 X 8 mL of ethyl acetate. Combined organics were washed with 5 X 8 mL of water, once with brine and dried over MgSO4. Crude oil was purified via flash chromatography using 0-20% ethyl acetate in hexanes to give 95 mgs of title compound. (66% yield).

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, 2,6-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; deCODE Chemistry, Inc.; WO2008/16973; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 243128-37-2, A common heterocyclic compound, 243128-37-2, name is 4-Fluoro-3-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.

Add lithium chloride (1.7 g, 40 mmol) to a stirred solution of 4-fluoro-3- methoxybenzonitrile (2.0 g, 13 mmol) in DMF (26 mL). Stir the resulting mixture at 160 C for 5 hours and then cool to room temperature with stirring for 12 hours. Dilute the mixture with ethyl acetate (50 mL) and wash with water (2 x 40 mL). Acidify the isolated aqueous phase with 1 M HC1 and extract with ethyl acetate (3 x 60 mL). Wash the combined organic extracts with water (2 x 100 mL), dry over Na2SC”4, and concentrate under reduced pressure to give the title compound as a yellow solid (0.68 g, 38%): ES/MS (m/z) 138 (M+H), which is directly 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; ELI LILLY AND COMPANY; LILLY CHINA RESEARCH AND DEVELOPMENT CO., LTD.; LIU, Kevin Kun-Chin; XIE, Yinong; WU, Liang; ZHOU, Guoqiang; WO2015/89800; (2015); A1;,
Nitrile – Wikipedia,
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326-62-5, name is 2-(2-Fluorophenyl)acetonitrile, 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. Product Details of 326-62-5

General procedure: To a stirring solution of substituted benzonitrile/phenylacetonitrile (1mmol) in anhydrous methanol (20mL) under N2 atmosphere was added hydroxylamine hydrochloride (1.2mmol). Triethylamine (2.5mmol) was added under continuous stirring condition and the mixture was then heated under reflux condition for overnight at 60C and continued until complete consumption of the starting material (monitored by TLC) [22,23]. The excess solvent was then removed under reduced pressure and the obtained residue was washed successively with water and brine, and extracted with ethylacetate (3×10mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. This reaction mixture was purified using silica gel column chromatography with a gradient solvent system of 10-20% ethylacetate to hexane to obtain the desired product with an average yield of 70-80%.

The synthetic route of 326-62-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Paul, Saurav; Roy, Ashalata; Deka, Suman Jyoti; Panda, Subhankar; Trivedi, Vishal; Manna, Debasis; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 364 – 375;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 54454-12-5, name is 3-Chloro-2-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 54454-12-5, Computed Properties of C8H6ClN

A. 3-Chloro-2-methylbenzaldehyde To 3-chloro-2-methylbenzonitrile (5 g, 33 mmol) in dichloromethane (150 mL) at -78 C. was added DiBAL (1M in dichloromethane, 41 mL). The reaction mixture was stirred at -78 C. for 2 h then quenched with methanol. The mixture was warmed to 0 C and HCl (10%) was added. The ice-water bath was removed and the mixture was stirred at room temperature for 10 min. The two phases were separated and aqueous phase was extracted with dichloromethane. Combined dichloromethane was washed with brine, dried over sodium sulfate and concentrated. Column chromatography (5% ethyl acetate/hexane) gave 3-chloro-2-methylbenzaldehyde (3.5 g, 69%). 1H NMR (300 MHz, CDCl3) delta 2.64 (s, 3H), 7.21-7.26 (m, 1H), 7.50-7.53(m, 1H), 7.63-7.66 (m, 1H), 10.20 (s, 1H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Chloro-2-methylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ALLERGAN, INC.; US2009/239918; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts