Tag: M.W=200-300

1953-99-7, 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. 1953-99-7 name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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.

Synthesis Example 4: Synthesis of 3,4,6-trichloro-5-(2,6-difluoro-phenoxy)-phthalonitrile 5 g of 3,4,5,6-tetrachlorophthalonitrile, 2.45 g of 2,6-difluorophenol, 3.9 g of K2CO3, and 25 ml of N,N-dimethyl formamide were put in s 100 ml flask, and then stirred while heated at 70¡ã C. When the reaction was complete, EA (ethyl acetate) was used for an extraction. After the extraction, the resultant was concentrated to obtain a solid. Herein, the obtained solid was dissolved in a small amount of dichloromethane, and then several times washed with hexane, filtered, and vacuum-dried to obtain 3,4,6-trichloro-5-(2,6-difluoro-phenoxy)-phthalonitrile.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; SAMSUNG SDI CO., LTD.; JEONG, Euisoo; SEO, Hyewon; SHIN, Myoungyoup; SHIN, Sunwoong; JUNG, Juho; HAN, Gyuseok; (25 pag.)US2018/335547; (2018); A1;,
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179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, 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. 179897-89-3

5-bromo-2-fluorobenzonitrile (1.0 g, 5.0 mmol) was weighed and dissolved in DMF (10 mL), Add K2CO3 (2.1 g, 15.0 mmol), stir at room temperature for 1.0 h, add N-methylisobutylamine (1.3 g, 15.0 mmol), and react at 80 C for 3 h. TLC followed the reaction completely.Cooled to room temperature, diluted with 100mL of water was added, ethyl acetate (100mL ¡Á 3). The combined organic phases were washed with brine, dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, purification by silica gel column (V ethyl acetate: V petroleum ether = 1: 20) afforded 5-bromo-2-isobutylmethylaminobenzonitrile (a10)1.27 g, yield 95%

Statistics shows that 179897-89-3 is playing an increasingly important role. we look forward to future research findings about 5-Bromo-2-fluorobenzonitrile.

Reference:
Patent; South China University of Technology; Li Jing; Li Xiaolei; Li Yuanyuan; Zhou Haiyan; Zhang Lei; Guan Su; (21 pag.)CN110078668; (2019); A;,
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A common heterocyclic compound, 1897-41-2, name is 2,3,5,6-Tetrachloroterephthalonitrile, molecular formula is C8Cl4N2, 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. 1897-41-2.

0.60 g (0.015 mol) of sodium hydroxide was added to a solution of 1.22 g (0.0075 mol) of 3,5-dichloropyridin-4-amine in 40 mL of DMF, followed by addition of 2 g (0.0075 mol) of 2,3,5,6-tetrachloroterephthalonitrile under stirring, the mixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatography monitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phase was washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling point range 60-90¡ã C.)=1:3, as an eluent) to give 2.16 g of compound C-124 as yellow solid, m.p. 202-204¡ã C. [0197] 1H-NMR (300 MHz, internal standard TMS, solvent CDCl3) delta (ppm): 7.28 (br, 1H, NH), 8.30 (s, 2H, Py-2,6-2H).

The synthetic route of 2,3,5,6-Tetrachloroterephthalonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHENYANG RESEARCH INSTITUTE OF CHEMICAL INDUSTRY CO., LTD.; SINOCHEM CORPORATION; Liu, Changling; Huang, Guang; Lan, Jie; Hao, Shulin; Li, Zhinian; Li, Huichao; Guan, Aiying; Jiang, Airu; Xu, Ying; US2014/213598; (2014); A1;,
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27126-93-8,Some common heterocyclic compound, 27126-93-8, name is 3,5-Bis(trifluoromethyl)benzonitrile, molecular formula is C9H3F6N, 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.

Example 15 Synthesis of 5-(3,5-bis(trifluoromethyl)phenyl)-1H-tetrazole (8) Anhydrous zinc bromide (93.5 g, 415 mmol, 0.99 equiv.), sodium azide (29.8 g, 458 mmol, 1.1 equiv.) and water (750 ml) were added to 3,5-bis(trifluoromethyl)benzonitrile (100.0 g, 418 mmol, 1.00 equiv.). The resulting suspension was stirred for 10 days at ambient temperature. The completion of the reaction was confirmed by reversed phase HPLC on a Waters Novapak C18 column (3.9*150 mm) eluding with a linear gradient from 40% to 100% acetonitrile in 250 mM triethylammonium acetate buffer pH 6.5 in 15.00 minutes with a flow rate of 1.0 mL/min, detection at lambda=270 nm, product retention time 2.0 min., educt retention time 6.5 min. Ethyl acetate (3.8 ltr.) and 10% citric acid in water were added and the resulting mixture was vigorously stirred for 15 minutes. The aqueous phase was separated and extracted with ethyl acetate (2*900 ml). The organic phases were combined and evaporated to dryness. The resulting solid was stirred in aqueous NaOH solution (0.25 M, 3.8 ltr.) for 30 minutes to give a suspension, which was filtered. The filtrate was acidified with aqueous HCl (375 ml conc. hydrochloric acid and 375 ml water) which caused the product to precipitate as a fine white powder. The product was collected by filtration after one hour, washed with cold hexanes (100 ml) and dried in a desiccator under vacuum, yield 72.7 g (62%) of compound (8) as white crystalline powder. The purified product had a purity of 100% by reversed phase HPLC as depicted in . 1H NMR (300 MHz, d6-DMSO) delta 8.26 (s, 1H), 8.59 (s, 1H), m.p. 179 C. The product can be recrystallized from toluene.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Bis(trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Patent; Sigma-Aldrich Co.; US2006/247431; (2006); A1;,
Nitrile – Wikipedia,
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The chemical industry reduces the impact on the environment during synthesis 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, I believe this compound will play a more active role in future production and life. 1953-99-7

Synthesis Example 1: Synthesis of 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile 5 g of 3,4,5,6-tetrachlorophthalonitrile, 3.21 g of 2-phenylphenol, 3.9 g of K2CO3, and 25 ml of acetone were put in a 100 ml flask, and then stirred while heated at 70¡ã C. When the reaction was complete, the resultant was filtered and washed with acetone, and a liquid therefrom was distillated to obtain a solid. Herein, the obtained solid was dissolved in a small amount of dichloromethane, and then several times washed with hexane, filtered, and vacuum-dried to obtain 4-(biphenyl-2-yloxy)-3,5,6-trichloro-phthalonitrile.

The chemical industry reduces the impact on the environment during synthesis 1953-99-7. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SAMSUNG SDI CO., LTD.; JEONG, Euisoo; SEO, Hyewon; SHIN, Myoungyoup; SHIN, Sunwoong; JUNG, Juho; HAN, Gyuseok; (25 pag.)US2018/335547; (2018); A1;,
Nitrile – Wikipedia,
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The chemical industry reduces the impact on the environment during synthesis 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, I believe this compound will play a more active role in future production and life. 52133-67-2

To the 250 mL round bottomed flask containing 14.2 g (61.8 mmol) of ethyl 2,2-diethoxy cyanoacetate was added 110 mL of absolute ethanol followed by 28 mL of sodium ethoxide (21percent, 75.0 mmol). Thiourea (5.7 g, 74.5 mmol) was added all at once and the mixture was heated to 95¡ãC and refluxed overnight. The mixture was then cooled to room temperature and concentrated. Water (250 mL) was added and the aqueous layer was washed with diethyl ether (3 x 250 mL). The aqueous layer was then neutralized with acetic acid (1 eq.) and the precipitate was filtered. The yellow solid was dried under vacuum over P2O5 overnight to give 9.2 g (35.5 mmol, 57percent) of crude product. 1H-NMR (DMSO, 600 MHz): sigma 1.07 (t, 6H, J = 7.2 Hz), 2.43 (d, 2H, J = 5.4 Hz), 3.37 – 3.43 (m, 6H), 3.56 – 3.61 (m, 2H), 4.50 (t, 1H, J = 5.4 Hz), 6.07 (s, 2H), 11.5 (br s, 1H), 11.7 (br s, 1H). 13C-NMR (DMSO, 150 Mz): sigma 15.4, 27.9, 61.9, 85.7, 101.7, 151.9, 161.8, 172.9. HRMS (FAB): expected for C10H18N3O3S (M+H)+: 260.10634. Found: 260.10640. IR(neat): vmax 3342, 3219, 2973, 2879, 1563 cm-1.

The chemical industry reduces the impact on the environment during synthesis 52133-67-2. I believe this compound will play a more active role in future production and life.

Reference:
Article; Kim, Jiae; Wang, Ligong; Li, Yongfeng; Becnel, Kimberlynne D.; Frey, Kathleen M.; Garforth, Scott J.; Prasad, Vinayaka R.; Schinazi, Raymond F.; Liotta, Dennis C.; Anderson, Karen S.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 12; (2012); p. 4064 – 4067;,
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These common heterocyclic compound, 134521-16-7, name is 4,4′-Dicyanobenzhydrol, 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. 134521-16-7

EXAMPLE 1 This example demonstrates a method for preparing bromo-bis-(4-cyanophenyl)-methane. A three-necked round-bottom flask equipped with a mechanical stirrer, a nitrogen inlet and a Dean Stark apparatus was charged with bis-(4-cyanophenyl)-methanol (60 g, 0.256 mole) and toluene (360 ml) and the reaction mixture was heated to 60 C. HBr (48%, 54 ml, 1.8 eq.) was added in one portion and the reaction mixture was refluxed for two hours, during which time water was removed by azeotropic distillation. The reaction mixture was cooled to 70 C., water was added (250 ml), and stirring was maintained for 5 minutes. The two resulting layers were separated, the aqueous phase was washed with toluene (50 ml), and the organic layers were combined and washed with an aqueous solution of 5% potassium carbonate (200 ml), then with water (250 ml). Toluene was distilled off under reduced pressure (about 290 ml) and the solution was cooled to 40 C. Hexane was added (240 ml) and the mixture was cooled to room temperature and stirring was maintained for about 18 hours. The crude solid product was obtained by filtration (70.3 g) in 92% yield, having a purity of 99% (by HPLC).

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 134521-16-7.

Reference:
Patent; CHEMAGIS LTD.; US2007/112202; (2007); 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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate, A new synthetic method of this compound is introduced below., 79463-77-7

6.1 To a solution of 4-(2-keto-1-benzimidazolinyl)piperidine (1.3 g; 5.98 mmol) in acetonitrile was added diphenyl N-cyanocarbonimidate (1.56 g; 6.55 mmol; 1.1 equiv). The reaction mixture was stirred at 60 C. for 48 h under nitrogen atmosphere and then concentrated under reduced pressure. The crude product was suspended in ethyl acetate (50 mL) and a saturated aqueous solution of sodium bicarbonate (50 mL) and stirred overnight at room temperature. The solid was collected by filtration and dried to give N-cyano-4-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboximidic acid phenyl ester (1.85 g; 85%) as a white solid.

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; Icagen, Inc.; US2003/171360; (2003); A1;,
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17216-62-5, 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. 17216-62-5, name is Diethyl 2-(2-cyanoethyl)malonate, A new synthetic method of this compound is introduced below.

241 kg of the above intermediate, 1200 kg of isopropyl alcohol and 28 kg of catalyst Raney Co were placed in a 2-liter stainless steel autoclave. After replacing the air in the kettle with hydrogen,Press the hydrogen pressure to 25kg/cm2, turn on the stirring, and slowly raise the temperature to 70 C with jacketed steam.Above, the oxygen inhalation reaction begins to exotherm. At this point, turn on the cooling water to cool.The reaction temperature was controlled to rise smoothly to 90-100 C, and the introduction of hydrogen gas was controlled to stabilize the pressure at 35-40 kg/cm 2 .After 4.5 hours, the hydrogen absorption was stopped and the reaction was continued at 100 C, 35 kg / cm 2 for 1 hour.The material in the autoclave was cooled to 44 C with cooling water, and after the residual hydrogen pressure was vented,Press the material to the filter with N2 gas.The Raney Co catalyst was recovered by filtration under N2 gas protection.The filtrate was introduced into a 2000 liter glass-line distillation crystallization kettle, and heated under stirring.The solvent isopropanol was distilled off. Then add 660 kg of petroleum ether while stirring for 0.5 hour.The crystals are gradually cooled, and the stirring is intermittently started to prevent the product from being easily discharged from the bottom of the kettle after agglomeration. After the completion of the crystallization, the mixture was centrifuged and dried to give 184 kg of a white solid. The content of HPLC detection was 99.6%, and the hydrogenation reaction yield was 96.4%.The total yield of the two-step reaction was 79.2%.

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; Shanghai Jingwei Chemical Technology Co., Ltd.; Yao Husheng; Zhao Zhulin; Zhang Ming; Chen Bo; (6 pag.)CN108484484; (2018); A;,
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1953-99-7, A common compound: 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

In a 100 ml flask, 3,4,5,6-tetrachlorophthalonitrile (5 g), 2-phenylphenol (3.201 g), K2CO3 (3.898 g)And acetonitrile (50 ml), and reflux while heating. After completion of the reaction, the mixture was filtered, washed with tetrahydrofuran (THF)The resulting solid was dissolved in a small amount of dichloromethane and then hexane was added thereto to obtain a solid (4- (biphenyl-2-ylamino) -3,5,6-trichlorophthalonitrile). At this time, the obtained solid was washed several times, filtered and vacuum dried.

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, 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cheil Industries Co., Ltd.; Choe, Say Young; Kwon, JaeYoung; Park, Uhn B; Lee, Jong Son; Lee, Chang Ryul; Jong, Ju Ho; Choe, Mi Jin; Choe, Sung Gip; Hyung, Gyung Hee; (28 pag.)KR2015/130131; (2015); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts