Tag: M.W=100-200

Synthetic Route of 64248-64-2,Some common heterocyclic compound, 64248-64-2, name is 2,5-Difluorobenzonitrile, molecular formula is C7H3F2N, 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 A: Thio-Amide Synthesis:1-1 1 -2A stirred solution of the appropriate benzonitrile e.g., 2,5-difluorobenzonitrile (1-1), (15 mmol) in pyridine (10 rnL) was treated with sulfide (20% wt solution in water, 16.5 mmol) and triethyl amine (16.5 mmol). The reaction mixture was stirred at 500C for 5 hr until the reaction was complete. After cooling to RT, the mixture was diluted with cold water. Extracted with EtOAc, and the organics separated, then washed with H2O (x3), sat. brine (x3), then dried (Na2SO4), filtered, and evaporated under reduced pressure to give the crude. Purification on silica gel column (20% ethyl acetate/hexane) to afford thio-amide as yellow solid, 1-2 (yield 88.5%). 1H NMR (300 MHz, CDCl3): delta 7.12 (m, 2 H), 7.90 (br, 2 H), 8.08 (m, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,5-Difluorobenzonitrile, its application will become more common.

Reference:
Patent; NOVARTIS AG; WO2008/63912; (2008); A1;,
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Electric Literature of 1080-74-6, 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 1080-74-6 as follows.

A solution of intermediate 67 (135 mg, 0.130 mmol) in chloroform (10 cm3) and pyridine (0.75 cm3) is degassed for 10 minutes with nitrogen. 2-(3- Oxo-indan-1 -ylidene)-malononitrile (180 mg, 0.91 mmol) is added in one portion and the reaction mixture is stirred at 23 C for 150 minutes. Methanol (15 cm3) is added and the obtained precipitate is collected by filtration and washed with methanol (3 x 10 cm3). The solid is filtered through a pad of silica (40-60 petrol:dichloromethane; 2:3). Concentration in vacuo followed by trituration in refluxing acetone (20 cm3) and then in a 3:1 mixture of acetone:chloroform (40 cm3) gives compound 1 15 (144 mg, 79%) as a dark blue powder. 1H NMR (400 MHz, CDCIs) 8.84 (2H, s), 8.61 – 8.67 (2H, m), 7.84 – 7.90 (2H, m), 7.63 – 7.72 (6H, m), 7.13 – 7.21 (8H, m), 6.83 – 6.90 (8H, m), 3.81 (4H, m), 3.72 (4H, m), 1 .78 – 1 .92 (4H, m, J 6.6), 1 .56 (4H, m), 1 .26 (4H, m), 1 .00 (12H, d, J 6.7), 0.94 (12H, t, J 7.5).

According to the analysis of related databases, 1080-74-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; NANSON, Lana; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (327 pag.)WO2018/65350; (2018); A1;,
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Electric Literature of 63069-50-1, 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 63069-50-1 as follows.

General procedure: As shown in FIG. 1, the raw material 1 (acidic liquids of aniline) and raw material 2 (NaNO2 aqueous solution with mass concentration of 20%) were fed to temperature section 1 with constant-flow pump, and the diazotization of aniline completed while the materials flowed past the temperature section 1. The raw material 3 (Na2SO3 aqueous solution with mass concentration of 19%) was fed to temperature section 2 with constant-flow pump for preheating, then mixed with diazonium salt formed through temperature section 1 in temperature section 3, flowed through temperature section 3 until the reaction was completed. The reaction solution from temperature section 3 flowed into temperature section 4 after mixed with raw material 4 (acid), and the reaction completed while flow through temperature section 4. The reaction mixture was collected, crystallization by cooling the temperature, after filtration and drying to get the phenylhydrazine salts product. Reaction parameters and results were as follows:

According to the analysis of related databases, 63069-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SHANGHAI HYBRID-CHEM TECHNOLOGIES; MA, Bing; Pan, Shuai; (35 pag.)US2019/152896; (2019); A1;,
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Application of 16588-02-6, 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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2-chloro-5-nitrobenzonitrile (2g,1 eq,10.96mmol), potassium carbonate (4.54g, 3eq, 32.7001), piperidine (1 ¡¤ 63 mL, 1.5 eq, 16.34 mmol) and DMF (5 mL) at 90 C Should be 3h, until the reaction is complete, remove the oil bath. DMF was diluted with 100 mL EA, washed with saturated ammonium chloride and sodium chloride respectively. The aqueous phase was extracted again with ethyl acetate. The organic phases were combined and dried over anhydrous sodium sulfate. The filtrate was concentrated to give a yellow solid (Compound 10) 2.528 g, yield 99%

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

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Xu Zhongliang; Wang Heyao; Cai Mengxin; (31 pag.)CN106892871; (2017); A;,
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Electric Literature of 170572-49-3, 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. 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-fluoro-4-methylbenzonitrile (29.54 g) and NBS (46.7 g) as a suspension in 1,2-dichloroethane (500 ml) was treated with benzoyl peroxide (4.24 g) in a flask mounted with a reflux condenser open to air. The flask was immersed in an oil bath at 75 C and light shun on it with a sunlamp. A more vigorous reflux was suddenly observed and the reaction became homogeneous. The reaction was let stir at this temperature for a total of 2 hours then let cool to room temperature. Hexanes (500 ml) was added and the precipitate filtered and discarded. The filtrate was concentrated under reduced pressure to approximately 100 ml and taken up in ethyl acetate (200 ml). The reaction was washed with half saturated sodium bicarbonate (100 ml), then brine (100 ml). The organic layer was separated and dried over magnesium sulfate. The organic phase was concentrated under reduced pressure to give the benzylic bromide as a yellow solid that was used as such in the next step.

The chemical industry reduces the impact on the environment during synthesis 3-Fluoro-4-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2009/67797; (2009); A1;,
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Related Products of 53312-81-5, 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. 53312-81-5, name is 5-Amino-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

j1211] Compound 326 was synthesized from 5-amino-2- fluorobenzonitrile (47.2 mg, 0.346 mmol) which was stirred in dichloromethane (2 mE) and 0.50 mE saturated sodium bicarbonate solution at 0 C. Phosgene (20% in toluene, 0.495 mE, 0.693 mmol) was added and stirred for 30 mm. The organic layer was extracted with dichloromethane and washed with water followed by sodium bicarbonate solution. The organic layer was concentrated and redissolved in DMF (2 mE). Corresponding compound C (100 mg, 0.144 mmol) and TEA (95 IL, 0.6 93 mmol) was added and heated at 90 C. for 1 h. The crude product was purified with reverse phase colunm (water:CAN 1:1) to afford the target compound as a light brown solid (47.8 mg, 38.7%); 1H NMR (400 MHz, Chioroform-d) oe 0.92 (d, J=6.6 Hz, 3H), 1.16 (d, J=6.6 Hz, 3H), 1.25 (d, J=6.6 Hz, 3H), 1.71-1.83 (m, 1H), 2.00-2.08 (m, 1H), 2.10-2.18 (m, 2H), 2.25-2.44 (m, 2H),2.80-3.04 (m, 4H), 3.26-3.46 (m, 3H), 3.68-3.86 (m, 3H),4.38-4.69 (m, 6H), 4.78 (d, J=11.3 Hz, 1H), 4.92-5.05 (m, 1H), 5.07-5.18 (m, 1H), 5.36 (t, J=7.5 Hz, 1H), 5.77 (d, J=7.6 Hz, 1H), 6.54-6.68 (m, 3H), 7.05 (t, J=8.7 Hz, 1H), 7.39 (d, J=9.5 Hz, 1H), 7.48-7.56 (m, 1H), 7.72-7.81 (m, 1H), 8.15 (s, 1H), 8.47 (d, J=9.7 Hz, 1H); ESI-MS: [m/z+ H]=855.46.

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, 5-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; St. Jude Children’s Research Hospital; Lee, Richard E.; Zhao, Ying; Jiuyu, Liu; (323 pag.)US2018/79784; (2018); 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. 1194-02-1, name is 4-Fluorobenzonitrile, A new synthetic method of this compound is introduced below., name: 4-Fluorobenzonitrile

General procedure: To a stirred suspension of corresponding nitrile and hydroxylamine hydrochloride (1.5 equiv.) in EtOH (10 mL per gram of nitrile) a NaHCO3 (1.5 equiv.) was added. The reaction mixture was stirred under reflux for a 6 h. After the reaction had completed, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with cold water (200 mL). The resulting precipitate was filtered off and washed with cold water (50 mL).

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:
Article; Presnukhina, Sofia; Tarasenko, Marina; Baykov, Sergey; Smirnov, Sergey N.; Boyarskiy, Vadim P.; Shetnev, Anton; Korsakov, Mikhail K.; Tetrahedron Letters; vol. 61; 9; (2020);,
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These common heterocyclic compound, 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, 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. SDS of cas: 1009-35-4

To a flask charged with 4-fluoro-3-nitrobenzonitrile (0.984 g, 5.92 mmol) in ACN (19.75 mL), was added trans-n-boc- 1 ,4-cyclohexanediamine (1.269 g, 5.92 mmol) and TEA (1.651 mL, 1 1.85 mmol). The resulting mixture was stirred at 80¡ãC for 3 h leading to complete conversion. The mixture was cooled to RT. The resulting solid was filtered, washed with water and dried to give tert-butyl ((lr,4r)-4-((4- cyano-2-nitrophenyl) amino)cyclohexyl)carbamate (1.93 g, 5.36 mmol, 90 percent yield) as yellow solid, which was used for next step without further purification. lH NMR (400 MHz, DMSO-i/6) delta ppm 8.29 – 8.37 (m, 1 H) 7.96 – 8.10 (m, 1 H) 7.53 – 7.71 (m, 1 H) 7.13 (d, J=9.29 Hz, 1 H) 6.64 (d, J=7.82 Hz, 1 H) 3.34 – 3.62 (m, 1 H) 3.09 (d, J=2.25 Hz, 1 H) 1.81 (d, J=10.27 Hz, 2 H) 1.65 (d, J=10.47 Hz, 2 H) 1.09 – 1.38 (m, 13 H). m/z (ESI) 361.2

The synthetic route of 4-Fluoro-3-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John L.; CHAKKA, Nagasree; DIMAURO, Erin F.; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Xin; WO2014/36022; (2014); 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. 6629-04-5, name is N-Cyanoacetylurethane, A new synthetic method of this compound is introduced below., Recommanded Product: 6629-04-5

EXAMPLE 1 A mixture of N-ethoxycarbonylcyanoacetamide (42 g), triethylorthoformate (40 g) and acetic anhydride (100 ml) is heated at reflux for one hour. The reaction is allowed to stand until cool and then is filtered, washing with ether, to yield alpha-cyano-beta-ethoxy-N-ethoxycarbonylacrylamide.

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; Zoecon Corporation; US4358591; (1982); A;; ; Patent; Zoecon Corporation; US4411839; (1983); A;; ; Patent; Imperial Chemical Industries Limited; Zoecon Corporation; US4307098; (1981); A;,
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Application of 1558-81-2, 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. 1558-81-2, name is Ethyl 1-Cyano-1-cyclopropanecarboxylate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To concentrated sulfuric acid (102 mL) was added 1-cyano-cyclopropanecarboxylic acid ethyl ester (60 g, 0.43 mol) dropwise followed by 2-methylpentan-2,4-diol (52 g, 0.44 mmol) dropwise at 0 C. The mixture was stirred for an additional 1 h at 0 C. then poured onto ice-water. The aqueous phase was washed with AcOEt (3¡Á200 mL) and then basified to pH 12 with 10 M NaOH. The resulting mixture was extracted with EtOAc (3¡Á500 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel to give 1-(4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazin-2-yl)-cyclopropanecarboxylic acid ethyl ester (65 g, yield: 63.2%). 1H NMR (CDCl3 400 MHz): delta4.21-4.06 (m, 311), 1.73-1.69 (m, 1H), 1.40-1.10 (m, 1711)

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, Ethyl 1-Cyano-1-cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; H. Lundbeck A/S; Kilburn, John Paul; Rasmussen, Lars Kyhn; Jessing, Mikkel; Eldemenky, Eman Mohammed; Chen, Bin; Jiang, Yu; Hopper, Allen T.; US2014/107340; (2014); A1;,
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