Tag: M.W=100-200

These common heterocyclic compound, 218632-01-0, name is 3-Fluoro-4-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. category: nitriles-buliding-blocks

[0245] A mixture of 3-fluoro-4-mtrobenzonitrile (2.85 g, 17.13 mmol), 4-(2,4- difluorophenoxy)piperidine, HC1 (3.889 g, 15.58 mmol), and ACN (19.47 mL) was heated to 80C and stirred for 12 hours, then filtered and concentrated in vacuo to afford nitro- intermediate 3-(4-(2,4-difluorophenoxy)piperidin-l-yi)-4-nitrobenzonitrile. Tlie (crude) nitro- intermediate was taken up in a 1 : 1 mixture of THF and Me OH (0.17 M, 90 mL). Ammonium chloride (12.50 g, 234 mmol) and zinc (15.28 g, 234 mmol) were added and the reaction mixture was stirred at RT for 2 hours, then filtered and concentrated in vacuo. The concentrate was diluted with water, basified with 1 M (aq) NaOH, extracted with EtOAc, dried over Na?.S04, filtered, and concentrated in vacuo to give the title compound as a viscous brown oil that solidified after 2 days (4.815 g, 94%).

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

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: 6574-99-8, name is 3,4-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 6574-99-8, Application In Synthesis of 3,4-Dichlorobenzonitrile

The solvent and catalyst recovered in Example 2 were used for feeding.1) In the reaction kettle with a reflux water separation device, add the anhydrous aprotic polar solvent 1,3-dimethylimidazoline used in Example 2 and make up 2000 kg with a new solvent.Raw materials 3,4-dichlorobenzonitrile 1000 kg, water agent 200 kg toluene, heated to 90 ~ 120 reflux, water separation for 1 to 2 hours, until the water in the kettle <0.05% 2) Add 800 kg of potassium fluoride and 45 kg of catalyst to the reaction kettle, raise the temperature to 130 150 , and reflux for 2 to 3 hours; 3) Turn on the vacuum pump, the vacuum degree is -0.1MPa, the top temperature of the reaction kettle tower is 90-115 C, and the toluene is collected, and the fractions are collected; 4) Continue to increase the temperature. When the temperature in the reactor reaches 190 200 and the top temperature reaches 170-180 , the crude 3,4-difluorobenzonitrile will be collected. When the content of 3,4-difluorobenzonitrile in the reactor is at At 89.0-89.5%, the reaction is deemed complete and the crude product is 818 kg; 5) Turn off the hot oil pump, turn on the cold oil system, the temperature in the reaction kettle drops below 100 C, put the materials in the reaction kettle into a centrifuge, the filtrate is pumped into the reaction kettle for the next feeding, and the solid materials are bagged; 6) The crude product 3,4-difluorobenzonitrile is drawn into the rectification kettle, stirring is started, and the fractions of 179-181 C are collected at elevated temperature and pressure to obtain the finished product 3,4-difluorobenzonitrile 743 kg, content 99.63%, yield 93.0%; after distillation, the residual liquid is sent to the reactor for the next feeding. At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3,4-Dichlorobenzonitrile, and friends who are interested can also refer to it. Reference:
Patent; Ji’ning Kangsheng Rainbow Biological Technology Co., Ltd.; Qian Jidong; Huang Dingqian; Sheng Rui; Yan Weiwei; (8 pag.)CN110804001; (2020); A;,
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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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, A new synthetic method of this compound is introduced below., Computed Properties of C3H7ClN2

Example 109(4S,5R)-3-(4-(4-chlorophenoxy)phenyl)-5-(chloromethyl)-4-(3-fluorophenyl)oxazolidin-2- one; [00174] To a solution of the mesylate, prepared using the methods described in example34 (35 mg, 0.07 mmol) and triethylamine (0.125 mL, 0.9 mmol) in DMF (0.3 mL) was added methylaminoacetonitrile hydrochloride (76 mg, 0.7 mmol). The reaction was heated to 90 ¡ãC and stirred for 3 h. After cooling, and dilution with water and ethyl acetate, the organic was washed successively with 1 M HCl, brine, dried over magnesium sulfate, filtered and concentrated. HPLC purification (0-90percent acetonitrile/water) gave 16 mg (53percent) of the title compound as a colorless oil. 1H NMR (acetone-d6) delta (ppm) 7.52-7.56 (m, 2H), 7.47 (ddd, IH, J = 8.1, 8.1, 6.0 Hz), 7.31-7.42 (m, 4H), 7.10-7.15 (m, IH), 6.95-6.99 (m, 4H), 5.55 (d, IH, J = 4.8 Hz), 4.75 (q, IH, J = 4.4 Hz), 4.10-4.17 (m, 2H). HPLC-MS calculated C22Hi6Cl2FNO3 (M+H+): 432.1, found: 432.1.

The synthetic route of 25808-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; WO2008/76754; (2008); A2;,
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Application of 2338-75-2, These common heterocyclic compound, 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, 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 solution of Intermediate 6a (2.0 g, 10.8 mmol) and carbon disulfide (0.71 mL, 11.8 mmol) in tetrahydrofuran (30 mL) is added dropwise to an ice cold solution of sodium hydride (950 mg of 60 % suspension in oil, 24 mmol) in tetrahydrofuran and stirred at room temperature for 3 hours. The mixture is cooled to 0 C, then methyl iodide (1.5 mL, 24 mmol) is added dropwise and stirred at room temperature for 12 hours. The mixture is poured into water andextracted with dichloromethane (2 x). The organic layers are combined, washed with brine, dried over MgSO4, filtered, concentrated and the crude material is purified by flash chromatography (hexanes/ethyl acetate gradient) to afford 3,3-bis(methylthio)-2-(4-(trifluoromethyl) phenyl)acrylonitrile I-14a.

The synthetic route of 2338-75-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Azimioara, Mihai; Alper, Phil; Cow, Christopher; Mutnick, Daniel; Nikulin, Victor; Lelais, Gerald; Mecom, John; McNeill, Matthew; Michellys, Pierre-Yves; Wang, Zhiliang; Reding, Esther; Paliotti, Michael; Li, Jing; Bao, Dingjiu; Zoll, Jocelyn; Kim, Young; Zimmerman, Matthew; Groessl, Todd; Tuntland, Tove; Joseph, Sean B.; McNamara, Peter; Seidel, H. Martin; Epple, Robert; Bioorganic and Medicinal Chemistry Letters; vol. 24; 23; (2014); p. 5478 – 5483;,
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Reference of 6629-04-5,Some common heterocyclic compound, 6629-04-5, name is N-Cyanoacetylurethane, molecular formula is C6H8N2O3, 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 solution of compound Al (3. 12g) and potassium carbonate (2.75g) in DMF (5OmL) is stirred at room temperature for 2 hours. 2.6mL carbon disulfide is added to the reaction suspension, and then kept stirring for 4 hours. After completion of the reaction, 100% ethanol is added to reaction mixture at 0C. Yellow precipitate is generated and filtered out. After washing with diethyl ether and drying under reduced pressure overnight, pale yellow solid, compound A2 is obtained in a yield of 92.3%. 1H-NMR (400MHz, DMSO-d6) 5 (ppm):14.92 (C3NHC4, s, 1H), 3.99 (C2H, q, J = 4.72Hz, 2H), 1.16 (C1H, t, J =4.72Hz, 3H). 13C- NMR (600MHz, DMSO-d6) 5 (ppm): 222.21 (C7), 164.35 (C4), 152.08 (C3), 125.16 (C6), 97.80 (C5), 59.09(C2), 14.50 (C1). HRMS (ESI) mlz calculated for C7H6N2O3S2K2+H308.9 172, found 308.9171. Formula is confirmed as C7H6N20352K2.

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

Reference:
Patent; RHODE ISLAND HOSPITAL; CHEN, Qian; YU, Hongchuan; CHEN, Yupeng; (123 pag.)WO2016/81522; (2016); A1;,
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Synthetic Route of 6621-59-6, 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. 6621-59-6, name is 6-Bromohexanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: K2CO3, KOH and TBAB were added to a solution of each triazole compound (7a-c) in ACN. Each solution was stirred for 30 min at room temperature; alkyl bromide was added, and the reaction proceeded for 3-24 h at room temperature. The solid was filtered and then washed with diethyl ether. The solvent of the filtrate was removed in vacuo and purified by silica gel column chromatography (hexane/ethyl acetate) to yield the desired compound or crude mixture, which were reacted in the next step of deprotection.

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

Reference:
Article; Lee, Sun-Mi; Yoon, Kyoung Bin; Lee, Hyo Jeong; Kim, Jiwon; Chung, You Kyoung; Cho, Won-Jea; Mukai, Chisato; Choi, Sun; Kang, Keon Wook; Han, Sun-Young; Ko, Hyojin; Kim, Yong-Chul; Bioorganic and Medicinal Chemistry; vol. 24; 21; (2016); p. 5036 – 5046;,
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Some common heterocyclic compound, 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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. HPLC of Formula: C7H3ClN2O2

1) Production of 4-isobutoxy-3-nitrobenzonitrile 19.5 g of 4-chloro-3-nitrobenzonitrile was dissolved in 200 ml of DMF, and after 16.0 g of 2-methyl-1-propanol, 30 g of potassium carbonate and 7.1g of potassium iodide were added thereto, the mixture was heated and stirred at 80C for 24 hours. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated saline solution and dried over magnesium sulfate. After the magnesium sulfate was filtered off, solvent was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography. Hexane-ethyl acetate (10:1) was used as an eluent and 5.9 g of the object compound was obtained as a pale yellow crystal.1H-NMR(CDCl3)deltappm: 1.07(6H, d, J=6.76Hz), 2.11?2.25(1H, m), 3.94(2H, d, J=6.43Hz), 7.15 (1H, d, J=8.91Hz), 7.81(1H, dd, J=8.91, 2.15Hz), 8.14(1H, d, J=2.15Hz)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 939-80-0, its application will become more common.

Reference:
Patent; Fuji Yakuhin Co., Ltd.; EP1471065; (2004); A1;,
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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. 4210-32-6, name is 4-(tert-Butyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H13N

Step 2: Preparation of 3-(4-(tert-butyl)-phenyl)-6-methoxyisoquinolin-1(2H)-one To a stirred solution of N,N-diethyl-4-methoxy-2-methylbenzamide (1 g, 4.52 mmol) in THF (10 ml) was added n-BuLi (2.82 ml, 4.52 mmol, in hexane) at -78¡ã C. and stirred for 1 h. Then to this 4-(tert-butyl)benzonitrile (0.72 g, 4.52 mmol) was added at same temperature and allowed to warm to room temperature and continued the stirring for another 1 h at room temperature. The reaction mixture was quenched with saturated NH4Cl solution and extracted with EtOac (2*100 ml). The organic phase was washed with brine, dried on Na2SO4, and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography (20percent ethyl acetate in pet ether) to get desired compound (0.72 g, 46.7percent) as a solid. 1H NMR (400 MHz, DMSO-d6): delta ppm 11.26(s, 1H), 8.11-8.09 (d, J=8 Hz, 1H), 7.73-7.71 (d, J=8 Hz, 2H), 7.52-7.50 (d, J=8 Hz, 2H), 7.06 (s, 1H), 7.05-7.03 (d, J=8 Hz, 1H), 6.82 (s, 1H), 3.89 (s, 3H), 1.32 (s, 9H); MS: MS m/z 308.2 (M++1).

According to the analysis of related databases, 4210-32-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; Hiebert, Sheldon; Rajamani, Ramkumar; Sun, Li-Qiang; Mull, Eric; Gillis, Eric P.; Bowsher, Michael S.; Zhao, Qian; Meanwell, Nicholas A.; Renduchintala, Kishore V.; Sarkunam, Kandhasamy; Nagalakshmi, Pulicharla; Babu, P. V. K. Suresh; Scola, Paul Michael; US2013/115190; (2013); A1;,
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Reference of 21803-75-8, 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 21803-75-8 as follows.

To a solution of phosgene (2.3 mL, 20% in toluene) in dry DCM (20 mL) was added a solution of 2-chloro-4-cyanoaniline (367 mg) and DIEA (372 mg) in dry DCM slowly. The resulting mixture was stirred at room temperature for 1 hr prior to evaporation to dryness. The residue was dissolved in DCM (10 mL) to which a solution of compound 1f (Example 1,510 mg) and DIEA (310 mg) in DCM was added. The resulting mixture was stirred overnight at room temperature. Aqueous sodium bicarbonate was added and the mixture was extracted with DCM. The organic phase was dried over MgS04 and evaporated to dryness.

According to the analysis of related databases, 21803-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SB PHARMCO PUERTO RICO INC; NEUROCRINE BIOSCIENCES INC; WO2005/63749; (2005); A1;,
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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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-(3-Nitrophenyl)acetonitrile

To a suspension of sodium hydride (617 mg, 14.16 mmol) in dimethylformamide (16 mL) under 10C, a solution of 3-nitrophenylacetonitrile (1.15 g, 7.09 mmol) and 2-(2-bromoethoxy)tetrahydro-2H-pyran (3.24 g, 15.5 mmol) in dimethylformamide (5 mL) was added, and the mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtrated, and then the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography. To the resulting oil was added methanol (15 mL) followed by p-toluenesulfonic acid mono-hydrate (90.7 mg), and then the mixture was stirred for three and half hours at room temperature. Water was added to the reaction mixture, the mixture was concentrated in vacuo. Then, saturated aqueous ammonium chloride was added thereto, and the mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtrated, and then the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography to give 740 mg of the title compound as a yellow solid. High-performance liquid chromatography/mass spectrometry m/z 251 (M+H) Retention time: 2.09 min.

The synthetic route of 621-50-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Dainippon Sumitomo Pharma Co., Ltd.; EP1679069; (2006); A1;,
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