Tag: M.W=100-200

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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 4-Cyano-3-trifluoromethylaniline

A solution of 2-(2-methoxyethyl)-1 -oxo-3-(thiophen-2-yl)-1 ,2,3,4-tetrahydroisoquinoline-4- carboxylic acid (100 mg, 0.30 mmol) and thionyl chloride (1.5 mL) in chloroform (1 .5 mL) was refluxed for 1 hour. After cooling, the volatiles were removed under reduced pressure. The residue was dissolved in chloroform (1 .5 mL) under nitrogen atmosphere and triethylamine (100 muL) was added. To this solution was added 4-amino-2- (trifluoromethyl)benzonitrile (67 mg, 0.36 mmol) and the stirring was continued at 5O0C for 5 days. The mixture was evaporated under reduced pressure and the crude material was purified by flash chromatography on silica gel using a gradient of ethyl acetate (15 – 70%) in heptane followed by precipitation from a mixture of dichloromethane/heptane afford 23.3 mg (15%) of the titled compound as a tan solid. ESI/APCI(+): 500 (M+H). ESI/APCI(- ): 498 (M-H). 1H NMR (DMSO-c/6) delta 10.38 (1 H, s, NH), 8.31 (1 H, s), 8.14 (1 H, d), 8.04 (1 H, d), 7.94 (1 H, d), 7.52-7.42 (2H, m), 7.37 (1 H, d), 7.32 (1 H, d), 7.02 (1 H, s), 6.93 (1 H, t), 5.62 (1 H, s), 4.39 (1 H, s), 4.14 (1 H, dt), 3.40 (2H, t), 3.08 (1 H, dt), 2.91 (3H, s).

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN, K.U.LEUVEN R&D; BARDIOT, Dorothee; BLANCHE, Emilie; CHALTIN, Patrick; KOUKNI, Mohamed; LEYSSEN, Pieter; NEYTS, Johan; MARCHAND, Arnaud; VLIEGEN, Inge; WO2010/55164; (2010); A2;,
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Electric Literature of 939-79-7, A common heterocyclic compound, 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, molecular formula is C8H6N2O2, 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 mixture of 0.32 g of 3-nitro-4-methyl-benzonitrile (1; 0.32 g, 2.0 mmol), 3-fluoro-4-bromo-benzaldehyde (35; 0.40 g, 2.0mmol), piperidine (0.1 mL, 1.0 mmol) and sulfolane (3 g) was heated in a sealed tube at 150-160 C for 1 h. After cooling to room temperature, water (10 mL) was added. The resulting precipitate was filtered and dried under high vacuum to provide 0.64 g (94%) of product as yellow 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:
Article; Nguyen, Son T.; Williams, John D.; Butler, Michelle M.; Ding, Xiaoyuan; Mills, Debra M.; Tashjian, Tommy F.; Panchal, Rekha G.; Weir, Susan K.; Moon, Chaeho; Kim, Hwa-Ok; Marsden, Jeremiah A.; Peet, Norton P.; Bowlin, Terry L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3366 – 3372;,
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Synthetic Route of 3441-01-8, 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 3441-01-8 as follows.

To a stirred solution of 2-((6-bromopyridin-3-yl)(methoxy)methyl)-6- (trifluoromethyl)-3H-imidazo[4,5-b]pyridine (200 mg, 0.517 mmol) in THF (5 mL) were added 3-cyanobenzamide (113 mg, 0.775 mmol) and sodium 2-methylpropan-2-olate (99 mg, 1.0 mmol), Brettphos Pd G3 (47 mg, 0.052 mmol) at RT. After the addition was finished, the reaction was stirred at 60 °C for 16 h. The reaction was diluted with water, extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04i filtered and concentrated in vacuo to afford a residue, which was purified by reversed phase HPLC, eluting with water (0.1 percentTFA)-ACN to afford the title compound as a TF A salt (Ex. 39). XH NMR (400 MHz, CD3OD) delta 8.67 (s, 1 H), 8.52 (d, J=1.8 Hz, 1 H), 8.32 (t, J=1.4 Hz, 1 H), 8.28 – 8.24 (m, 3 H), 7.96-7.94 (m, 2 H), 7.74-7.72 (m, 1 H),5.77(s, 1 H), 3.54 (s, 3 H); MS (EI) m/z: 453 [M+H]+.

According to the analysis of related databases, 3441-01-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ZHOU, Hua; FRADERA, Xavier; HAN, Yongxin; MCGOWAN, Meredeth, A.; SCIAMMETTA, Nunzio; WHITE, Catherine; YU, Wensheng; (89 pag.)WO2019/27856; (2019); A1;,
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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 16588-02-6 as follows. Formula: C7H3ClN2O2

2-(Benzylthio)-5-nitrobenzonitrile[0294] To a solution of 2-chloro-5-nitrobenzonitrile (27.375 g, 0.15 mol) in MeCN (500 ml) was added K2C03 (24.84 g, 0.18 mol) and phenylmethanethiol (17.71 ml, 0.15 mol). The solution was stirred at room temperature for overnight. The mixture was filtered through the celite pad and the filtrate was concentrated in vacuo to give 2-(benzylthio)-5-nitrobenzonitrile (40.5 g, 100%) as a yellow solid. 1H NMR: CDC13400 MHz 58.43 (s, 1H), 8.27-8.25 (m, 1H), 7.44-7.31 (m, 6H), 4.35 (s, 2H).

According to the analysis of related databases, 16588-02-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ANACOR PHARMACEUTICALS, INC.; HERNANDEZ, Vincent, S.; LI, Xianfeng; ZHANG, Suoming; AKAMA, Tsutomu; ZHANG, Yanchen; LIU, Yang; PLATTNER, Jacob, J.; ALLEY, Michael, Kevin Richard; ZHOU, Yasheen; NEIMAN, James, A.; WO2011/60196; (2011); A1;,
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Related Products of 25808-30-4,Some common heterocyclic compound, 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, molecular formula is C3H7ClN2, 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. N-Carbethoxy-N-methylaminoacetonitrile Triethylamine (5.2 ml; 37.6 mmoles) was added to a suspension of methylaminoacetonitrile hydrochloride (2.0 g; 18.8 mmoles) in 20 ml of methylene chloride. The resulting suspension was cooled in an ice-bath and a solution of ethyl chloroformate (2.14 g; 19.8 mmoles) in 10 ml of methylene chloride was added over a 0.5 hour period, and the mixture was then heated at reflux temperature for 18 hours. The reaction mixture was evaporated under reduced pressure to give a semi-solid residue which was triturated with diethyl ether and filtered, and the filtrate was evaporated under reduced pressure to yield the title compound as an oil (2.2 g), bp 96°-98°/5.2 mm Hg.

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

Reference:
Patent; Bristol-Myers Company; US4471122; (1984); A;; ; Patent; Bristol-Myers Company; US4510309; (1985); A;; ; Patent; Bristol-Myers Company; US4394508; (1983); A;,
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Synthetic Route of 123-06-8, 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. 123-06-8, name is Ethoxymethylenemalononitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 2-(ethoxymethylene)propanedinitrile (20 g, 163.80 mmol) was added hydrazine hydrate (15.9 mL, 327.60 mmol) dropwise at 0 C and the resultant reaction mixture was heated at 100 C in a closed reagent bottle for 1h. The reaction was monitored by TLC. After completion, the reaction mixture was cooled to RT and water (50 mL) was added. The product was extracted using EtOAc (3×200 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 15 g of 5- amino-1H-pyrazole-4-carbonitrile as a light brown solid.

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

Reference:
Patent; MEDIVATION TECHNOLOGIES, INC.; RAI, Roopa; CHAKRAVARTY, Sarvajit; GREEN, Michael, John; PHAM, Son, Minh; PUJALA, Brahmam; AGARWAL, Anil, Kumar; NAYAK, Ajan, Kumar; KHARE, Sweta; GUGULOTH, Rambabu; RANDIVE, Nitin, Atmaram; WO2015/69441; (2015); A1;,
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Electric Literature of 939-79-7, 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. 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Step A 2-Methyl-5-(4H-[1,2,4]triazol-3-yl)-phenylamine Hydrogen chloride was bubbled through a solution of 3-nitro-p-tolunitrile (0.49 g, 3 mmol) in 40 mL of EtOH at room temp for 10 min. The solution was stirred at room temp for 60 min, and the solvent was then evaporated under vacuum to dryness to give a white solid. The intermediate so obtained was dissolved in 20 mL of EtOH, neutralized with sodium ethoxide solution, and the resulting precipitate was removed by filtration. To the filtrate at rt. was added formic hydrazide (0.2 g, 3 mmol), stirring of the solution was then continued at room temp for 2 h, then the solvent was evaporated under vacuum. The residue was dissolved in 30 mL of m-xylene and refluxed at 150 C. for 16 h. The solvent was then evaporated under vacuum and the crude product was purified by flash chromatography to afford 0.26 g of nitro intermediate. (Yield: 43%). MS (m/z) calcd for C9H8N4O2 (MH+) 205.2, found, 205.1.

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

Reference:
Patent; Leftheris, Katerina; Wrobleski, Stephen T.; Dyckman, Alaric J.; US2005/43306; (2005); 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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 4-Cyano-3-trifluoromethylaniline

2-ethoxy-6-pentadecyl-benzoyl chloride was condensed with 4-Amino-2-trifluromethyl benzonitrile in dichloromethane in presence of triethylamine as acid scavenger to, yield N-(4-Cyano-3-trifluoromethyl-phenyl)-2-ethoxy-6-pentadecyl-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. m/z: 545.5 (M+1),359.6, 331.6, 213.3, 175.1, 149.1, 107.1,91,55.1

According to the analysis of related databases, 654-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kundu, Tapas Kumar; Balasubramanyam, Karanam; Swaminathan, Vankatesh; US2006/167107; (2006); 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. 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

General procedure: To a solution of 2a (1 equiv.) and amine (1.2 equiv.) in dichloromethane was added triethylamine (2 equiv.) as outlined in reaction Scheme 1. The reaction mixture was cooled to 0C and propylphosphonic acid anhydride (T3P) (2.5 equiv.) was added. The reaction mixture was then warmed to room temperature and stirred for 16 h. After the completion of reaction, the reaction mixture was diluted with dichloromethane and washed successively with saturated sodium bicarbonate solution, water, brine and dried over anhydrous Na2S04. The solvent was then removed under reduced pressure to yield the crude product, which was purified over silica gel using 30%-60% ethyl acetate in pet-ether as eluant to yield the pure IIj in 35 to 40% yields.

The synthetic route of 53312-81-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ST. JUDE CHILDREN’S RESEARCH HOSPITAL; MMV MEDICINES FOR MALARIA VENTURE; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; GUY, Rodney Kiplin; ZHU, Fangyi; CLARK, Julie Anne; GUIGUEMDE, Wendyam Armand; FLOYD, David; KNAPP, Spencer; STEIN, Philip; CASTRO, Steve; WO2013/27196; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, 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 115279-57-7, Safety of 2-(4-Aminophenyl)-2-methylpropanenitrile

Step 1. 2-[4-(4,5-dichloro-2-nitroanilino)phenyl]-2-methylpropanenitrile The title compound was prepared according to the procedure described in step 3 of Example 1 from 2,4,5-trichloronitroaniline and 2-(4-aminophenyl)-2-methylpropanenitrile (Axton, C. A.; et al. J.Chem.Soc.Perkin Trans.], 1992, 17, 2203). 1H-NMR (CDCl3) delta9.38 (1H, br), 8.31 (1H, s), 7.54 (2H, d, J=8.58 Hz), 7.30-7.22 (3H, m), 1.75 (6H, s).

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:
Patent; Audoly, Laurent; Okumura, Takako; Shimojo, Masato; US2002/77329; (2002); A1;,
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