Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 179898-34-1, name is 3-Bromo-5-fluorobenzonitrile, 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 179898-34-1, Recommanded Product: 3-Bromo-5-fluorobenzonitrile

A solution of 3-bromo-5-fluorobenzonitrile (CVII) (44.0 g, 220.0 mmol, 1.0 eq) was dissolved in THF (30 mL). BH3-Me2S (33.43 g, 440.0 mmol, 2.0 eq) was added to the solution at 20 C. Then it was stirred at 80 C. for 2 h, HCl (6 N, 100 mL) was added to the mixture slowly at 20 C. The mixture was stirred at 80 C. for 1 h, then it was washed with EtOAc (300 ml). The water phase was basified with 50% aqueous NaOH and it was extracted with EtOAc (300 mL¡Á3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to produce (3-bromo-5-fluoro-phenyl)methanamine (CVIII) (24.0 g, 117.62 mmol, 53.5% yield). 1H NMR (CDCl3, 300 MHz) 3.86 (s, 2H), 7.01 (d, J=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 7.28 (s, 1H); ESIMS found C7H7BrFN m/z 203.9 (Br79M+H).

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Reference:
Patent; Samumed, LLC; KC, Sunil Kumar; Wallace, David Mark; Cao, Jianguo; Chiruta, Chandramouli; Hood, John; (268 pag.)US2016/68529; (2016); A1;,
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These common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, 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. Formula: C11H13NO3

Following procedures similar to that of Step D but substituting 3,4,5-trimethoxyphenylacetonitrile for 3-methoxy-5-(methylthio)-4-propoxyphenylacetonitrile, there was prepared ethyl 3,4,5,-trimethoxy-alpha-cyanobenzeneacetate in 89% yield as a clear oil. NMR (CDCl3): delta 1.35 (t, 3H, -CO2CH2C H 3), 4.25 (q, 2H, -CO2C H 2CH3), 4.65 (s, 1H, -C H (CN)CO2Et), 6.05 (s, 2H, Ar-H).

The synthetic route of 3,4,5-Trimethoxyphenylacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; EP257921; (1988); A2;,
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Synthetic Route of 185836-35-5, 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 185836-35-5 as follows.

A mixture of 0.93 g of lithium aluminum hydride and 30 ml ofTHF was stirred under cooling on ice. Thereafter, a mixture solution of 2.8 g of 4-benzyloxy-2-fluorobenzonitrile and 10 ml of THF was added dropwise to the reaction mixture. The obtained mixture was stirred at a room temperature for 6 hours. Thereafter, the reaction mixture solution was cooled to 0C. 0.9 ml of water, 0.9 ml of a 15% sodium hydroxide aqueous solution, and 2.7 ml of water were successively added to the reaction mixture, and the obtained mixture was stirred at a room temperature for 1 hour. Thereafter, the reaction mixture was filtrated through Celite (registered trade mark), and it was then concentrated under reduced pressure, so as to obtain 2.5 g of 4-benzyloxy-2-fluorobenzylamine.4-benzyloxy-2-fluorobenzylamine [Show Image] 1H-NMR (CDCl3) delta: 3.82 (2H, s), 5.04 (2H, s), 6.67-6.75 (2H, m), 7.18-7.24 (1H, m), 7.32-7.45 (5H, m).

According to the analysis of related databases, 185836-35-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP2248423; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, 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 328-87-0, category: nitriles-buliding-blocks

EXAMPLE 1 Preparation of 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-4-nitro phenyl ether A solution of potassium hydroxide (3.2 g. 0.05 mole of 89.3% purity) and p-nitrophenol (7.0 g. 0.05 mole) in methanol (25 ml.) is stripped under reduced pressure. The residue is dissolved in sulfolane, 4-chloro-3-cyano alpha,alpha,alpha-trifluorotoluene (10.3 g. 0.05 mole) added, and the resulting solution heated at 150 C. for 5 hours. After cooling, the solution is diluted with benzene (350 ml.) washed with water (6*250 ml.), dried, and the solvent removed. The residue (12.5 g.) is recrystallized from isopropanol to give 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-4-nitrophenyl ether (7.6 g., 49%) m.p. 93-98 C.

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-Chloro-5-trifluoromethylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Rohm and Haas Company; US30361; (1980); E1;,
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Some common heterocyclic compound, 22972-63-0, name is 2-(3,5-Dimethoxyphenyl)-2-methylpropanenitrile, molecular formula is C12H15NO2, 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. Formula: C12H15NO2

PREPARATION E 2-Methyl-2-(3,5-dihydroxyphenyl)-5-phenylpentane To a solution of the Grignard reagent prepared from 2-phenylbromoethane (5.5 g.), magnesium (0.8 g.) and dry ether (60 ml.) is added a solution of 2-methyl-2-(3,5-dimethoxyphenyl)propionitrile (2.75 g.) in dry ether (20 ml.). The ether is distilled off and replaced by dry benzene (50 ml.) and the mixture refluxed for 48 hours. It is then decomposed by careful treatment with dilute sulfuric acid and heated on a steam bath for 1 hour. The mixture is then extracted with ether, the extract dried (MgSO4) and concentrated to an oil. Distillation of the oil in vacuo affords 2-methyl-2-(3,5-dimethoxyphenyl)-5-phenyl-3-pentanone; b.p. 168 C./0.2 mm. (Yield: 2.32 g., 60%)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22972-63-0, its application will become more common.

Reference:
Patent; Pfizer Inc.; US4143139; (1979); A;,
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Reference of 846023-24-3, These common heterocyclic compound, 846023-24-3, name is 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide, 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.

EXAMPLE 49 2E/Z)-2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-methoxy-3-{5-[(4-methylpiperazin-1-yl)methyl]-3-furyl}phenyl)amino]acrylamide To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (261 mg, 1.01 mmol) in 5 mL of iso-propanol was added triethylorthoformate (0.504 mL, 3.03 mmol). The mixture was heated to reflux and (4-methoxy-3-{5-[(4-methylpiperazin-1-yl)methyl]-3-furyl}phenyl)amine (320 mg, 1.06 mmol) in 9 mL of iso-propanol was added dropwise. This mixture was heated at reflux for 25 hours. The mixture was allowed to cool to room temperature and the solid was collected by filtration, washed with iso-propanol, to provide 465 mg (81%) of (2E/Z)-2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-methoxy-3-{5-[(4-methylpiperazin-1-yl)methyl]-3-furyl}phenyl)amino]acrylamide as a gray solid, mp 198-199 C.; MS 570.1 (M+H)+. Analysis for C28H29Cl2N5O4-0.2 H2O: Calcd: C, 58.58; H, 5.16; N, 12.20. Found: C, 58.50; H, 5.07; N, 12.07.

Statistics shows that 2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide is playing an increasingly important role. we look forward to future research findings about 846023-24-3.

Reference:
Patent; Wyeth Holdings Corporation; US2005/43537; (2005); A1;,
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Application of 845866-92-4, 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. 845866-92-4, name is 6-Amino-3-bromo-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step A: 2-amino-5-bromo-6-fluoro-3-nitro-benzonitrileTo a cooled (0 C) solution of 6-amino-3-bromo-2-fluoro-benzonitrile (8.0 g, 37 mmol) in acetonitrile (40 mL) under nitrogen was added dropwise a solution of nitronium tetrafluoroborate in acetonitrile. The reaction mixture and stirred for 16 h at RT. The reaction mixture was treated with brine and extracted with ethyl acetate. The organic fraction was washed with water followed by brine and dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography (10 to 20% ethyl acetate:hexanes) afforded 5.0 g (52%) of the title compound. 1 H NMR (300 MHz, CDCI3): delta 8.6 (d, J= 6.9 Hz, 1 H), 6.8 – 7.1 (br. s, 2H).

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, 6-Amino-3-bromo-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; OSI PHARMACEUTICALS, LLC; HOMBERGER, Keith, R.; BERGER, Dan, M.; CHEN, Xin; CREW, Andrew, P.; DONG, Hanqing; KLEINBERG, Andrew; LI, An-Hu; MA, Lifu; MULVIHILL, Mark, J.; PANICKER, Bijoy; SIU, Kam, W.; STEINIG, Arno, G.; TARRANT, James, G.; WANG, Jing; WENG, Qinghua; SANGEM, Rajaram; GUPTA, Ramesh, C.; WO2011/100502; (2011); 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. 1141894-75-8, name is 4-(Aminomethyl)-3-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 4-(Aminomethyl)-3-(trifluoromethyl)benzonitrile

Example 74; (cis)-N-{[4-cyano-2-(trifluoromethyl)phenyl]methyl}-3-{[4-methyl-6-(methylamino)-1 ,3,5- triazin-2-yl]amino}cyclohexanecarboxamide; To a solution of 3-{[4-methyl-6-(methylamino)-1 ,3,5-triazin-2- yl]amino}cyclohexanecarboxylic acid (0.100 g, 0.264 mmol) in N,N-Dimethylformamide (DMF) (4 ml) was added 4-(aminomethyl)-3-(trifluoromethyl)benzonitrile (0.053 g, 0.264 mmol) followed by diisopropylethylamine (0.101 ml, 0.580 mmol) and 1 H-1 ,2,3- benzotriazol-1-yloxy-tris(dirnethylamino)-phosphonium hexafluorophosphate (BOP reagent, 0.128 g, 0.290 mmol). The reaction was stirred at room temperature for 4 hours and then purified by preparative HPLC to provide (cis)-N-{[4-cyano-2- (trifluoromethyl)phenyl]methyl}-3-{[4-methyl-6-(methylamino)-1 ,3,5-triazin-2- yl]amino}cyclohexanecarboxamide (83 mg, 0.148 mmol, 56 %). MS (ES) m/e 448[M+H]+. 1H NMR (400 MHz, DMSO-D6) D 7.8 (bs, 1 H), 7.3 (bs, 1 H), 7.2 (m, 1 H), 6.9 (m, 1 H), 3.8 (bs, 2H), 3.3 (bm, 1 H), 2.2 (bm, 4H), 1.8 – 1.5 (bm, 4H), 1.3 – 1.1 (bm, 4H), 0.8 – 0.5 (bm, 4H)

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; SMITHKLINE BEECHAM CORPORATION; WO2009/49157; (2009); A1;,
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Reference of 1813-33-8, A common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, molecular formula is C8H3ClF3N, 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.

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate boronic acid (1.20 mmol)were dissolved in toluene/dioxane:2 N Na2CO3 (2:1:1) solution(6 ml). Tetrakis(triphenyl-phosphine)palladium(0) (0.10 mmol)and 1,10-Ferrocenediyl-bis(diphenylphosphine) (0.20 mmol) wasadded to the mixture and it was refluxed for 12 h. After cooleddown to ambient temperature, the reaction was filtered over celiteand extracted with EtOAc twice. The combined organic extractswere dried over MgSO4, filtered, and concentrated in vacuo. Theresidue was purified by flash column chromatography on silicagel using EtOAc/hexanes (1:10) eluant condition. (R-B(OH)2 =1-pentenyl boronic acid for 53, 1-cyclohexenylboronicacid for 54).

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; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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These common heterocyclic compound, 950596-58-4, name is 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, 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. Recommanded Product: 950596-58-4

General procedure: A mixture of 3 (2.00mmol), toluene (5mL), and DMF-DMA (4.00mmol) were heated up to 35-40C and acetic acid (0.10mL) was added. After 15min, the resultant mixture was cooled to approximately 25C. The solvent was completely evaporated. The residue was added to water and basified pH to 13 by the addition of 20% sodium hydroxide. The obtained mixture was extracted with methylene chloride (2¡Á15mL) and the combined organic extracts were washed with water (2¡Á20mL) and brine (1¡Á70mL), then dried over anhydrous MgSO4. The organic solvent was evaporated to give 4 as oil (Yield 61-94%).

The synthetic route of 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Li; Zhang, Yaling; Liu, Juan; Wang, Weijia; Li, Xiabing; Zhao, Lijun; Wang, Wei; Li, Baolin; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 689 – 697;,
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