Month: June 2021

Synthetic Route 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.

To a solution of 4-cyano-2-nitrotoluene (4.0 g, 24.8 mmol) insulfolane (10 mL) was added terephthaldehyde (1.66 g, 12.4 mmol)and piperidine (1.0 g, 12.6 mmol). The resulting mixturewas heatedat 150 C for 45 min, forming an orange precipitate. The reactionwas cooled to 25 C, and diluted with CHCl3 (20 mL). The mixturewas stirred for 30 min at 25 C, then the precipitatewas filtered andrinsed with additional CHCl3 (12 mL). The resulting solids weredried to yield compound 6 (4.1 g) as an orange powder. The orangepowder was added in triethyl phosphite (50 mL). The mixture washeated to reflux for 2 days and then cooled to 25 C, anddichloromethane (50 mL) was added. The suspension was stirredfor 30 min at 25 C, then the solids were filtered and rinsed withadditional CH2Cl2 (20 mL). The resulting solids were dried to yieldcompound 7 (2.1 g, 64%) as gold-yellow powder; 1H NMR (400 Hz,DMSO-d6): d 12.21 (s, 2H), 8.07 (s, 4H), 7.86 (s, 2H), 7.73 (d,J 8.0 Hz, 2H), 7.35 (d, J 8.0 Hz, 2H), 7.19 (s, 2H).

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:
Article; Liu, Yonghua; Hu, Xinxin; Wu, Yanbin; Zhang, Weixing; Chen, Xiaofang; You, Xuefu; Hu, Laixing; European Journal of Medicinal Chemistry; vol. 150; (2018); p. 771 – 782;,
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Related Products of 332-25-2, The chemical industry reduces the impact on the environment during synthesis 332-25-2, name is 4-(Trifluoromethoxy)benzonitrile, I believe this compound will play a more active role in future production and life.

Step 5 N-Hydroxy-4-(trifluoromethoxy)benzimidamide [0365] To a solution of 4-(trifluoromethoxy)benzonitrile (2.0 g, 10.6 mmol) in EtOH (20 mL), TEA (53 g, 53.0 mmol) and NH2OH.HCl (3.6 g, 26.5 mmol) were added in sequence. The mixture was refluxed for 4 h, cooled to RT, and concentrated under reduced pressure. The residue was diluted with H2O (20 mL), and extracted with EtOAc (20 mL×3). The combined organic layers were washed with H2O (1×10 mL) and brine (1×10 mL), dried over Na2SO4, filtered and concentrated to afford the crude N-hydroxy-4-(trifluoromethoxy)benzimidamide (2.0 g, 85percent), which was directly used for next reaction without further purification. MS (ES+) C8H7F3N2O2 requires: 220. found: 221 [M+H]+.

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, 4-(Trifluoromethoxy)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Institute For Applied Cancer Science/The University of Texas MD Anderson Cancer Center; Jones, Philip; DiFrancesco, Maria Emilia; Petrocchi, Alessia; Marszalek, Joe; Liu, Gang; US2014/57914; (2014); A1;,
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Related Products of 154607-01-9, A common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, molecular formula is C7H3BrClN, 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.

To a 50 mL round bottom flask was added BH3-THF (1.0 M in THF, 32.5 mL, 32.5 mmol) and 4-bromo-2-chlorobenzonitrile (1.76 g, 8.13 mmol) in THF (10 mL). The mixture was heated to reflux for 2 hours. The reaction mixture was quenched by the addition of an aqueous HCl solution (10 wt % yield). The pH was adjusted to 8 by adding an aqueous solution of NaOH (5 wt % yield) and extracted with dichloromethane. The organic layer was dried, filtered and concentrated to afford (4-bromo-2-chloro-phenyl)methanamine (1.62 g, 90% yield), which was used in the next step without further purification. LCMS (ESI) [M+H]+=220.0

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; Genentech, Inc.; Chan, Bryan; Drobnick, Joy; Gazzard, Lewis; Heffron, Timothy; Liang, Jun; Malhotra, Sushant; Mendonca, Rohan; Rajapaksa, Naomi; Stivala, Craig; Tellis, John; Wang, Weiru; Wei, BinQing; Zhou, Aihe; Cartwright, Matthew W.; Lainchbury, Michael; Gancia, Emanuela; Seward, Eileen; Madin, Andrew; Favor, David; Fong, Kin Chiu; Hu, Yonghan; Good, Andrew; US2018/282282; (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. 628-20-6, name is 4-Chlorobutyronitrile, A new synthetic method of this compound is introduced below., COA of Formula: C4H6ClN

A solution of 2- (1-methyl-1H-pyrazol-4-yl) -7- (piperidin-4-yl) -5 – ((2- (trimethylsilyl) ethoxy) -5H-pyrrolo [2,3-b] pyrazine (130 mg, 0.31 mmol)Of acetonitrile (8 mL)Potassium carbonate (110 mg, 0.79 mmol) was added sequentially to the solution,Potassium iodide (10 mg, 0.06 mmol) and4-chlorobutyronitrile (0.05 mL, 0.5 mmol)The reaction was heated at 50 C for 24 hours,Diluted with water (20 mL), extracted with dichloromethane (20 mL x 3), dried over anhydrous sodium sulfate and concentrated column chromatography (dichloromethane / methanol (v / v) = 8/1)120 mg of a yellow oil was obtained in a yield of 79.40%.

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; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Huang Jiuzhong; Zheng Changchun; Zhang Yingjun; Ouyang Luo; Mao Hongfen; Nie Biao; Xu Juan; Chen Hongfen; (137 pag.)CN106336413; (2017); A;,
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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 39581-21-0 as follows. Recommanded Product: N-Butyl-2-cyano-acetamide

General procedure: A mixture ofan aromatic aldehyde 1a-1f (1 mmol) with N-butyl-2-cyanoacetamide 2 (1 mmol) in ethanol (5 mL) wasrefluxed for 2 h, after which phthalhydrazide 3(1 mmol) was added to the mixture and refluxingcontinued for 3 h more. Upon completion of theprocess, according to TLC, the mixture was cooled toroom temperature and the precipitate was filtered off.The crude product was crystallized from ethanol togive the respective compound 4a-4f.

According to the analysis of related databases, 39581-21-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Elmi-Mehr; Davoodnia; Pordel; Russian Journal of General Chemistry; vol. 88; 12; (2018); p. 2595 – 2600;,
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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. 170572-49-3, name is 3-Fluoro-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H6FN

To a heterogenous solution of 3-fluoro-4-methyl-benzonitrile (5 g, 37.0 mmol) in ethanol (125 mL) at 25C was added hydroxylamine hydrochloride (5.14 g, 74 mmol) and triethylamine (10.3 mL, 74 mmol). The reaction mixture was heated at 80C for 1 hour. After cooling to room temperature volatiles were removed under reduced pressure thus affording a white gum that was used in the next step without any purification. LC/MS (Method A) retention time = 0.25 minutes, 169.3 (M+H). (0416) NMR (400 MHz, DMSO-de) delta ppm: 7.44 (t, 2H), 7.32 (d, 1 H), 5.85 (brs, 2H), 4.50 (brs, 1 H) 2.24 (s, 3H). (0417) 9F NMR (400 MHz, DMSO-de) delta ppm: -1 14.46 (s).

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 170572-49-3.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; HOFFMAN, Thomas, James; STIERLI, Daniel; BEAUDEGNIES, Renaud; POULIOT, Martin; HAAS, Ulrich, Johannes; (111 pag.)WO2018/219773; (2018); A1;,
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These common heterocyclic compound, 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, 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. Application In Synthesis of 5-Amino-2-fluorobenzonitrile

carboxylate as an off-white powder (382 mg). Methyl 3-chloro-1-methyl-4-[[1- (trifluoromethyl)cyclobutyl] sulfamoyl]pyrrole-2-carboxylate (150 mg, 0.4 mmol) and 5-amino- 2-fluorobenzonitrile (0.52 mmol) were dissolved in dry THF and cooled to 0C. Lithiumbis(trimethylsilyl)amide (1.24 mL, 1 M in THF, 1.24 mmol) was added dropwise and the reaction mixture was allowed to reach room temperature. After 1 hour lithium bis(trimethylsilyl)amide (0.5 mL, 1 M in THF, 0.5 mmol) was added and the reaction mixture was stirred for another hour. The volatiles were removed under reduced pressure and the residue was purified on silica gel using a heptane to EtOAc gradient. The collected fractions were evaporated todryness and the residue was crystallized from a heptane/EtOAc mixture yielding compound 221(91 mg) as off-white powder. Method D: Rt: 1.95mm mlz: 477.1 (M-H) Exact mass: 478.0. ?HNMR (400 MHz, DMSO-d6) oe ppm 1.75 – 1.88 (m, 2 H), 2.25 – 2.37 (m, 2 H), 2.41 – 2.48 (m, 2H), 3.79 (s, 3 H), 7.56 (t, J=9.1 Hz, 1 H), 7.68 (s, 1 H), 7.99 (ddd, J=9.2, 4.8, 2.6 Hz, 1 H), 8.20(dd, J=5.7, 2.6 Hz, 1 H), 8.61 (s, 1 H), 10.67 (s, 1 H).

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

Reference:
Patent; JANSSEN R&D IRELAND; VANDYCK, Koen; HACHE, Geerwin, Yvonne, Paul; LAST, Stefaan, Julien; MC GOWAN, David, Craig; ROMBOUTS, Geert; VERSCHUEREN, Wim, Gaston; RABOISSON, Pierre, Jean-Marie, Bernard; WO2014/184350; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 57381-49-4, name is 2-Bromo-4-chlorobenzonitrile, 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 57381-49-4, Quality Control of 2-Bromo-4-chlorobenzonitrile

Borane tetrahydrofuran complex (55 mL, 1.0 M in THF) were provided with ice cooling, then slowly a solution of 2-bromo-4-chlorobenzonitrile (4.00 g, 18.5 mmol) in THF (10 mL) was added. Thereafter the reaction-mixture was heated under reflux for 16 hours. The reaction was quenched by addition of methanol. 20 mL of hydrochloric acid (1.0 N) were added dropwise with ice cooling. The solution was rendered alkaline with 1.0 M sodium hydroxide solution and extracted with dichloromethane. The organic phase was dried over sodium sulfate and evaporated to yield 2.10 g (36%) of the title compound as the off-white solid. The reaction was monitored by TLC (ethyl acetate/petroleum ether=1 :1, Rf = 0.3). MS (ESIpos): m/z = 220 [M+H]+.

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; BAYER PHARMA AKTIENGESELLSCHAFT; WORTMANN, Lars; SAUTIER, Brice; EIS, Knut; BRIEM, Hans; BOeHNKE, Niels; VON NUSSBAUM, Franz; HILLIG, Roman; BADER, Benjamin; SCHROeDER, Jens; PETERSEN, Kirstin; LIENAU, Philip; WENGNER, Antje, Margret; MOOSMAYER, Dieter; WANG, Qiuwen; SCHICK, Hans; (510 pag.)WO2018/172250; (2018); A1;,
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Application of 69395-13-7, 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. 69395-13-7 name is 4-(2-Hydroxyethyl)benzonitrile, 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.

To a solution of 4-(2-hydroxyethyl)benzonitrile (10.0 g, 67.94 mmol) in CH2Cl2 (175 mL) at 0 C. was added Et3N (11.36 mL, 8.25 mmol) and MsCl (6.31 mL, 81.53 mmol). After stirring at 0 C. for 3.5 hours, the reaction was poured into water (100 ml) and separated. Organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Crude residue was dissolved in DMF (100 mL) and NaN3 (9.15g, 140.72 mmol) and water (5 mL) were added. The resulting solution was heated to 125 C. After overnight stirring at 125 C., the crude reaction mixture was cooled, diluted with EtOAc (200 mL) and poured into water (150 mL). Organic layer was washed with water (5×150 mL), dried over sodium sulfate, filtered, and concentrated to give 4-(2-azidoethyl)benzonitrile which was used without purification

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(2-Hydroxyethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Su, Dai-Shi; Bock, Mark G.; US2005/20591; (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. 1885-38-7, name is (E)-Cinnamonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of (E)-Cinnamonitrile

General procedure: Under a nitrogen atmosphere, a mixture of [RhCl(C2H4)2]2 (1.8 mg,0.0045 mmol) and ligand L1f (3.7 mg, 0.0099 mmol) in toluene(1 mL) was stirred at r.t. for 15 min, at which time arylboronic acid(0.60 mmol) was added, followed by cyanoalkenes (0.30 mmol),aqueous KOH (0.75 M in H2O, 0.20 mL, 0.15 mmol) and toluene(1 mL). The reaction was stirred at 80 C for 12 h, after which thereaction mixture was concentrated in vacuo and purified by silica gelflash column chromatography (petroleum ether/ethyl acetate as eluent)to give the product

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 1885-38-7.

Reference:
Article; Xue, Feng; Zhu, Yong; Qi, Xiaolei; Journal of Chemical Research; vol. 42; 6; (2018); p. 300 – 304;,
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