Month: November 2020

42872-74-2, 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 42872-74-2 as follows.

Intermediate 28a) A solution of 3-bromo-4-methylbenzonitrile (1 g), acetamidine hydrochloride (714 mg), cesium carbonate (5 g) and copper (I) bromide (36 mg) in dry dimethyl sulfoxide (25 mL) was stirred at 120 C for 3 h. The mixture was chilled, diluted with EtOAc (200 mL) and washed with water. The organic layer was dried and the volatiles were removed under reduced pressure. The residue was purified by chromatography (Si02, 150 g, DCM/ MeOH) to yield the desired product (36% yield). LC-MS (Method 1): m/z [M+H]+ = 252.1 (MW calc. = 252.11 ); R, = 3.5 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 42872-74-2, and friends who are interested can also refer to it.

Reference:
Patent; GRUeNENTHAL GMBH; NORDHOFF, Sonja; WACHTEN, Sebastien; KLESS, Achim; VOSS, Felix; RITTER, Stefanie; WO2014/108337; (2014); A1;,
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63069-50-1, Adding a certain compound to certain chemical reactions, such as: 63069-50-1, name is 4-Amino-3-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 63069-50-1.

Step 1 : To a stirred solution of 4-amino-3-fluorobenzonitrile (2.0 g, 14.7 mmol) and potassium thiocyanide (5.7 g, 59 mmol) in AcOH (50 mL) was added a solution of bromine (2.3 g, 14.7 mmol) in AcOH (5 mL) over 20 min. The mixture was stirred at rt for 20 h, poured into ice-water (100 mL). Ammonium hydroxide solution (28%) was added to pH 8, stirred for 2 h, filtered, washed with water and dried to afford 4-amino-3-fluorobenzonitrile lnt-6a-1

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; GILEAD SCIENCES, INC.; KINZEL, Olaf; KREMOSER, Claus; SCHMITT, Aaron C.; GEGE, Christian; (205 pag.)WO2016/96115; (2016); 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. 10406-25-4, name is 4-(Aminomethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., 10406-25-4

EXAMPLE 1 13.2 g of p-cyanobenzylamine was added dropwise to 200 ml of water and 15.8 g of potassium permanganate with vigorous stirring at room temperature over 20 minutes. The mixture was adjusted to pH 1 by sulfuric acid and stirred at room temperature for 5 hours. The p-cyanobenzaldehyde obtained had a yield of 26% (on a basis of cyanobenzylamine compound, hereafter the same) determined by the analysis of high performance liquid chromatography.

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; Showa Denko K.K.; US6262292; (2001); B1;,
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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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 127946-77-4

To a 100 mL two-neck flask were added 1-((tert-butylcarbonate)amino)cyclohexanecarboxylic acid (2.43 g, 10 mmol), 1-amino-1-cyclopropanecarbonitrile hydrochloride (1.42 g, 12 mmol) and DMF (15 mL). To the mixture were added HATU (5.32 g, 14 mmol) and ethyldiisopropylamine (8.8 mL, 50 mmol) at 0C under nitrogen protection. The mixture was stirred for 1.0 h at 0 C under nitrogen protection. To the reaction mixture was added saturated aqueous sodium chloride (30 mL), and the resulting mixture was extracted with ethyl acetate (30 mL*3). The combined organic layer was washed with saturated brine (30 mL*3), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give light yellow oil (2.82 g, 91%). This crude product was used in next step without further purification.

The synthetic route of 127946-77-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; WANG, Xiaojun; ZHOU, Pingjian; YANG, Chuanwen; HUANG, Changwei; XIONG, Shaohui; ZHANG, Yingjun; ZHANG, Jiancun; (139 pag.)EP3342765; (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. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., 874-89-5

a 2-Chlorobenzenesulfonic acid 3-[(4-cyanophenyl)methoxy]-5-methylphenyl ester Diethyl azodicarboxylate (524 mg, 3.0 mmol) was added to a solution of 2-chlorobenzenesulfonic acid 3-hydroxy-5-methylphenyl ester (900 mg, 3.0 mmol), as prepared in step (c) of the Example 1, 4-cyanobenzyl alcohol (400 mg, 3.0 mmol; Yoon et al., J. Org. Chem. 38:2786-2792 (1973)), and triphenylphosphine (790 mg, 3.0 mmol) in tetrahydrofuran (20 mL) at 0 C. The mixture was stirred at 0 C. for 2 h and at room temperature for 3 h. The reaction mixture was quenched with water (50 mL) and extracted with ethyl acetate (3*50 mL). The organic phase was washed sequentially with saturated NaHCO3 (2*50 mL) and brine (2*50 mL), and dried over Na2 SO4. The solvent was removed in vacuo and the residue was purified by flash column chromatography (2:1 ethyl acetate:hexane) to give the title compound as a white solid (0.95 g, 76%). 1 H-NMR (300 MHz, CDCl3) delta 2.26 (s, 3H), 5.03 (s, 2H), 6.57 (t, 1H, J=2.2 Hz), 6.59 (s, 1H), 6.67 (s, 1H), 7.38 (t, 1H, J=5.8 Hz), 7.49 (d, 2H, J=4.2 Hz), 7.60 (m, 2H), 7.67 (d, 2H, J=3.5 Hz) and 7.96 (d, 1H, J=3.6 Hz).

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; 3-Dimensional Pharmaceuticals, Inc.; US6034127; (2000); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding some certain compound to certain chemical reactions, such as: 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, 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 179897-89-3. 179897-89-3

a) 5-Bromo-2-(4-methyl-imidazol-1-yl)-benzonitrile A mixture of 5-bromo-2-fluoro-benzonitrile (25.0 g, 125 mmol), 4-methylimidazole (12.5 g, 152 mmol), potassium carbonate (34.55 g, 250 mmol) in DMSO (500 mL) was stirred at 90 C. for 16 h. Water (1.5 L) was added and the resulting suspension was stirred with ice-bath cooling for 1 h. The precipitate was filtered, washed with water (0.5 L) and dried at 50 C. over KOH. The resulting raw material (25.6 g) was dissolved in boiling Ethyl acetate (300 ml). After addition of diisopropylether (300 ml) the solution was allowed to cool to room temperature. Filtration and drying afforded the title compound (19.35 g, 59%) as a white solid. Mp 166 C.

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 5-Bromo-2-fluorobenzonitrile.

Reference:
Patent; Buettelmann, Bernd; Knust, Henner; Thomas, Andrew William; US2006/128691; (2006); A1;,
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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. 63069-50-1 name is 4-Amino-3-fluorobenzonitrile, 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. 63069-50-1

1.6.1. Step i): 2,4-Difluoro-6-iodoaniline Iodine (1 eq, 19.7 g) is dissolved in EtOH (350 mL) at room temperature, and 2,4-difluoroaniline (1 eq, 8 mL) and silver sulfate (1 eq, 24.1 g) are added. The suspension is stirred at room temperature overnight. After completion of the reaction as seen by LC-MS, the silver salts are filtered off and the filtrate is concentrated in vacuo. The residue is dissolved in DCM and washed with sat. Na2S203 (3 x 100 mL). The organic layer is washed with sat. brine, dried over anhydrous sodium sulfate, and purified by column chromatography (silica, petroleum ether/EtOAc; 100:0 to 95:5) to give the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; QUINTON, Evelyne; JOANNESSE, Caroline, Martine, Andree-Marie; DE BLIECK, Ann; BLANC, Javier; (263 pag.)WO2017/12647; (2017); A1;,
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Adding some certain compound to certain chemical reactions, such as: 1483-54-1, name is 2-Amino-4-(trifluoromethyl)benzonitrile, 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 1483-54-1. 1483-54-1

General procedure: Benzonitrile 1a (103 mg, 1.0 mmol) and WEPPA (2.0 mL) were added into a 10-mL closed tubewith a stir bar. Then the reaction was stirred in a closed vessel synthesis reactor at 150 C for 0.5 h.After cooling to ambient temperature, the resulting precipitate was collected by filtration, washed withice water, and further dried in a vacuum drying oven. The filtrate was evaporated under reducedpressure. The resultant residue was purified by silica gel column chromatography (eluent: petroleumether (35-60 C)/EtOAc = 2:1 to 0:1, v/v). Finally, these two parts were combined to produce the desiredbenzamide 2a with a 94% yield.

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 2-Amino-4-(trifluoromethyl)benzonitrile.

Reference:
Article; Sun, Yajun; Jin, Weiwei; Liu, Chenjiang; Molecules; vol. 24; 21; (2019);,
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6393-40-4, 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. 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 4.2. General procedure for the indium-mediated reductivecyclization of 2-nitroanilines to prepare quinoxalines A mixture of the 2-nitroaniline derivative (1.0 mmol), dione (1.0or 2.0 mmol), indium (0.574 g, 5.0 mmol), and acetic acid (0.300 g,5 mmol or 0.600 g,10 mmol) or indium chloride (0.221 g,1 mmol or0.265 g,1.2 mmol) in methanol (5 mL) or toluene (5 mL) was stirredat 50 C, 80 C, or reux under a nitrogen atmosphere. After com-pletion of the reaction, the reaction mixture was diluted with ethylacetate (30 mL), ltered through Celite, and the ltrate was pouredinto 10% NaHCO3 (30 mL) and extracted with ethyl acetate(30 mL3). The combined organic extracts were dried over MgSO4,ltered, and concentrated. The residue was eluted with ethyl ace-tate/hexane (v/v10/90) through a silica gel column to give thecorresponding pure quinoxaline. Quinoxaline structures werecharacterized by 1H NMR, 13C NMR, FTIR, and GCeMS, and weremostly known compounds. For unknown compounds, elementalanalysis data were additionally obtained. 4.2.1. 2,3-Dimethylquinoxaline (5).19,31aef Yield 87%. Yellow solid,mp 109e110 C (lit.31f mp 105 C). TLC (10% ethyl acetate/hexane) Rf0.30; 1H NMR (400 MHz, CDCl3) d 7.91 (dd, 2H, J6.3, 3.5 Hz), 7.59(dd, 1H, J6.3, 3.5 Hz), 2.66 (s, 6H); 13C NMR (100 MHz, CDCl3)d 153.4, 141.0, 128.7, 128.2, 23.1; IR (KBr) 3109, 3078, 3030, 2995,2953, 2914, 1490, 1398, 1164 cm1;GCeMS m/z (rel intensity) 158(M, 99), 117 (100), 76 (28), 50 (12).

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:
Article; Go, Ahra; Lee, Geunsoo; Kim, Jaeho; Bae, Seolhee; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 71; 8; (2015); p. 1215 – 1226;,
Nitrile – Wikipedia,
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Adding some certain compound to certain chemical reactions, such as: 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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 127946-77-4. 127946-77-4

Into a 25-mL round-bottom flask, were placed (1R,2R)-2-(2-(5-chloropyridin-3-yl)-5-(4- (1,1 -dioxidothiomorpholino)phenyl)thiazol-4-yl)-4,4-difluorocyclohexanecarboxylic acid (10.0 mg, 0.018 mmol, 1.00 equiv), 1-aminocyclopropanecarbonitrile hydrochloride (12.0 mg, 0.101 mmol, 5.74 equiv), HATU (16.0 mg, 0.042 mmol, 2.39 equiv), DIPEA (26.0 mg, 0.20 1 mmol, 11.4 equiv) and DMF (1.5 mL). The resulting mixture was stirred for 16 h at ambienttemperature and diluted with ethyl acetate (5.0 mL). The resulting mixture was washed with brine (5.0 mL). The aqueous layer was extracted with ethyl acetate (3 x 10.0 mL). The combined organic layers were washed with brine (3 x 10.0 mL), dried (Na2504), filtered, and concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography using ethyl acetate/petroleum ether (1:1). This resulted in 3.00mg (27%) of(1R,2R)-2-(2-(5-chloropyridin-3 -yl)-5 -(4-( 1,1 -dioxidothiomorpholino)phenyl)thiazol-4-yl)-N-( 1- cyanocyclopropyl)-4,4-difluorocyclohexanecarboxamide (Compound 2) as a light yellow solid:?H NMR (300 MHz, CDC13) Sppm 9.12 (s, 1H), 8.63 (s, 1H), 8.27 (s, 1H), 7.44 (d, J 9.0 Hz, 2H), 7.02 (d, J= 9.0 Hz, 2H), 5.92 (brs, 1H), 4.08-3.90 (m, 4H), 3.62-3.45 (m, 1H), 3.22-3.11 (m, 4H), 2.91-2.78 (m, 1H), 2.35-2.18 (m, 3H), 2.13-1.91 (m, 3H), 1.48-1.21 (m, 2H), 0.92-0.83(m, 2H); MS (ES, m/z): 632.1 (M + 1), 634.1 (M + 1).

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 1-Amino-1-cyclopropanecarbonitrile hydrochloride.

Reference:
Patent; MERCK SHARP & DOHME CORP.; STACHEL, Shawn; PAONE, Daniel, V.; LI, Jing; GINNETTI, Anthony; LIM, John; FU, Jianmin; XU, Shimin; WO2015/54038; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts