Category: nitriles-buliding-blocks

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: 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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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;,
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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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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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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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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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These common heterocyclic compound, 134227-45-5, name is 3,4,5-Trifluorobenzonitrile, 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. 134227-45-5

Example 177A 3,5-difluoro-4-(4-morpholinyl)benzylamine The title compound was prepared using the procedures described in Examples 172A and 172B using 3,4,5-trifluorobenzonitrile instead of 4-fluorobenzonitrile.

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 134227-45-5.

Reference:
Patent; Lee, Chih-Hung; Bayburt, Erol K.; DiDomenico JR., Stanley; Drizin, Irene; Gomtsyan, Arthur R.; Koenig, John R.; Perner, Richard J.; Schmidt JR., Robert G.; Turner, Sean C.; White, Tammie K.; Zheng, Guo Zhu; US2004/157849; (2004); A1;,
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194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 194853-86-6

A mixture of 4-fluoro-2- (trifluoromethyl) benzonitrile (0.158 g, 0.84 mmol), 3,3, 3- TRIFLUOROPROPYLAMINE. HCI (0.125 g, 0.84 mmol) and DIEA (0.326 g, 2.52 MMOL) in DMSO (1.5 mL) was heated under nitrogen in a microwave at 200C for 20 min. The mixture was partitioned between Et2O and 0. 1 N HCI. The organic phase was washed with 0. 1 N HCI (twice) and brine, dried (NA2SO4), and concentrated in vacuo. The residue was purified by silica gel chromatography (0-50% EtOAc-hexane gradient) and the product crystallized from ET2O-HEXANES to give the title compound as a white solid (0.144 g, 61% yield): 1H NMR (400 MHz, CDCI3) 8 7.60 (d, J = 8.6 Hz, 1 H), 6.87 (d, J = 2.4 Hz, 1 H), 6.71 (dd, J = 8.6, 2.4 Hz, 1 H), 4.56 (bs, NH), 3.53 (q, J = 6.5 Hz, 2H), 2.51-2. 40 (m, 2H); MS (ES) M/Z 283 (M+1).

Statistics shows that 194853-86-6 is playing an increasingly important role. we look forward to future research findings about 4-Fluoro-2-(trifluoromethyl)benzonitrile.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/795; (2005); A2;,
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The chemical industry reduces the impact on the environment during synthesis 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, I believe this compound will play a more active role in future production and life. 1813-33-8

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 chemical industry reduces the impact on the environment during synthesis 1813-33-8. I believe this compound will play a more active role in future production and life.

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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