Category: nitriles-buliding-blocks

Application of 5312-97-0, A common heterocyclic compound, 5312-97-0, name is 2,5-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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.

Intermediate 42a) To solution of 2,5-dimethoxybenzonitrile (1.5 g) in dry Et20 (7 mL) was added propyl magnesium chloride (2 M in Et20, 9.2 mL) and the resulting mixture was heated to 40 C for 2 h. The mixture was chilled and 4 M HCI (9 mL) was carefully added and it was stirred at ambient temperature for 16 h. The mixture was extracted with EtOAc, the combined organic layers were washed with water, were dried and the volatiles were removed under reduced pressure. The residue was purified by column chromatography (Interchim cartridge 15SiHP / 120 g, Cy / EtOAc) to yield the desired compound (57% yield). LC-MS {Method 1): m/z [M+Hf = 209.3 (MW calc. = 208.25); R, = 3.5 min.

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; GRUeNENTHAL GMBH; NORDHOFF, Sonja; WACHTEN, Sebastian; KLESS, Achim; VOSS, Felix; RITTER, Stefanie; WO2014/108336; (2014); A1;,
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Synthetic Route of 35764-15-9, These common heterocyclic compound, 35764-15-9, name is 2-Bromo-4-(trifluoromethyl)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.

Into a 5 mL microwave vial were charged methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (300 mg, 0.85 mmol), 2-bromo-4- (trifluoromethyl)benzonitrile (425 mg, 1.70 mmol), cesium carbonate (1.38 g, 4.25 mmol), tetra-n- butylammonium iodide (314 mg, 0.85 mmol), POPd (43 mg, 0.085 mmol), water (0.6 mL) and NN- dimethylformamide (3 mL). The reaction mixture was subjected to microwave irradiation at 150 0C for 10 mins. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was washed with brine, dried, and concentrated under reduced pressure to afford the residue which was purified by silica gel column to yield the title compound.

The synthetic route of 35764-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; WEI, Zhi-Liang; GOWLUGARI, Sumithra; KAUB, Carl; WANG, Zhan; CAO, Yeyu; KINCAID, John; WO2010/33168; (2010); A2;,
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Application of 262298-02-2,Some common heterocyclic compound, 262298-02-2, name is 4-Methoxy-2-methylphenylacetonitrile, molecular formula is C10H11NO, 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.

Reference example 2 1-cyano-1-(2-methyl-4-methoxyphenyl)propan-2-one Under argon atmosphere, to a solution of the compound prepared in reference example 1 (11.7 g) in ethyl acetate (60 ml), metallic sodium (2.3 g) was added in numbers. The mixture was stirred for 2 hours at 50 §C. Ethyl acetate (40 ml) was added to the reaction mixture, and the mixture was refluxed for 2.5 hours and then it was stirred overnight at room temperature. A precipitation matter was collected by filtration, and it was washed with diethyl ether. The obtained crystal was dissolved into water (300 ml). The solution was adjusted pH 4 by adding 2N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated to give the title compound (12.06 g) having the following physical data. TLC: Rf 0.45 (n-hexane: ethyl acetate = 1: 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methoxy-2-methylphenylacetonitrile, its application will become more common.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1354884; (2003); 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. 10365-94-3, name is 1,3,5-Benzenetricarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3,5-Benzenetricarbonitrile

(3) 100 g of 1,3,5-benzotrinitrile and 3 g of Raney-Ni, 400 mL of ethanol are added to a 1 L hydrogenation reactor, and H2 is continuously charged, so that the pressure of the system is always maintained at 8 MPa during the reaction. After the reaction was performed at a reaction temperature of 110 C. for 1.5 h, the temperature was lowered. When the temperature in the reaction vessel was lowered to room temperature, the gas was purged, and 1,3,5-benzenetrimethylamine (having a purity of 99% or more) was obtained by filtration and recrystallization. The yield was 88% by weight.

According to the analysis of related databases, 10365-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sinopec Yangzi Petrochemical Co., Ltd.; Sinopec Corporation; Sun Hailong; Li Na; Gao Yilong; Wei Yanyu; Chen Xinhua; Miao Jun; Kan Lin; Bai Jiye; Chen Shaohui; Yang Aiwu; Xu Yuexing; (30 pag.)CN105001032; (2018); B;,
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Related Products of 354814-19-0, 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. 354814-19-0 name is 5-Amino-2-(trifluoromethyl)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.

Method 6; To a solution of 5-amino-2-trifluoromethylbenzonitrile (380 mg, 2.04 mmol) in pyridine (5 mL) was added 2-trifluoromethylbenzenesulfonyl chloride (500 mg, 2.04 mmol) and DMAP (25 mg, 0.204 mmol). The reaction mixture was stirred at room temperature for 48 hours. The reaction was quenched by the addition of 2M HCI (aq) (50 mL) and the mixture extracted into EtOAc (50 mL). The organic layer was collected, washed with 2M HCI (aq) (50 mL) and concentrated in vacuo. The residue was purified using reverse phase chromatography eluting with 10-60% (0.1 % ammonium hydroxide in MeCN) in water to afford the title compound as a colourless solid (318 mg, 40%). 1H NMR (400M Hz, CDCI3): delta ppm 7.19 (d, 1 H), 7.40 (d, 1 H), 7.56 (d, 1 H), 7.62 (d, 1 H), 7.64-7.78 (m, 2H), 7.91 (dd, 1 H), 8.20 (dd, 1 H). MS m/z 393 [M-H]-

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Amino-2-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; PFIZER LIMITED; OWEN, Robert McKenzie; STORER, Robert Ian; (82 pag.)WO2016/34971; (2016); 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. 39263-32-6, name is 2-Amino-5-bromobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 39263-32-6

Using a literature procedure described in the following literature reference which is herein incorporated by reference in its entirety for all purposes as if fully set forth herein, a dry round bottom flask was charged with 2-amino-5-bromo benzonitrile (1 equivalent) and zinc cyanide (2 equivalents), and DMF was added: J. Med. Chem. 2000,43, 4063. Nitrogen was bubbled through the solution for 5 minutes, and Pd [P (Ph) 3] 4 was added in one portion. The reaction mixture was stirred at 90 C overnight. After cooling to room temperature, saturated NAHC03 was added, and the mixture was extracted with EtOAc. The organic extracts were collected and dried (NA2SO4). Evaporation of the solvent under reduced pressure and purification by column chromatography on silicagel (2% methanol in methylene chloride) afforded the desired 4-aminobenzene-1, 3-DICARBONITRILE as a white solid. GC/MS M/Z : 143 (M+, 100%), Rt 14.7 minutes

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; CHIRON CORPORATION; WO2004/18419; (2004); A2;,
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Reference of 19295-57-9, The chemical industry reduces the impact on the environment during synthesis 19295-57-9, name is 3-Hydroxy-2,2-dimethylpropanenitrile, I believe this compound will play a more active role in future production and life.

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed 3-hydroxy-2,2-dimethylpropanenitrile (10.4 g, 104.91 mmol, 3.00 equiv). This was followed by the addition of FeCl3 (566.5 mg, 3.49 mmol, 0.10 equiv) in portions. The mixture was stirred for 1 h at room temperature. To this was added 174.1 (8 g, 34.92 mmol, 1.00 equiv) dropwise with stirring at 0 C. in a water/ice bath. The resulting solution was stirred for 1 h at room temperature. The resulting solution was diluted with 200 mL of H2O. The resulting solution was extracted with 3×200 mL of MTBE and the organic layers combined and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:8). The crude product was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-1): Column, Flash-C18; mobile phase, CH3CN_H2O=10:90 increasing to CH3CN_H2O=100:0 within 35 min; Detector, UV 254 nm. This resulted in 7.1 g (62%) of 174.2 as yellow oil.

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, 3-Hydroxy-2,2-dimethylpropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gilead Apollo, LLC; Ghosh, Shomir; Greenwood, Jeremy Robert; Harriman, Geraldine C.; Leit De Moradei, Silvana Marcel; (290 pag.)US2017/166584; (2017); A1;,
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Synthetic Route of 32446-66-5,Some common heterocyclic compound, 32446-66-5, name is 4,4′-Dicyanobenzophenone, molecular formula is C15H8N2O, 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.

4-[(4-Cyanophenyl)methanehydrazonoyl]benzonitrile (8u). To a mixture of 4-[(4- eyanophenyl)earbonyl]benzonitrile (6u) (0.56 g, 2.4 mmol) and EtOH (30 ml) hydrazine monohydrate (1.8 g, 36 mmol) was added dropwise over 5 mm. The yellow solution wasstirred overnight (about 16 h) at 80C, the mixture was allowed to cool to rt and EtOAe (150 ml) was added. The organic layer was washed with water (50 ml + 2 x 25 ml). The inorganic wash layers were extracted with EtOAe (2 x 25 ml). The organic layers were combined, washed neutral with aq. sat. NaC1 (25 ml), dried over Na2SO4 and concentrated at reduced pressure to afford a slightly red solid 8u (0.51 g, 86%).

The synthetic route of 32446-66-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALLOCYTE PHARMACEUTICALS AG; BREITENSTEIN, Werner; HUERZELER, Marianne; KELLY, Terence; MANCUSO, Riccardo; SCHNEIDER, Gisbert; WEITZ-SCHMIDT, Gabriele; WO2015/189265; (2015); 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. 34662-30-1, name is 3-Chloro-5-nitrobenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3-Chloro-5-nitrobenzonitrile

3-Chloro-5-nitrobenzonitrile (30.0 g) was dissolved in a mixture of water (85 mL) and H2SO4 (250 mL) and heated under an N2 atmosphere at 150 C. for 2 h. The mixture was cooled to ambient temperature and poured onto ice (1 L). The resulting solid was collected by vacuum filtration, and the filtrate was extracted with ethyl acetate. The extract and solid were combined, washed with water and brine, then were dried over MgSO4, filtered, and evaporated. The residue was dissolved in 1:1 water/MeOH (200 mL) with heating, treated with decolorizing charcoal and filtered. Water (100 mL) was added and the mixture was allowed to cool and crystallize. The product was obtained as pale yellow crystals. 1H-NMR (d6-DMSO): delta 14.00 (1H, br s), 8.51 (2H, m), 8.29 (1H, m). 13C-NMR (d6-DMSO): delta 164.9, 149.2, 135.2, 135.0, 134.5, 127.7, 122.9.

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; Ashley, Gary W.; Menzella, Hugo; Wee, Janice Lau; Carney, John R.; US2008/188450; (2008); 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. 34662-24-3, name is 2-Chloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Chloro-3-nitrobenzonitrile

To a solution of 2-chloro-3-nitrobenzonitrile (200 mg, 1 .3 mmol) in absolute THF (20 mL) was added dropwise BH3SMe2 (0.2 mL, 2.6 mmol) under nitrogen atmosphere protection. The mixture was stirred at reflux for 2 hrs. Then 2 N HCI (1 .5 mL) was added to the mixture and the mixture was stirred at reflux for 1 hour. The mixture was condensed to crude compound CI-1 -5B (248 mg) as yellow solid.

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 34662-24-3.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; HENDRICKSON, Thomas, Francis; HO, Koc-Kan; SAUNDERS, Michael, David; STEVENS, Brian, John; SWIERCZEK, Krzysztof; WRIGHT, Kevin, Bret; WO2013/62945; (2013); A1;,
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