Author: Jessica.F

Related Products of 354814-19-0,Some common heterocyclic compound, 354814-19-0, name is 5-Amino-2-(trifluoromethyl)benzonitrile, molecular formula is C8H5F3N2, 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 38: 2-{[3-Cyano-4-(trifluoromethyl)phenyl]amino}-2-oxoethyl acetate; Triethylamine (1.09 g, 10.8 mmol) was added to a stirred solution of 5-amino-2- (trifluoromethyl)benzonitrile (Intermediate 37, 1.0 g, 5.37 mmol) in DCM (40 mL), at 0C, and the mixture was stirred for 15 min. Chloro-2-oxoethyl acetate (1.10 g, 8.06 mmol) was added at 0C and the mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with DCM and washed with ice water, and saturated brine solution. The organic layer was dried over anhydrous Na2S04, and concentrated under reduced pressure to afford the crude compound. This was purified by column chromatography (100-200 mesh silica gel), eluting with 20%-40% EtOAc/pet. ether to give the title compound (1.1 g).MS ES+ve m/z 285 (M-H).1H NMR (400 MHz, Chloroform-d) delta ppm 2.26 (s, 3 H), 4.76 (s, 2 H), 7.72-7.82 (m, 1 H), 7.90-8.00 (m, 1 H), 8.08-8.18 (m, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Amino-2-(trifluoromethyl)benzonitrile, its application will become more common.

Reference:
Patent; CONVERGENCE PHARMACEUTICALS LIMITED; BESWICK, Paul John; GLEAVE, Robert James; HACHISU, Shuji; VILE, Sadie; BERTHELEME, Nicolas; WARD, Simon E; WO2012/4604; (2012); 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. 58949-75-0, name is 4-(2-Oxopropyl)benzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

EXAMPLE 47 2-[(Aminocarbonyl)amino]-4-methyl-5-(4-cyanophenyl)-3-thiophenecarboxamide Prepared by the method of Example 26 from (4-cyanophenyl)acetone. MS (ES) 299 (M-H)-.

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; Baxter, Andrew; Brough, Stephen; Faull, Alan; Johnstone, Craig; McInally, Thomas; US2002/107252; (2002); A1;,
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175596-01-7, name is Methyl 4-cyano-2-fluorobenzoate, 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. Recommanded Product: 175596-01-7

Step (ii) Raney nickel (2.0 g) was added to a solution of methyl 4-cyano-2-fluorobenzoate (obtained as described in step (i) above) (10.1 g, 61.6 mmol) in acetic acid (200 ml.) and water (100 niL). The mixture was stirred at RT under argon at 20 bar. After 18 h the mixture was filtered through diatomaceous earth, washing through with water (1000 mL). The filtrate was extracted with EtOAc (3 chi 300 mL). The combined organic phases were dried and concentrated, adding toluene to assist removal of acetic acid, to give methyl 2- 11 uoro-4-( hydroxy meth) l)benzoate (crude, 6.06 g) which was used in the next step without further purification or characterisation.

The synthetic route of 175596-01-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; TAKEDA CAMBRIDGE LIMITED; BUFFHAM, William; CANNING, Hannah; DAVENPORT, Richard; FARNABY, William; MACK, Stephen; PARMAR, Alka; WRIGHT, Susanne; WO2015/25164; (2015); A1;,
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Related Products of 191014-55-8, 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. 191014-55-8 name is 4-Fluoro-2-methoxybenzonitrile, 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.

A solution of (S)-3-(l-aminoethyl)-6-chloroquinolin-2(lH)-one hydrochloride II-l (201 mg, 0.776 mmol) and 4-fluoro-2-methoxybenzonitrile (236 mg, 1.56 mmol) in DMSO (5 ml) was treated with DIEA (400 mu, 2.29 mmol) and stirred at 110 C for three days. The sample was diluted with water (75 mL) and extracted with DCM (2×50 mL), dried, and filtered. Silica gel was added, and the solvent was evaporated under reduced pressure. The material was chromatographed by Biotage MPLC (silica gel, 0 to 70% EtOAc in hexanes, with isocratic elution when peaks came off) to provide a gum. The material was dissolved in DCM (10 mL), washed with water (2×10 mL), dried (Na2S04), filtered, and evaporated to provide 76 mg yellow powder. The sample was mixed with MeCN (4 mL) and water (2 mL), frozen on a dry ice/acetone bath, and lyopholyzed to provide the title compound 1-2 (71.1 mg, 0.193 mmol, 24.93 % yield, HPLC purity 96.3% at 220 nm) as a solid. 1H NMR (300 MHz, DMSO-d6): delta ppm 12.07 (s, 1 H), 7.77 (d, J=2.35 Hz, 1 H), 7.74 (s, 1 H), 7.50 (dd, J=8.65, 1.91 Hz, 1 H), 7.35 – 7.20 (m, 3 H), 6.27 (s, 1 H), 6.06 (d, J=7.90 Hz, 1 H), 4.79 – 4.65 (m, 1 H), 3.75 (s, 3 H), 1.43 (d, J=6.45 Hz, 3 H). LCMS (Method 1): Rt 2.37 min., m/z 354.0 [M+H]+.

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

Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (141 pag.)WO2016/44782; (2016); A1;,
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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. 129931-47-1, name is 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. COA of Formula: C8H2ClF4N

(c) 1-(2-Chloro-6-cyano-4-trifluoromethylphenyl)-4-pentafluoroethylpyrimidin-6-one (compound No 4 in Table I) was prepared by the reaction of 3-chloro-4-fluoro-5-cyano-trifluoromethylbenzene and 4-pentafluoroethylpyrimidin-6-one. 1 H NMR delta(CDCl3 /d6 -DMS0): 8.15 (1H,s); 8.09 (2H,m); 7.09 (1H,s).

The synthetic route of 129931-47-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Imperial Chemical Industries PLC; US5109004; (1992); A;,
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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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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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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 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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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 64113-85-5 as follows. category: nitriles-buliding-blocks

General procedure: The heterocyclic derivative (0.99 mmol) and 5 mL THF is cooled to -78 oC, n-BuLi solution ( 0.5, mL, 1.2 eq) is added, the mixture is stirred 1 hr, after which 2-cyano-4-methyhlbiphenyl (192 mg, 0.99 mmol, dissolved in 5 mL THF) is added dropwise, The solution is then stirred 1 hr at -78 oC, then allowed to warm to room temperature and stirred for 6 hr. After this, 10 mL of 6M HCl is added and the mixture is stirred overnight. The solution is then basified with 10M NaOH and the products are partitioned between ether and water. The aqueous layer is further extracted (2x with ether) and the combined extracts are washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent is then removed under reduced pressure and the crude mixture is purified by column chromatography (1:1, hexanes: ethyl acetate).

According to the analysis of related databases, 64113-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Stentzel, Michael R.; Klumpp, Douglas A.; Tetrahedron Letters; vol. 60; 25; (2019); p. 1675 – 1677;,
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