Category: nitriles-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 97582-88-2, name is 3-(Difluoromethoxy)benzonitrile, 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 97582-88-2, Safety of 3-(Difluoromethoxy)benzonitrile

(1) A Grignard reagent prepared by using 0.75 g of magnesium, 4.46 g of 2-bromopropane and 24 ml of anhydrous diethyl ether, was dropwise added to a mixture comprising 4.09 g of 3-difluoromethoxybenzonitrile and 20 ml of anhydrous diethyl ether. After completion of the dropwise addition, the mixture was reacted at room temperature for 27 hours. The reaction mixture was put into ice water, and 6N sulfuric acid was added to bring the mixture to be weakly acidic, followed by stirring for 0.5 hour. The mixture was extracted with diethyl ether and washed with water. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=l/19), to obtain 2.04 g of 3-difluoromethoxyisobutyrophenone. The NMR spectrum data of this product is as follows.XH-NMR 5ppm (Solvent: CDCl3/300 MHz)1.23(d,6H),3.52(m,lH),6.56(t,lH),7.32(dd,lH),7.48(t, 1H),7.70(s,lH),7.80(d,lH)

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; ISHIHARA SANGYO KAISHA, LTD.; WO2006/16708; (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. 51632-12-3, name is 2-(4-Bromophenyl)-3-methylbutanenitrile, A new synthetic method of this compound is introduced below., Formula: C11H12BrN

SYNTHESIS EXAMPLE 2 4-Bromo-alpha-isopropyl-phenylacetic acid 20 g of 4-bromo-alpha-isopropylphenylacetonitrile was heated with 140 ml of sulfuric acid (50V/V%) at 145 C for 6 hours. The cooled reaction mixture was poured onto 150 g of ice, and extracted with ether (100 ml * 3). The ether layers were combined and extracted with three 70 ml portions of cold 5% sodium hydroxide solution, and the aqueous extracts were acidified with concentrated hydrochloric acid, and then extracted with ether. The ether extract was washed successively with water, saturated sodium chloride solution, dried over anhydrous sodium sulfate. Removal of the solvent gave 16.9 g (78.2%) of white crystals, which were sufficiently pure for use in next step. A portion of the crystals was recrystallized from benzene, melting point: 97 – 98 C.

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; Sumitomo Chemical Company, Limited; US3996244; (1976); A;,
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Reference of 69797-49-5, The chemical industry reduces the impact on the environment during synthesis 69797-49-5, name is 2-Amino-3-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

To a solution of 2-amino-3- methylbenzonitrile (0.85 g, 6.4 mmol) in THF (17 ml) was added triethylamine (0.99 ml, 7.1 mmol) followed by phosgene (20 % in toluene, 3.41 ml, 6.4 mmol). The RM was heated at reflux for 4 h then allowed to cool to RT. The THF was evaporated in vacuo and the residue precipitated with cold pentane. The resulting mixture was filtered and the filtrate evaporated to give the title compound as a yellow oil. Y = 74 %. MS ES+: 232.0 (compound analysed in diethylamine to generate diethyl urea).

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, 2-Amino-3-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NODTHERA LIMITED; BOCK, Mark G.; WATT, Alan Paul; PORTER, Roderick Alan; HARRISON, David; (229 pag.)WO2019/25467; (2019); A1;,
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Application of 1114546-30-3, These common heterocyclic compound, 1114546-30-3, name is 4-Bromo-2-fluoro-3-methylbenzonitrile, 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.

Reference Example 3 4-[(2S,3S)-3-(tert-butyldimethylsilyloxy)-2-methyl-5-oxopyrrolidin-1-yl]-2-fluoro-3-methylbenzonitrile To a solution of 4-bromo-2-fluoro-3-methylbenzonitrile (1.10 g), (4S,5S)-4-(tert-butyldimethylsilyloxy)-5-methylpyrrolidin-2-one (1.18 g), cesium carbonate (2.51 g), tris(dibenzylideneacetone)dipalladium(0) (235 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (297 mg) in dioxane (30 mL) was stirred under an argon atmosphere at 80 C. for 8 hr. 5 The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound as a colorless solid (yield: 347 mg, 19%). 1H-NMR(CDCl3)delta:0.11(6H,d,J=7.2 Hz), 0.91(9H,s), 1.04(3H,d,J=6.4 Hz), 2.19(3H,d,J=2.3 Hz), 2.50(1H,dd,J=16.8,2.4 Hz), 2.78(1H,dd,J=16.8,5.4 Hz), 4.09-4.22(1H,m), 4.44-4.50(1H,m), 6.96(1H,d,J=8.7 Hz), 7.45-7.53(1H,m).

The synthetic route of 1114546-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; US2009/42967; (2009); 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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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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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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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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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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Synthetic Route of 133541-45-4, A common heterocyclic compound, 133541-45-4, name is 4-Bromo-2,5-difluorobenzonitrile, molecular formula is C7H2BrF2N, 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.

(0527) To a stirred suspension of (R)-4-phenyloxazolidin-2-one (100 mg, 0.613 mmol), 4- bromo-2,5-difluorobenzonitrile (134 mg, 0.613 mmol), copper(I) iodide (175 mg, 0.919 mmol), and potassium carbonate (254 mg, 1.84 mmol) in anhydrous 1,4-dioxane (3.0 mL) under an atmosphere of nitrogen was added (1S,2S)-(+)-N,N’-dimethylcyclohexane-1,2-diamine (0.29 mL, 1.8 mmol) and the resulting mixture was heated at 90 C for 20 h. After cooling to ambient temperature the mixture was filtered through a pad of Celite and the filtered solids were washed with ethyl acetate (30 mL). The combined filtrates were evaporated to dryness in vacuo and the crude residue was purified by flash silica gel chromatography (ISCO CombiFlash Rf Purification System; 12 g SepaFlash Silica Flash Column, eluting with a 0-50% ethyl acetate in hexanes gradient) to afford the title compound as an oil. MS (ESI) m/z [M+H+CH3CN]+: 342.2.

The synthetic route of 133541-45-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALJI, Abbas; BERGER, Richard; STUMP, Craig, A.; SCHLEGEL, Kelly Ann, S.; MULHEARN, James, J.; GRESHOCK, Thomas, J.; WANG, Deping; FRALEY, Mark, E.; JONES, Kristen, G.; (273 pag.)WO2017/222951; (2017); A1;,
Nitrile – Wikipedia,
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