Category: nitriles-buliding-blocks

Electric Literature of 1735-88-2, 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. 1735-88-2 name is 2-Cyano-N-(4-fluorophenyl)acetamide, 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.

To a solution of 2-cyano-N- (4-fluorophenyl) acetamide (2 g, 11.2 mmol) and (3E) -4-ethoxy-l, 1, 1-trifluorobut-3-en-2-one (2.26 g, 13.4 mmol) in dimethyleneglycol monomethylether (20 mL) was added 1, 4-diazabicyclo [2.2.2] octane (1.26 g, 11.2 mmol), and the mixture was stirred at 120C for 6 hr. The reaction mixture was diluted with IN hydrochloric acid and ethyl acetate, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=l/2->1/1) to give a white solid. The white solid was washed with ethyl acetate and collected by filtration to give the title compound (230 mg, 7.2%) as a white solid. 1H-NMR (DMSOd6, 300 MHz) delta 7.13 (IH, d, J = 7.6 Hz), 7.32 – 7.46 (2H, m) , 7.49 – 7.60 (2H, m) , 8.44 (IH, d, J = 7.4 Hz) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Cyano-N-(4-fluorophenyl)acetamide, and friends who are interested can also refer to it.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2009/136663; (2009); 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. 3032-92-6, name is 4-Ethynylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Ethynylbenzonitrile

General procedure: To a low pressure reactor equipped with magnetic stirreralkyne (0.15 mmol), Cs2CO3(0.30 mmol), copper catalyst(0.0075 mmol), n-BuBr (0.18 mmol) and DMF (2 mL)were added. CO2(2 atm.) was introduced into the reactionmixture by triply purging the reactor with CO2.Thereaction mixture was stirred at 60 C for 6 h or 16 h. Afterthe reaction, the mixture was cooled to room temperatureand diluted with DMF. After centrifugation, the organicphase was concentrated under reduced pressure and purifiedby column chromatography on silica gel (eluent petroleumether/EtOAc 20:1). Isolated product was dried undervacuum.

According to the analysis of related databases, 3032-92-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bondarenko, Grigoriy N.; Dvurechenskaya, Ekaterina G.; Magommedov, Eldar Sh.; Beletskaya, Irina P.; Catalysis Letters; vol. 147; 10; (2017); p. 2570 – 2580;,
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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. 95-11-4, name is 5-Norbornene-2-carbonitrile, A new synthetic method of this compound is introduced below., name: 5-Norbornene-2-carbonitrile

Hydrogenation of nonborn-5-ene-2-carbonitrile 1d was performed similarly, using sodium borohydride (0.3 g, 0.008 mol), 15 mL of isopropanol, anhydrous nickel(II) chloride (0.5 g, 0.004 mol), and nitrile 1d (12 g, 0.1 mol). The reaction duration was 12 h, the temperature was 70C. 2-Aminomethylnorbornane 2d, content 5.5 wt %. Mass spectrum, m/e (Irel, %): 125 (27) [M], 108 (16), 95 (21), 79 (38), 66 (100), 56 (18). Bis(2-norbornylmethyl)amine 3d, content 89 wt %. Mass spectrum, m/e (Irel, %): 235 (13) [M+2], 234 (81) [M+1], 138 (100) [C7H11CH2NH=CH2]+, 109 (19), 67 (35), 44 (42). Tris(2-norbornylmethyl)amine 4d, content 2 wt %. Mass spectrum, m/e (Irel, %): 340 (1) [M-1], 246 (100) [M – C7H11], 152 (14), 109 (4), 79 (3), 67 (17).

The synthetic route of 95-11-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mokhov; Popov; Shcherbakova; Russian Journal of General Chemistry; vol. 86; 2; (2016); p. 273 – 280; Zh. Obshch. Khim.; vol. 86; 2; (2016); p. 245 – 252,8;,
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Related Products of 50670-64-9, A common heterocyclic compound, 50670-64-9, name is 5-Amino-2-methylbenzonitrile, molecular formula is C8H8N2, 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.

General procedure: The respective amine (1.1 equivalent) and methyl thioglycolate(1.0 equivalent) were added to an ice-cooled solution of 1,19-carbonyldiimidazole (1.1 equivalent) in 30 ml of absolute methylenechloride. The reaction mixture was stirred at room temperature for3 days and then washed three times with 3 M HCl. The solvent wasremoved, and the crude solid was purified by recrystallization fromtoluene or by flash column chromatography.

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:
Article; Oppermann, Sina; Schrader, Florian C.; Elsaesser, Katharina; Dolga, Amalia M.; Kraus, Anna Lena; Doti, Nunzianna; Wegscheid-Gerlach, Christof; Schlitzer, Martin; Culmsee, Carsten; Journal of Pharmacology and Experimental Therapeutics; vol. 350; 2; (2014); p. 273 – 289;,
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Reference of 94088-46-7, 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. 94088-46-7, name is 2-Fluoro-6-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-fluoro-6-methoxybenzonitrile (1.0 g, 6.62 mmol) and potassium carbonate (1.83 g, 13.23 mmol) in DMF (5 ml) was added 2- (trimethylsilyl)ethanethiol (1.27 ml, 7.94 mmol). The mixture was stirred at room temprature for 4 hours. The TLC indicated complete consumption of starting material. The mixture was filtered and the filtrate was concentrated under vacuum. The crude was adsorbed onto silica gel, and purified by silica gel column with hexane and ethyl acetate to give 2-methoxy-6-((2- (trimethylsilyl)ethyl)thio)benzonitrile. LC/MS [M+H]+:266.

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-Fluoro-6-methoxybenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MANDAL, Mihir; TANG, Haifeng; XIAO, Li; SU, Jing; LI, Guoqing; YANG, Shu-Wei; PAN, Weidong; TANG, Haiqun; DEJESUS, Reynalda; HICKS, Jacqueline; LOMBARDO, Matthew; CHU, Hong; HAGMANN, William; PASTERNAK, Alex; GU, Xin; JIANG, Jinlong; DONG, Shuzhi; DING, Fa-Xiang; LONDON, Clare; BISWAS, Dipshikha; YOUNG, Katherine; HUNTER, David, N.; ZHAO, Zhiqiang; YANG, Dexi; WO2015/112441; (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. 368-77-4, name is 3-(Trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-(Trifluoromethyl)benzonitrile

General procedure: In a glove box, a flame-dried GLC vial equipped with a magnetic stir bar is charged with[3a]+[BArF4]- (1.0 mol%) and Me2PhSiH (2a) (2.1 or 5.0 equiv). The indicated nitrile is added eitherin the glove box (for solid starting materials) or by micro syringe outside the glove box, and theresulting reaction mixture is maintained at room temperature for the indicated time. The reaction isquenched by the addition of a mixture of cyclohexane and tert-butyl methyl ether (90:10) containing4% Et3N (0.5 mL), and the resulting solution is filtered through a pad of Celite coated by a smalllayer of silica gel with a solution of cyclohexane and tert-butyl methyl ether (90:10) containing 4%Et3N (3-4 mL) as eluent. Solvents are removed under reduced pressure, and the residue isdissolved in Et2O (1 mL) followed by addition of HCl (2M in Et2O, 1.0 mL, 2.0 mmol, 10 equiv). Theresulting suspension is stirred for 1 h and filtered, affording the amines as hydrochloride salts aswhite to yellow solids.

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:
Article; Wuebbolt, Simon; Oestreich, Martin; Synlett; vol. 28; 18; (2017); p. 2411 – 2414;,
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Reference of 26830-96-6, 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. 26830-96-6, name is 2-Amino-4-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 120 4-(2-Cyano-5-methylanilino)-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine The title compound was prepared from a mixture of 4-chloro-2-(3-pyridinyl)-6-(trifluoromethyl)pyrimidine (50 mg, 0.193 mmol) and 2-cyano-5-methylaniline (38 mg, 0.290 mmol) similar to Example 117 and isolated as a yellow solid (8 mg, 12%). 1H NMR (CDCl3): 9.62-9.61 (m, 1H), 8.75-8.69 (m, 2H), 8.08 (s, 1H), 7.62 (s, 1H), 7.60 (d, J=8.1 Hz, 1H), 7.46-7.41 (m, 1H), 7.12 (dd, J=0.9, 8.1 Hz, 1H), 7.00 (s, 1H), 2.52 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Amino-4-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Cytovia, Inc.; US2003/69239; (2003); A1;,
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Application of 67515-59-7, 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. 67515-59-7 name is 4-Fluoro-3-(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.

General procedure: 4-fluoro-3-(trifluoromethyl)benzonitrile (1 equiv) and the alcohol (1 equiv) were added to a microwave vial and cooled in an ice bath, then 0.5M potassium tert-butoxide in tetrahydrofuran (1.1 equiv) was carefully added and allowed to warm to room temperature. The contents were then heated to 1 15 C for 1 minute in the microwave. After cooling, celite was added and the solvent was removed under reduced pressure. The resulting powder was subjected to flash chromatography on silica gel.

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

Reference:
Patent; THORPE, Steven Brandon; SANTOS, Webster L.; LYNCH, Kevin R.; (375 pag.)WO2017/172989; (2017); 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. 94088-46-7, name is 2-Fluoro-6-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Safety of 2-Fluoro-6-methoxybenzonitrile

General procedure: A mixture of benzonitrile 1 (10.0 mmol) and methylhydrazine (2.8 mL, 50.0 mmol) in EtOH (10.0 mL) was heated to reflux overnight. The mixture was cooled to rt and then concentrated. H2O (10.0 mL) and EtOAc (20.0 mL) were added to the residue. The organic layer was washed with H2O (10.0 mL), brine (10.0 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The residue was subjected to silica-gel chromatography by using EtOAc/hexanes (1:1) as eluent to give the product 2.

The synthetic route of 94088-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Han-Jun; Hung, Shiang-Fu; Chen, Chuan-Lin; Lin, Mei-Huey; Tetrahedron; vol. 69; 19; (2013); p. 3907 – 3912;,
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Some common heterocyclic compound, 623-03-0, name is 4-Chlorobenzonitrile, molecular formula is C7H4ClN, 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. Product Details of 623-03-0

The reaction substrate o-aminothiophenol (0.318 mL, 3 mmol) was accurately measured,P-chlorobenzonitrile (0.412 g, 3 mmol),Methanesulfonic acid (0.0028 g, 0.03 mmol),Followed by addition to a 25 mL Schlenk flask,And the mixture was allowed to stand in an oil bath at 40 C for 14 h.After the reaction was stopped, the mixture was extracted with water and ethyl acetate as an extractant,The extracted organic phase was dried with anhydrous Na2SO4 for 2 h,After removal of the solvent by rotary evaporation,To give the crude target product 2- (4-chloroaryl) benzothiazole.Followed by recrystallization step:The crude 2- (4-chloroaryl) benzothiazole was placed in a 50 mL flask.The flask was placed in a heating jacket and heated to 50 C,Slowly dropping anhydrous ethanol to its complete dissolution,The flask was then removed from the heating jacket and allowed to stand at room temperature for 4 h,To be white crystal precipitation after the full use of filter paper filter,To give the desired product 2- (4-chloroaryl) benzothiazole,The yield was 97%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 623-03-0, its application will become more common.

Reference:
Patent; Dalian University of Technology; Yu Xiaoqiang; Bao Ming; Feng Xiujuan; Pu Zichao; (10 pag.)CN104910098; (2017); B;,
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