Month: March 2021

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 6575-11-7, name is 2-Amino-6-chlorobenzonitrile, 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 6575-11-7, Formula: C7H5ClN2

EXAMPLE 43 9-Amino-8-chloro-4-oxo-1,2,3,4-tetrahydroacridine Following the method of Example 7, but substituting 2-amino-6-chlorobenzonitrile for anthranilonitrile, afforded the title compound (15%, m.p. 205 C.). 1 H-NMR (CDCl3, 300 MHz,delta): 1H, d, 7.62 ppm (J=7 Hz); 1H, t, 7.31 ppm (J=7 Hz); 1H, d, 7.19 ppm (J=7 Hz); 2H, bs, 5.81 ppm; 2H, t, 4.31 ppm (J=6 Hz); 2H, t, 2.52 ppm (J=6 Hz); 2H, m, 2.11 ppm; HRMS: Calculated–234.0560; Found–234.0565; TLC: (ethyl acetate) Rf -0.27.

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

Reference:
Patent; Pfizer Inc.; US5202440; (1993); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 3939-09-1, name is 2,4-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C7H3F2N

A mixture of 2, 4-Difluoro-benzonitrile (1.39 g, 10 mmol) , 3- amino-propane-1, 2-diol (0.911 g, 10 mmol) , and ethyl- diisopropyl-amine (1.74 mL) in DMSO (10 itiL) was microwaved at 200 0C for 7 min. Then the reaction mixture was poured into a saturated NH4Cl aq. solution (100 mL) , extracted with EtOAc (3×100 mL) , dried over Na2SCu, filtered, concentrated. The crude mixture was purified by flash silica gel chromatography (EtOAc-Hexane 1:1) to give 2- (2, 3-Dihydroxy-propylamino) -4- fluoro-benzonitrile (0.87 g, 41.4% yield). LCMS (m/z) : M+H = 211.To a mixture of 6, 6-Dimethyl-3-trifluoromethyl-l, 5, 6, 7- tetrahydro-indazol-4-one (0.961 g, 4.14 mmol, 1 eq) and NaH (99 ?ig, 4.14 mmol, 1 eq) in dimethyl acetamide (20 mL) was added slowly 2- (2, 3-Dihydroxy-propylamino) -4-fluoro- benzonitrile (0.87 g, 4.14 mmol, 1 eq) . Then the reaction mixture was stirred at 150 C overnight, cooled, poured into saturated NH4Cl aq. solution (100 mL) , extracted by EtOAc(3×150 mL) , dried over Na2SO4, filtered, concentrated. The crude product was purified by flash silica gel chromatography, eluted by EtOAc to give 2- (2, 3-Dihydroxy-propylamino) -4- (6, 6- dimethyl-4-oxo-3-trifluoromethyl-4 , 5,6, 7-tetrahydro-indazol-l- yl)-benzonitrile (1.7g, 97% yield). LCMS (m/z): M+H = 423. 2- (2, 3-Dihydroxy-propylamino) -4- (6, 6-dimethyl-4-oxo-3- trifluoromethyl-4, 5, 6, 7-tetrahydro-indazol-l-yl) -benzonitrile (1.7 g, 4 mmol, 1 eq) , NaOH (806 mg, 20 mmol, 5 eq) , and H2O2 EPO (3 iriL) were dissolved in EtOH-water (4:1) (40 itiL) . The mixture was microwaved at 120 C for 15 min, then concentrated to dryness, and purified by flash chromatography, eluted by 10% MeOH in EtOAc to give pure 2- (2, 3-Dihydroxy-propylamino) – 4- (6, beta-dimethyl-4-oxo-3-trifluoromethyl-4, 5, 6, 7-tetrahydro- indazol-1-y l)-benzamide (0.52 g, 29% yield). LCMS (m/z) : M+H = 441.

The synthetic route of 3939-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SERENEX, INC.; WO2006/91963; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 71825-51-9, name is 2-Methyl-2-(4-nitrophenyl)propanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Methyl-2-(4-nitrophenyl)propanenitrile

16 g (84.1 mmol) of 2-methyl-2-(4-nitro-phenyl)-propionitrile (Example 1d) and 4.16 g of Raney-Ni are shacked in 160 ml of THF-MeOH (1 :1) under 1.1 bar of H2 for 12 h at rt. After completion of the reaction, the catalyst is filtered-off and the filtrate is evaporated to dryness. The residue is purified by flash chromatography on silica gel (hexane-EtOAc 3:1 to 1 :2) to provide the title compound as an oil. ES-MS: 161 (M + H)+; analytical HPLC: W= 2.13 minutes (Grad 1).

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 71825-51-9.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/122806; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts