Author: Jessica.F

Application of 873-74-5, A common heterocyclic compound, 873-74-5, name is 4-Aminobenzonitrile, molecular formula is C7H6N2, 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.

EXAMPLE 1 Preparation of 4-Amino-3,5-dibromobenzonitrile STR15 To a stirred solution of 100 mg (0.847 mmoles) of p-aminobenzonitrile in 3.6 mL dioxane chilled in an ice-bath was added sequentially 356 muL (1.78 mmoles) of 5 N sodium hydroxide solution and 284 mg (1.78 mmoles) of bromine. The ice-water bath was removed and the reaction mixture was stirred further for 1.5 hours. After this time, 21.8 muL (0.423 mmoles) of bromine was added to drive the reaction to completion and stirring was continued for 10 minutes. The mixture was partitioned between ethyl acetate and ice-water and the organic phase was separated. It was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated. Purification by plate layer chromatography using hexane-ethyl acetate (7:3) as eluant provided 175 mg (74%) of the entitled product. NMR(CDCl3) delta: 5.1 (bs, 2H), 7.66 (s, 2H).

The synthetic route of 873-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US5192758; (1993); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 118431-88-2, 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. 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a cooled solution of potassium ieri-butylate (91.6mmol, 1.1 equiv.) in THF (260ml) was added a solution of 3-cyclopropyl-3-oxo-propionitrile (83.2mmol, 1.0 equiv.) in THF (130ml) over 30 minutes, while maintaining the temperature at 0C. After stirring for an additional hour at 0C, the solution was cooled to -20C. The respective isothiocyanate (83.2mmol, 1.0 equiv.) was dissolved in THF (130ml) and added to the orange solution over 25 minutes. The reaction mixture was allowed to warm to room temperature. TLC indicated complete conversion of starting material. The clear solution was poured onto ice-cold IN HCl (1L), extracted with dichloromethane (1L), dried over Na2SO4 and evaporated to dryness. The resulting raw-solid was recrystallized from MTBE.

The chemical industry reduces the impact on the environment during synthesis 3-Cyclopropyl-3-oxopropanenitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ALGIAX PHARMACEUTICALS GMBH; HASSE, Birgit; KOOPMANS, Guido; (41 pag.)WO2015/140081; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 447-60-9, 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 447-60-9 as follows.

To a solution of 2,2,6,6-tetramethylpiperidine (0.99 g, 7.02 mmol) in THF (25 ml) was added n-BuLi (2.80 ml, 2.5 M hexane solution, 7.02 mmol) at -10 C. After stirring for 10 min, this solution was cooled to -78 C., tris(1-methylethyl)borate (1.58 g, 8.4 mmol) was added, and the mixture was stirred for 5 min. To this solution was added a solution of 2-(trifluoromethyl)benzonitrile (1.00 g, 5.85 mmol) in THF (10 ml), and the mixture was stirred at -78 C. for 2 hr. The reaction solution was allowed to warm to room temperature, the reaction was quenched with acetic acid, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, the precipitated solid was filtered off, and the filtrate was concentrated to give the title compound (3.14 g) as a mixture. This was used for the next reaction without performing further purification and identification.

According to the analysis of related databases, 447-60-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kasai, Shizuo; Kamaura, Masahiro; Cho, Nobuo; US2011/251187; (2011); 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. 159847-81-1, name is Methyl 2-amino-5-cyanobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H8N2O2

To a suspension of 3- (chlorosulfonyl) benzoic acid (10.8 g, 49.0 mmol) in CH2Cl2 (105 mL) and three drops [OF DMF] was added oxalyl chloride (12.5 mL) and the reaction was stirred at rt overnight. The solution was concentrated in vacuo, diluted with [CH2C12] (100 mL), and the solution was divided into two reactions. A 50 mL (24.5 mmol) aliquot of the acid chloride was added to a solution of PHA-522499 (4.49 g, 25.5 mmol) dissolved in [CH2C12] (50 mL) and pyridine (3.0 [ML)] and stirred at rt overnight. The solution was diluted with MTBE, washed with 2 N HC1 and brine, concentrated, [TRITURATED WITH MTBE] to afford 7.91 g [(85%)] of methyl [2-{[3-] (chlorosulfonyl) benzoyl] [AMINO}-5-CYANOBENZOATE] as a tan [SOLID. 1H NMR (400 MHZ,] [DMSO-D6)] [8] 11.73 (s, 1 H), 8.67 (d, [J=] 9 Hz, [1] H), 8.37 (d, [J=] 2 Hz, 1 H), 8.25 (s, 1 H), 8.12 (dd, J= 9,2 Hz, 1 H), 7.92 (d, J= 8 Hz, [1] H), 7. [88] (d, J= 8 Hz, 1 H), 7.60 (t, [J= 8 HZ, 1 H),] 3.93 (s, 3H).

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 159847-81-1.

Reference:
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/18414; (2004); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 2042-37-7, A common heterocyclic compound, 2042-37-7, name is 2-Bromobenzonitrile, molecular formula is C7H4BrN, 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: K3PO4 (5.62 mmol) in DMSO (4 mL), were added Cu(OAc)2 (0.28 mmol). The flask was evacuatedand backfilled with argon for three times. The resulting suspension was heated in a 80 C oil bathwith stirring for the indicated time. The reactor was cooled to r.t., the flask was opened to air and thereaction mixture was poured into water (20 mL), extracted with ethyl acetate (20 mL × 3), andorganic layer was washed with water (20 mL × 2) and once with brine (25 mL), dried overmagnesium sulfate and concentrated in vacuo. The product was purified by column chromatographyon silica gel using petroleum ether and ethyl acetate as eluent.1-(2-Methoxyphenyl)-1H-pyrrole (3a) [30]: colorless oil (0.43 g, 88%). 1H-NMR (400 MHz, CDCl3) delta (ppm):7.30-7.23 (2H, m), 7.03-6.98 (4H, m), 6.30 (2H,

The synthetic route of 2042-37-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yuan, Chunling; Zhang, Lei; Zhao, Yingdai; Molecules; vol. 24; 22; (2019);,
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. 17626-40-3, name is 3,4-Diaminobenzonitrile, A new synthetic method of this compound is introduced below., name: 3,4-Diaminobenzonitrile

In a round bottom flask (250ml) 3,4-dichloro-1-(hexadecan-6-yl)-1H-pyrrole-2,5-dione (10g, 25.6 mmol) wasdissolved under argon in 150ml of absolute ethanol. Sodium acetate (2.5g, 30.7mmol) and 3,4-diaminobenzonitrile (3.4g,25.6 mmol) were added. The mixture was stirred overnight at room temperature. Ethanol was removed by distillationunder vacuum at 40C and the crude product was purified by flash chromatography onto silica gel using hexane/methylene-chloride/ethylacetate 60/35/5 as the eluent. 2.5g of pure product were obtained as yellow wax with a yield of 21%. When conditions were made harsher by heating to reflux the final product (5) was obtained (yield 40%).

The synthetic route of 17626-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Solvay SA; Caille, Jean-Raphael; Dabeux, Francois; Bolsee, Jean-Christophe; Fenoll, Mathieu; EP2808327; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 874-89-5, The chemical industry reduces the impact on the environment during synthesis 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 × 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.

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, 4-(Hydroxymethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Khazdooz, Leila; Zarei, Amin; Aghaei, Hamidreza; Azizi, Ghobad; Gheisari, Mohammad Mehdi; Tetrahedron Letters; vol. 57; 2; (2016); p. 168 – 171;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 75344-77-3, 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. 75344-77-3, name is 4-Bromo-3,5-dimethylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Into a 500-mL 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, were placed 4-bromo-3,5-dimethylbenzonitrile (4 g, 19.04 mmol, 1.00 equiv) and dichloromethane (50 mL). This was followed by the addition of diisobutylaluminum hydride (40 mL) dropwise with stirring at -65C. The resulting solution was stirring for 2 h at room temperature. To the reaction mixture was added hydrogen chloride (5%, 40 mL) dropwise with stirring at room temperature. The resulting solution was heated to reflux for 30 min and then cooled to room temperature. The resulting solution was diluted with 200 mL of DCM. The organic layer was washed with 3×100 mL of brine and then dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 4 g (crude) of 4- bromo-3,5-dimethylbenzaldehyde as light 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, 4-Bromo-3,5-dimethylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERIAL, INC.; LONG, Alan; LEE, Hyoung, Ik; (185 pag.)WO2019/36407; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 14447-18-8, A common heterocyclic compound, 14447-18-8, name is Benzyl cyanoacetate, molecular formula is C10H9NO2, 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.

4b (0.30 g, 1.15 mmol) and 6a (0.24 g, 1.38 mmol) were dissolved in tetrahydrofuran (10 mL). Piperidine (11 muL, 0.11 mmol) was then dissolved and stirred at 50 C. for 10 hours. After the reaction was completed, the mixture was cooled at room temperature and extracted with ethyl acetate. The organic solvent layer was collected, and water was removed with magnesium sulfate, followed by concentration under reduced pressure. The resulting concentrate was purified by silica gel column chromatography (hexane: acetone: ethyl acetate = 3: 1: 1) to give compound 8a in 65% yield in the form of a purple powder.

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; Konkuk University Industry-Academic Cooperation Foundation; Jung, Yoo Hoon; Park, Kwang Soo; So, Yoo Jin; (14 pag.)KR101728909; (2017); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 160892-07-9, These common heterocyclic compound, 160892-07-9, name is 5-Bromoisophthalonitrile, 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.

The compound D (12.77 g, 17.86 mmol) and 5-bromoisophthalonitrile (3.20 g, 15.53 mmol) were completely dissolved in 210 ml of tetrahydrofuran in a 500 ml round-bottomed flask under nitrogen atmosphere, and 2M potassium carbonate aqueous solution (105 ml) And tetrakis(triphenylphosphine) palladium (0.54 g, 0.47 mmol) was added thereto, followed by heating and stirring for 3 hours.The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 120 ml of tetrahydrofuran to obtain Compound 9 (8.42 g, yield 76%).

Statistics shows that 5-Bromoisophthalonitrile is playing an increasingly important role. we look forward to future research findings about 160892-07-9.

Reference:
Patent; LG Chem, Ltd.; Cha Yong-beom; Kim Yeon-hwan; Jeon Sang-yeong; Cho Yeon-ho; Lee Seong-jae; Han Su-jin; (53 pag.)KR2019/44973; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts