Month: September 2021

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,
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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

Electric Literature of 77326-36-4,Some common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, molecular formula is C7H5FN2, 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.

Sodium hydride (0.154 g, 3.85 mmol, 1.5 equiv) was added to a mixture of 2-amino-6-fluorobenzonitrile (0.524 g, 3.85 mmol, 1.5 equiv) and 2-methyl-2-((5-methylpyrimidin-2-yl)amino)propan-1-ol (Example 1b, 0.465 g,2.56 mmol, 1 equiv) in anhydrous THF (25 mL) under nitrogen. The reaction mixture was stirred for 10 minutes at room temperature and refluxed for 21 h. The reaction mixture was concentrated and the residue was purified by chromatography on a silica(50% EtOAc in Hexanes gradient) to provide the title compound (611 mg, 80% yield), MS 298 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-fluorobenzonitrile, its application will become more common.

Reference:
Patent; FIRMENICH INCORPORATED; FOTSING, Joseph, R.; TACHDJIAN, Catherine; SERVANT, Guy; CHING, Brett, Weylan; DAVIS, Timothy; (94 pag.)WO2020/33420; (2020); A1;,
Nitrile – Wikipedia,
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Reference of 2973-50-4, These common heterocyclic compound, 2973-50-4, name is 2-(2-Aminophenyl)acetonitrile, 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: In an Erlenmeyer flask, 2-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-yl)acetohydrazide (4) (1.0 mmol), aromatic nitriles (1.0 mmol) and DMAP (30 mol%) were taken in ethanol (15 mL). The reaction mixture was irradiated inside a synthetic microwave oven (Make-Ethosi Milestone with temperature control) for about 20-25 min (700 W). After completion of reaction (monitored by TLC), the mixture was concentrated to obtain the solid product. The solid product formed was filtered, dried and recrystallized from ethanol.

Statistics shows that 2-(2-Aminophenyl)acetonitrile is playing an increasingly important role. we look forward to future research findings about 2973-50-4.

Reference:
Article; Sangshetti, Jaiprakash N.; Kalam Khan, Firoz A.; Chouthe, Rashmi S.; Damale, Manoj G.; Shinde, Devanand B.; Chinese Chemical Letters; vol. 25; 7; (2014); p. 1033 – 1038;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 654-70-6 as follows. HPLC of Formula: C8H5F3N2

2-Isopropoxy-benzoyl chloride was condensed with 4-Amino-2-trifluromethyl benzonitrile in dichloromethane in presence of triethylamine as acid scavenger to yield N-4-Cyano-3-trifluoromethyl-phenyl)-2-Isopropoxy-benzamide. The reaction mixture was then concentrated in vacuo and the residue was extracted into ethyl acetate. The ethyl acetate layer was washed with water and with cold aqueous hydrochloric acid, then dried over sodium sulphate and finally concentrated in vacuo. The residue obtained was chromatographed over silica gel to afford the desired product. 1H-NMR:delta6.95-8.01 (7H,aromatic), delta4.04(1H,m,OCH), delta1.38(6H,d,Methyl)

According to the analysis of related databases, 654-70-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kundu, Tapas Kumar; Balasubramanyam, Karanam; Swaminathan, Vankatesh; US2006/167107; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 6621-59-6, name is 6-Bromohexanenitrile, 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 6621-59-6, Safety of 6-Bromohexanenitrile

General procedure: A solution of the corresponding precursor (4-chlorobutyronitrile for compounds 1, 5-chlorovaleronitrile for compounds 3 and 6-bromohexanenitrile for compounds 6) (2.5 mmol) in dimethylformamide (1 mL) was added during 1.5 h to a mixture of the arylamine (2.5 mmol), Cs2CO3(2.5 mmol) and KI (5 mmol) in dimethylformamide (2.5mL). The mixture was stirred at the indicated temperature and time. After completion of the reaction, as indicated by TLC, the mixture was treated with ethyl ether (50 mL) and water (10 mL). The aqueous phase was separated and extracted with ethyl ether (30 mL). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The solvent was evaporated in vacuo. The crude product was purified by column chromatography (silica gel, hexane:DCM).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromohexanenitrile, and friends who are interested can also refer to it.

Reference:
Article; Diaz, Jimena E.; Mollo, Maria C.; Orelli, Liliana R.; Beilstein Journal of Organic Chemistry; vol. 12; (2016); p. 2026 – 2031;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 53312-81-5, name is 5-Amino-2-fluorobenzonitrile, 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 53312-81-5, Safety of 5-Amino-2-fluorobenzonitrile

General procedure: To the solution of carboxylic acid (1 eq.) in DCM were added HATU (1.05 eq.), amine (1.1 eq.) and DIPEA (2 eq.). The mixture was stirred for 16 h at room temperature. Afterwards, the solution was washed with water and brine. The resulting organic layer was dried over MgSO4, and the solvent was removed by evaporation. The crude material was purified by flash chromatography (CH2Cl2:MeOH).

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, 5-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Egyed, Attila; Bajusz, David; Keser?, Gyoergy M.; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1497 – 1508;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 591769-05-0,Some common heterocyclic compound, 591769-05-0, name is 3-Cyclopentylacrylonitrile, molecular formula is C8H11N, 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.

To a solution of 4-(lH-pyrazol-4-yl)pynOlo[l,2-b]pyridazine-3-carbonitrile 16a (60 mg, 0.287 mmol) in DMF (1.5 mL) was added 3-cyclopentylacrylonitrile (109 mg, 0.717 mmol), 2,3,4,6,7,8,9, 10-octahydropyrimido[l,2-a]azepine (0.270 mL, 1.772 mmol) and heated with stirring at 50 °C for 3 h. The reaction mixture was cooled to RT and concentrated in vacuum to dryness. The residue obtained was purified by combiflash column chromatography [silica gel, 4 g eluting with hexanes/ethyl acetate (1 :0 to 2:1)] to give 4-(l-(2-cyano-l-cyclopentylethyl)-lH- pyrazol-4-yl)pyrrolo[l,2-b]pyridazine-3-carbonitrile 16b (56 mg, 59percent, Rf = 0.42 with hexanes/ethyl acetate = 2:1) as a yellow solid; 1H NMR (300 MHz, OMSO-d6) delta 8.80 (d, J= 0.6 Hz, 1H), 8.48 (s, 1H), 8.31 (s, 1H), 8.19 (t, J= 2.1 Hz, 1H), 7.13 (d, J= 2.0 Hz, 2H), 4.64 (td, J = 9.0, 4.8 Hz, 1H), 3.29 – 3.21 (m, 2H), 2.48 – 2.37 (m, 1H), 1.91 – 1.11 (m, 8H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Cyclopentylacrylonitrile, its application will become more common.

Reference:
Patent; BIOCRYST PHARMACEUTICALS, INC.; BABU, Yarlagadda, S.; KOTIAN, Pravin, L.; WU, Minwan; WO2011/150356; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts