Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 591769-05-0, name is 3-Cyclopentylacrylonitrile, 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 591769-05-0, category: nitriles-buliding-blocks

0.15g of compound 3 and 0.14g of compound 5a were dissolved in 30mL acetonitrile. To the above solution, 0.10g of 1,8-diazabicyclo undec-7-ene was added and reacted at 65¡ãC for 5-6 days. After distilling off the solvent, it was dissolved in ethyl acetate then water and aqueous citric acid solution was added. 100mL saturated sodium chloride solution was washed 3 times each. The organic phase was dried over anhydrous magnesium sulfate overnight. The mixture was filtered and the solvent was distilled off under reduced pressure to give a crude product. The product was purified by column chromatography (methylene chloride/methanol 80:1) to give 0.10g of intermediate 6a as a yellow solid, yield: 37percent.

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

Reference:
Patent; Shandong University; Zhang, Yingjie; Xu, Wenfang; Liang, Xuewu; (24 pag.)CN105418616; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 3939-09-1, The chemical industry reduces the impact on the environment during synthesis 3939-09-1, name is 2,4-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

To a solution of NaH (1.2 g, 30 mmol) in toluene (50 mL) was added but-3-en-1-ol (1.8 g, 25 mmol) dropwise and the mixture was allowed to stir at room temperature for 30 minutes. 2,4-Difluorobenzonitrile (4.2 g, 30 mmol) was then added in one portion and the mixture was allowed to stir at room temperature for 6 hours. Water (30 mL) was slowly added and the mixture was extracted with EtOAc and washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude residue was purified using flash column chromatography on silica gel (20:1 PE:EtOAc) to provide compound Int-2b (4.2 g, 78%) as a yellow oil. 1H NMR (400 MHz, CDCl3) delta 7.51-7.53 (m, 1H), 7.20-7.25 (m, 1H), 6.79-6.81 (m, 1H), 5.85-5.89 (m, 1H), 5.05-5.11 (m, 2H), 4.05-4.11 (m, 2H), 2.47-2.51 (m, 2H).

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, 2,4-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Reger, Thomas S.; Walji, Abbas M.; Sanders, John M.; Wai, John S.; Wang, Liping; US2015/203512; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 654-70-6, A common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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.

A. 4-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-2-trifluoromethyl-benzonitrile (453A) A mixture of 3-trifluoromethyl-4-cyano-aniline (24.0 g, 129 mmol) and maleic anhydride (14.0 g, 143 mmol) in 50 mL of acetic acid was heated at 115 C. overnight. A precipitate was obtained during the heating period. The reaction was allowed to stand at rt for an additional overnight period. The solid was removed by filtration, the filter cake was washed with diethyl ether and dried to give 21 g (79 mmol, 61%) of compound 753A as an off white solid. HPLC: 100% at 2.11 min (retention time) (YMC S5 ODS column, 4.6*50 mm, eluding with 10-90% aqueous methanol over 4 min containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

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; Salvati, Mark E.; Balog, James Aaron; Pickering, Dacia A.; Giese, Soren; Fura, Aberra; Li, Wenying; Patel, Ramesh N.; Hanson, Ronald L.; Mitt, Toomas; Roberge, Jacques Y.; Corte, James R.; Spergel, Steven H.; Rampulla, Richard A.; Misra, Raj N.; Xiao, Hai-Yun; US2004/77605; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

68119-31-3, name is 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile, 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. SDS of cas: 68119-31-3

(2,2-Difluoro-1,3-benzodioxol-5-yl)-acetonitrile (1.0 eq.), 50 wt% aqueous KOH (5.0 eq.), 1-bromo-2-chloro A mixture of ethane (1.5 eq.) and Oct 4 NBr (0.02 eq.) was heated at 70 C for 1 h. The reaction mixture was cooled and then treated with MTBE and water. The organic phase was washed with water and brine. The solvent was removed to provide (2,2-difluoro-1,3-benzodioxol-5-yl)-cyclopropanecarbonitrile.

The synthetic route of 68119-31-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; VERWIJS, MARINUS JACOBUS; ALARGOVA, ROSSITZA GUEORGUIEVA; KAUSHIK, RITU ROHIT; KADIYALA, IRINA NIKOLAEVNA; YOUNG, CHRISTOPHER; (118 pag.)TWI636051; (2018); B;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 876-31-3, The chemical industry reduces the impact on the environment during synthesis 876-31-3, name is 4-(Cyanomethyl)benzonitrile, I believe this compound will play a more active role in future production and life.

To a stirred and ice-cooled solution of sodium methoxide (0.388 g, 7.1802 mmol) in methanol (30 ml), 4-cyanophenylacetonitrile (0.817 g, 5.7442 mmol) and 1 – azido-2,4-dichloro-benzene (0.900 g, 4.7868 mmol) are added portion wise under a nitrogen atmosphere. The reaction mixture is allowed to attain room temperature spontaneously overnight, concentrated in vacuo, added water and extracted with ethylacetate (3 x 100 ml). The combined organic layers are dried over MgSO4, filtered and evaporated to give a dark brown gummy residue (1 .425 g, 90% mass balance). This crude material is purified by column chromatography over silica gel (230-400 mesh) eluting with 20% ethylacetate in petroleum ether, to afford the title compound as a yellow solid (0.450 g, 29% yield). LC-ESI-HRMS of [M+H]+ shows 330.0319 Da. CaIc. 330.031326 Da, dev. 1 .7 ppm.

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

Reference:
Patent; NeuroSearch A/S; WO2009/19278; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 1187-42-4, These common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, 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.

In a 100 mL two-necked flask, 2.6 lg (10 mmol) of 5-bromoacenaphthenequinone, 1.08 g (10 mmol) of diaminomaleonitrile, and 60 mL of acetic acid were sequentially added thereto, and the temperature was raised to 120 ¡ã C, and the mixture was stirred under reflux for 24 hours. The mixture was cooled to room temperature, poured into water, filtered under reduced pressure and washed with a large amount of water. The residue was dried and separated and purified on a silica gel column using dichloromethane: petroleum ether = 3:1 (volume ratio) eluent to obtain yellow. 3-bromoacenaphthenequinoneopyrazine-8,9-dicarbonitrile 2.44g, yield 77¡¤27percent

The synthetic route of 1187-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Soochow University (Suzhou); Liao Liangsheng; Yuan Yi; Jiang Zuoquan; Hu Yun; (37 pag.)CN108440424; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 5922-60-1, name is 2-Amino-5-chlorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-Amino-5-chlorobenzonitrile

Step 1 Methyl 4-chloro-2-cyanophenylcarbamate A 100 mL round bottom flask was charged with 2-amino-5-chlorobenzonitrile (0.76 g, 5.0 mmol), methyl chloroformate (0.43 mL, 5.40 mmol), NaHCO3 (0.5 g, 6.0 mmol) and 2-butanone (25 mL). The resulting mixture was stirred overnight at reflux. Reaction progress was monitored by TLC (EtOAc/Petroleum ether=1:10). Work-up: the reaction mixture was filtered and the solid was washed more 2-butanone (20 mL*2). The filtrate was concentrated in vacuo, to give 0.95 g (97percent) of the product as white solid.

The synthetic route of 5922-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kalypsys, Inc.; Alcon Research, Ltd; US2010/120741; (2010); 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. 134997-74-3, name is 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H6N2O2

To an ice cooled solution of the title compound from Step A above (5.6 g), di-tert-butyl dicarbonate (14.06 g) and NiCl2-OH2O (1.53 g) in MeOH, NaBH4 (8.51 g) was added in portions. The mixture was vigorously stirred for Ih at O0C and Ih at room temperature. After the addition of diethylenetriamine (3.5 mL) the mixture was concentrated, diluted with EtOAc, washed subsequently with IN HCl, saturated aqueous NaHCO3 and saturated aqueous NaCl, dried (MgSO4), concentrated to afford the title compound as an off-white solid (7.91 g, 88%). [M+Na]+ = 397.

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 134997-74-3.

Reference:
Patent; ALANTOS PHARMACEUTICALS HOLDING, INC.; WO2008/63667; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 64248-62-0,Some common heterocyclic compound, 64248-62-0, name is 3,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

3.6 mL (7.2 mmol) of trimethyl aluminum (2.0 M toluene solution) was dropwise added to a 10 mL of toluene containing 384 mg (7.17 mmol) of ammonium chloride at room temperature. After stirring for 1.5 hours, 1 g (7.1 mmol) of3,4-difluorobenzonitrile was added thereto and the resulting mixture was heated to EPO 85C for 9 hours. After completion of a reaction, the reaction solution was poured into100 mL of chloroform containing 200 g of silicagel and filtered off. The residue was washed with 200 mL of methanol and distillation was conducted to give 370 mg (2.36 mmol) of the title compound in a yield of 33%. [920] NMR: 1H-NMR(CD3OD) delta 7.87~7.82(1H, m), 7.72~7.7O(1H, m), 7.63~7.55(1H, m)[921] Mass(EI) 157(M++.)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Difluorobenzonitrile, its application will become more common.

Reference:
Patent; LG LIFE SCIENCES, LTD.; WO2006/104356; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

54202-05-0, name is Methyl 4-cyanobicyclo[2.2.2]octane-1-carboxylate, 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. HPLC of Formula: C11H15NO2

Methyl 4-cyanobicyclo[2.2.2]octane-l-carboxylate (0.83 g, 4.3 mmol) was taken up in methanol (86 mL), H2O (35 mL) and 1 N HCl (8.6 mL) along with PtO2 H2O (430 mg). The resulting reaction was stirred at room temperature under 35 psi of H2 for 5 h. TLC indicated that the reaction was complete (elution: petroleum ethcr/EtOAc=3:l , I2 visualization). The reaction mixture was concentrated under reduced pressure. Saturated aqueous Na2CO3 solution (20 mL) was then added, and the resulting mixture was extracted with CH2Cl2 (50 mLx2). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford methyl 4-(aminomethyl)bicyclo[2.2.2]octane- 1-carboxylate as an oil (0.76 g, yield: 89%). 1HNMR (400MHz, CD3OD) delta: 1.56 (6H, m), 1.85 (6H, m), 2.732 (2H, s), 3.654 (3H, s).

The synthetic route of 54202-05-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; WO2008/100423; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts