Month: July 2021

Reference of 21803-75-8, 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. 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Compound 3b (390.0 g, 1.00 mol) was dissolved in 800 mL 2-Me-THF followed by the addition of triethylamine (TEA, 232.5 g, 2.30 mol). The light yellow solution was cooled to 5 C. Methanesulfonyl chloride (126.0 g, 1.10 mol) was added within 1 h while maintaining the temperature at 5 C. The reaction was continued for 1 h at 5 C. A solution of 4b (4-amino-3- chlorobenzonitrile) (167.0 g, 1.10 mol) in 300 mL 2-Me-THF was added and the slurry was heated to reflux (-84 C), followed by stirring under reflux for 4 h. The reaction mixture was cooled to 20 C and the precipitate was removed by suction filtration. The product cake was washed with 200 mL 2-Me-THF. The mother liquor was used as such in the next step.

The chemical industry reduces the impact on the environment during synthesis 4-Amino-3-chlorobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; INTERVET INTERNATIONAL B.V.; BRINK, Monika; NIEDERMANN, Hans-Peter; KNELL, Marcus; FENG, Tao; TRZASKA, Scott, T.; COOPER, Arthur, J.; DESAI, Shaileshkumar Ramanlal; GORE, Vinayak Keshav; WO2012/85645; (2012); 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. 78881-21-7, name is 4-Amino-3-methylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

A mixture of 6-chloro-4-isopropyl-N- (tetrahydro-pyran-4-ylmethyl)-nicotinamide (Description 24) (100mg), 4-amino-3-methyl benzonitrile (2eq), cesium carbonate (168mg), tris (dibenzylideneacetone) palladium (0) (Pd2 (dba) 3) (3.4mg), 4,5-bis (diphenylphosphino)-9, 9- dimethylxanthene (Xantphos) (2.3mg) in 1, 4-dioxane (lml) was irradiated under microwave conditions at 150C for 30 minutes. Further quantities of cesium carbonate (168mg), Pd2 (dba) 3 (3.4mg) and Xantphos (2.3mg) were added and the mixture was again subjected to microwave conditions at 150C for 30 minutes. Ethyl acetate was added and the mixture was washed with water. The ethyl acetate layer was dried (sodium sulphate) and the solvent was removed under reduced pressure. The residue was purified using MDAP to give the title compound (20mg) NMR (MeOD) 8 1.25 (6H, d), 1.29-1. 43 (2H, m), 1. 70 (2H, d), 1.81-1. 93 (1H, m), 2.3393H, s), 3. 2 1- 3.50 (5H, m), 3.98 (2H, dd), 7.01 (1H, s), 7.49 (1H, dd), 7.55 (1H, bs), 8.02 (1H, d), 8.09 (1H, s) LC/MS, t = 2.89 min, Molecular ion observed [MH+] = 393 consistent with the molecular formula C23H28N402

According to the analysis of related databases, 78881-21-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; DOUGHTY, Jennifer, Margaret; WO2005/74939; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 654-70-6, These common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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.

10-Chloro-2-cyclopentyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-5-one (Intermediate 1, 157 mg, 0.56 mmol), 4-amino-2-methyl-benzonitrile (Aldrich, 95 mg, 0.51 mmol) and 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene (27 mg, 0.05 mmol) were dissolved in 1,4-dioxane (7.5 mL). Caesium carbonate (330 mg, 1.01 mmol) was added and the mixture purged with a stream of nitrogen for 5 minutes. Tris(dibenzylideneacetone) palladium (II) (28 mg, 0.03 mmol) was added and the apparatus was evacuated and backfilled with nitrogen (×3) and then heated at 100 C. for 8 h. The mixture was cooled, filtered and the filtrate absorbed onto an SCX-3 column, washed with methanol and the product eluted with ammonia in methanol. Product containing fractions were concentrated and purified by preparative reverse phase chromatography to give the title compound as a white solid. (21 mg, 10%)1H NMR (399.9 MHz, DMSO-d6) delta1.57-1.72 (6H, m), 1.92-2.00 (2H, m), 2.61 (2H, m), 3.19 (3H, s), 3.64-3.66 (2H, m), 4.82-4.90 (1H, m), 7.99-8.07 (2H, m), 8.16 (1H, s), 8.50 (1H, d), 10.15 (1H, s); MS m/z 431 [M+H]+.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; US2008/9482; (2008); A1;,
Nitrile – Wikipedia,
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Electric Literature of 4426-11-3,Some common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, molecular formula is C5H7N, 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.

S nthesis of l-(5-bromo-pyridin-2-yl)-cyclobutanecarbonitrileTo a solution of lithium diisopropylamine (2.0 M in heptane/THF/ethylbenzene, 10 mL, 20.0 mmol) at -78 C is added R-4 (811 mg, 10.0 mmol). The reaction mixture is stirred at -78 C for 45 minutes, followed by the addition of R-3 (1.9 g, 8.0 mmol). The reaction mixture is allowed to warm to room temperature slowly, stirred for 16 hours, and heated at 70 C for 2 hours. The reaction mixture is allowed to cool to room temperature, and partitioned between EtOAc and H20. The combined organics are washed with brine, dried with Mg2S04, filtered, and concentrated in vacuo. The residue is purified by flash chromatography (Si02, 0-100% EtOAc in heptane) to give the title intermediate 1-13

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; BERRY, Angela; CHEN, Zhidong; DE LOMBAERT, Stephane; EMMANUEL, Michel Jose; LOKE, Pui Leng; MAN, Chuk Chui; MORWICK, Tina Marie; TAKAHASHI, Hidenori; WO2012/82817; (2012); A1;,
Nitrile – Wikipedia,
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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. 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-(4-Fluorophenyl)-3-oxopropanenitrile

100 mL flask into a commercially available chemicals of p-fluorobenzoylacetonitrile(1) (3.2898 g, 20.16 mmol) was and suspensions put a polyphosphoric acid (20mL). This in acetone (2.4177 g, 41.63 mmol) was added and stirred for 30minutes at 80 to 90 C, and stirred for 30minutes from 140 to 150 C agitated at 30 minutes. Ice is poured into a beaker filled with a reactionliquid (100 ml), sodium carbonate powder is added carefully and neutralizedwith chloroform extracts 4 times, after drying with anhydrous sodium sulfate,distillation, solvent. Residue obtained from the recrystallization and ethylacetate, compd. 2a (2. 2037 g, 10. 84 mmol, 54%) is obtained.

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 4640-67-9.

Reference:
Patent; SHIONOGI & COMPANY LIMITED; SUZUKI, HIDEYUKI; (33 pag.)JP2016/700; (2016); A;,
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Some common heterocyclic compound, 14346-13-5, name is 2,5-Diaminobenzonitrile, molecular formula is C7H7N3, 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. Formula: C7H7N3

A solution of (S)-N-[1-(2-chloro-6-propylpyrimidin-4-yl)pyrrolidin-3-yl]acetamide (20 mg, 0.08 mmol) prepared in Preparation 13 and 2,5-diaminobenzonitrile (9.5 mg, 0.07 mmol) prepared in Preparation 19 in n-butanol (0.5 ml) was reacted in a microwave reactor (450 W) for 40 minutes. The reaction mixture was cooled to room temperature and then filtered to give 17.1 mg of the product as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14346-13-5, its application will become more common.

Reference:
Patent; YUHAN CORPORATION; Lee, Hyun-Joo; Kim, Dong-Hoon; Kim, Tae-Kyun; Yoon, Young-Ae; Sim, Jae-Young; Cha, Myung-Hun; Jung, Eun-Jung; Ahn, Kyoung-Kyu; Lee, Tai-Au; US2013/338179; (2013); A1;,
Nitrile – Wikipedia,
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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. 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 63069-50-1

A mixture of 4-amino-3-fluorobenzonitrile (5.0 g, 36.76 mmol) and p-toluenesulfonic acid (20.0 g, 105.2 mmol) in acetonitrile (50 mL) was stirred at RT for 4 h. Then aq. solution of NaNO2 (3.8 g, 55.07 mmol) and KI (9.15 g, 55.07 mmol) were added at 0C and stirred further for lh. After the reaction completion, the reaction mixture was quenched with water, washed with an aqueous solution of NaHSO3 and extracted with EtOAc. The organic layerwas washed with water, brine, dried over Na2SO4 and concentrated to afford 4.0 g of the title product. ?H NMR (300 MHz, CDC13): 7.94-7.89 (t, J = 8.4 Hz, 1H), 7.34-7.32 (d, J = 7.5 Hz, 1H), 7.21-7.19 (d, J= 8.1 Hz, 1H).

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; GLENMARK PHARMACEUTICALS S.A.; GHARAT, Laxmikant Atmaram; MUTHUKAMAN, Nagarajan; PISAL, Dnyandeo; KHAIRATKAR-JOSHI, Neelima; SHAH, Daisy Manish; KADAM, Sheetal R; (303 pag.)WO2016/55947; (2016); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 3544-25-0, name is 2-(4-Aminophenyl)acetonitrile, 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 3544-25-0, Computed Properties of C8H8N2

A solution of sodium nitrite (3.15 g, 45.7 mmol) in water (20 mL) was added dropwise to a cooled (-15 C.), stirred suspension of 4-aminobenzonitrile (5 g, 42.3 mmol) in a concentrated hydrogen chloride solution (55 mL) at such a rate as to maintain a temperature below -10 C. After the addition was finished, the reaction mixture was quickly filtered to remove solids, and the filtrate was added in portions to a cooled (-20 C.), stirred solution of SnCl2.2H2O (47.7 g, 0.21 mol) in a concentrated hydrogen chloride solution (37 mL) at such a rate as to keep the temperature below -10 C. After stirring the solution for an additional 15 minutes, the solid was collected, washed with diethyl ether (4*25 mL), and dried to give (4-hydrazinophenyl)acetonitrile hydrochloride (5.6 g, 78%).

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

Reference:
Patent; The Ohio State University Research Foundation; US2009/111799; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 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 1080-74-6, Quality Control of 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile

4) Compound 3 (0.203 g, 0.18 mmol),1,1-dicyanomethylidene-3-indanone (INCN) (0.35 g, 1.8 mmol),Pyridine (1 mL was dissolved in a single-mouth bottle containing 30 mL of chloroform,The mixture was stirred under reflux at 65 C overnight under Ar protection, and the reaction was cooled to room temperature.DCM extraction, the crude product was purified on a silica gel column.A blue solid (BIC) was obtained. (0.159 g, 60%).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Central South University; Zou Yingping; Luo Mei; Yuan Jun; Zhou Liuyang; Cai Fangfang; Jiang Wenhui; (21 pag.)CN108948042; (2018); 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. 14618-78-1, name is 4,4-Dimethoxybutanenitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H11NO2

To a solution of diisopropylamine (4.77 mL, 34.1 mmol, 2.2 equiv) in THF (50 mL) at -10Cunder N2 was added 1.5 M n-BuLi in hexanes (22.7 mL, 34.1 mmol, 2.2 equiv). After 30 mm the mixturewas cooled to -78 C and a solution of nitrile (2.0 g, 15.5 mmol, 1.0 equiv) in THF (10 mL) was added.After 1 h iodomethane (2.12 mL, 34.1 mmol, 2.2 equiv) was added. The mixture was slowly warmed to 0C and kept there for 14 h, at which time it was quenched with sat. aq. NH4C1 (40 mL) and extracted withEtOAc (3 x 20 mL). The organics were dried over Na2SO4, filtered and concentrated in vacuo. Theresultant oil was purified by flash chromatography on silica gel (5:1 -3:1 hexanes/EtOAc) to yield theproduct (2.105 g, 87%) as a yellow oil. R1= 0.49 (3:1 hexanes/EtOAc). ?HNMR(400 MHz, CDC13) 3:4.60 (t, 1H, J= 5.6 Hz), 3.37 (s, 6H), 1.83 (d, 2H, J= 4.4 Hz), 1.39 (s, 6H); ?3C NMR (100 MHz, CDC13)3: 124.7, 102.4, 53.3, 43.0, 30.0, 27.5

The synthetic route of 14618-78-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; SALK INSTITUTE FOR BIOLOGICAL STUDIES; PACHE, Lars; CHANDA, Sumit, K.; VAMOS, Mitchell, Dennis; COSFORD, Nicholas David, Peter; TERIETE, Peter; MARLETT, John; DIAZ, Arturo; YOUNG, John, A.T.; WO2015/187998; (2015); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts