Author: Jessica.F

Adding a certain compound to certain chemical reactions, such as: 2032-34-0, name is 3,3-Diethoxypropanenitrile, 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 2032-34-0, Quality Control of 3,3-Diethoxypropanenitrile

Step 1. l-cyclopropyl-lH-pyrazol-5-amine [0634] A 100-mL round-bottom flask was charged with 3,3-diethoxypropanenitrile (0.600 g, 4.19 mmol), cyclopropylhydrazine di-hydrochloride (0.610 g, 4.21 mmol) and ethanol (20 mL), and the resulting solution stirred for 18 h at 80 C. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 10: 1, dichloromethane/methanol) to afford l-cyclopropyl-lH-pyrazol-5-amine (0.206 g, 36% ) as light yellow oil. MS (ESI, pos. ion) m/z 124[M+H]+.

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; BAIR, Kenneth W.; HERBERTZ, Torsten; KAUFFMAN, Goss Stryker; KAYSER-BRICKER, Katherine J.; LUKE, George P.; MARTIN, Matthew W.; MILLAN, David S.; SCHILLER, Shawn E. R.; TALBOT, Adam C.; WO2015/74064; (2015); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 57381-37-0, These common heterocyclic compound, 57381-37-0, name is 2-Bromo-5-chlorobenzonitrile, 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.

GammaAlpha1 l-(2-Bromo-5-chloro-phenyl)cvclopropanamine To a stirred solution of 2-bromo-5-chlorobenzonitrile (10 g, 46 mmol) and Ti(Oi-Pr)4 (16.64 mL, 55 mmol) in THF (200 mL) at -78C was added EtMgBr (138 mL, 138 mmol) drop wise. The reaction mixture was allowed to warm up to room temperature and stirred for 2 hours. BF3-Et20 (17.2 mL) was added, and the solution was stirred for another 16 hours before it was quenched with aq. HCl solution and washed with EtOAc. The aqueous phase was adjusted to pH – 10 with aq. NaOH solution, and exacted with EtOAc three times. The combined organic layers were concentrated to give a crude product which was purified by silica gel flash chromatography to afford title compound (2 g, 17.6%). MS: 246.7 (M+H+, 1C1) as oil.

The synthetic route of 57381-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt E.; CHEN, Junli; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; LI, Dongbo; MAERKI, Hans Peter; MARTIN, Rainer E.; MAYWEG, Alexander; TAN, Xuefei; WU, Jun; YU, Jianhua; (109 pag.)WO2016/55394; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 13544-06-4, 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 13544-06-4 as follows.

Step 1. Preparation of 2-Methyl-2-(2-nitro-4- trifluoromethyl-phenyl) -propionitrile; The title compound was synthesized according to a method described in Prasad, G. , J. Org. Chem. 1991,56, 7188-7190. To a yellow-brown solution of (2-Nitro-4-trifluoromethyl- phenyl) -acetonitrile (2.5 g, 11 mmol), 18-crown-6 (0.72 g, 2.7 mmol), and methyl iodide (1.5 mL, 24 mmol) in dry THF under nitrogen at-78 degrees C was added potassium tert- butoxide (2.7 g, 24 mmol) in one portion. The reaction immediately became a deep purple color. The reaction was allowed to stir for 2 h at-78 degrees C, and was then warmed to ambient temperature. A water-cooled reflux condenser was added and the solution heated to 70 degrees C under nitrogen. Over 40 minutes, the color changed from dark purple to cloudy gray. The mixture was allowed to cool to room temperature, and was concentrated in vacuo. The resulting material was partitioned between 1 N HCI and EtOAc. The organic layer was washed once with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give a brown oil which was judged to be primarily monoalkylated nitrile. The crude material was resubjected to the reaction conditions using 18-crown-6 (0.72 mg, 2.7 mmol), methyl iodide (0.75 mL, 12 mmol), and potassium tert- butoxide (1.4 g, 12 mmol) as before, with the following modifications: the reaction was allowed to stir only 10 min. at-78 degrees C before being warmed to room temperature, and the reaction vessel was sealed and heated to 70 degrees C for 2 h. Upon cooling to room temperature, the reaction was quenched and worked up as before. Purification by flash chromatography afforded the desired product as a light brown solid. MS (M+H) + = 259; Calc’d 258.20 for C11H9F3N2O2.

According to the analysis of related databases, 13544-06-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2005/113494; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 115279-57-7, 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. 115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate (6.4 g, 23.6 mmol) and 2-(4-aminophenyl)-2-methylpropionitrile (5.6 g, 35 mmol) were dissolved in tert-butanol (200 mL), to the system added potassium carbonate (16.4 g, 119 mmol), and the reaction mixture was stirred under reflux for 2 h. After confirming a disappearance of the raw materials by a thin layer chromatography plate (ethyl acetate:petroleum ether=1:3), the reaction mixture was suction filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was washed with diethyl ether to give 8.1 g of a pale yellow solid.

The synthetic route of 2-(4-Aminophenyl)-2-methylpropanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XUANZHU PHARMA CO., LTD.; Wu, Frank; Zhang, Yan; US2015/166539; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 3215-64-3, name is 2-(2,6-Dichlorophenyl)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 3215-64-3, Quality Control of 2-(2,6-Dichlorophenyl)acetonitrile

4-amino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (l-2a) (3.1 g, 18 mmol) was dissolved in 40 rtiL anhydrous dimethylformamide and cooled in an ice/methanol bath (-10 C) for 15 minutes under an atmosphere of nitrogen. Sodium hydride (0.73 g, 18 mmol) divided into 5 portions was added over the course of 5 minutes keeping the reaction mixture cooled with stirring. After an additional 5 minutes, a solution of 2,6-dichlorobenzylacetonitrile (1-la) (4.9 g, 27 mmol) in 12 mL anhydrous dimethylformamide was added drop wise via syringe. The resulting mixture was stirred at -10 C for 30 minutes then allowed to warm to room temperature overnight after which time the reaction mixture was cooled in an ice bath and slowly quenched with 50 mL saturated NEUCl. After stirring for 20 minutes the product was extracted into DCM. The combined DCM extracts were dried over MgSCk, filtered, and concentrated under reduced pressure. The residue was re-dissolved in ethyl acetate and washed with brine. The organic layer was filtered through a sintered glass funnel and the filtrate was dried over sodium sulfate, filtered, and concentrated under reduced pressure to dryness. The residue was purified by silica gel chromatography eluting with ethyl acetate/dichloromethane to afford 708 mg (11%) 6-(2,6- dichlorophenyl)-2-methylsulfanyl-pyrido[2,3-d]pyrimidin-7-amine (l-3a). LCMS (ESI):[M+H]? = 336.9

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2,6-Dichlorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; ACHAOGEN, INC.; COHEN, Frederick; KANE, Timothy Robert; DOZZO, Paola; HILDEBRANDT, Darin James; LINSELL, Martin Sheringham; MACHAJEWSKI, Timothy D.; MCENROE, Glenn A.; (172 pag.)WO2018/23081; (2018); 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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-(3-Nitrophenyl)acetonitrile

To a solution of 3-nitro-phenyl-acetonitrile (3.20 g, 19.7 mmol) in MeOH(50 mL) was added Pd/C (10% wt, -50% H20, 0.32 g) and the mixture was placed under H2 (80 psi) and stirred for 2 days at 22 0C. The reaction mixture was filtered through Celite and the filtrate concentrated in vacuo to give crude product as a yellow oil. The residue was purified by silica gel chromatography (ISCO, elution with 0-10% ethyl acetate in hexanes) to give xix-1-1 (1.15 g, 44%): MS m/z = 133 (M-H).

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 621-50-1.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2006/41773; (2006); A2;,
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. 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

Experiment 38. A range of experiments were conducted examining the resolution of diol with (+)- (S,S)-DTT. The general procedure is described below, and the details and results for each reaction are in table 1.Racemic diol (20 g, 58.4 mmol) was dissolved in approximately half of the solvent used for the experiment at 40 0C. (-H)-(S5S)-DTT-H2O (quantity specified in the table) was added as a solution in the other half of the solvent. The solution was held at 40 0C and was seeded within two minutes with crystals of (S)-diol. ./2(-H)-(S5S)-DTT (approximately 5 mg). Crystallisation typically began within 5-10 minutes after seeding. After 2 h at 40 0C, the temperature of the solution was lowered to 20 0C over 2 h, and the solution was held at this temperature for a further 1 h. The product was then separated by filtration, washed with the approriate solvent (2 x 20 mL) and dried overnight at 60 0C under reduced pressure.

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; H. LUNDBECK A/S; WO2009/33488; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 57381-51-8, 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. 57381-51-8, name is 4-Chloro-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(a) 4-Chloro-2-fluoro-5-nitrobenzonitrileA mixture of 4-chloro-2-fluorobenzonitrile (4.62 g; 29.7 mmol) in cone. H2S04 (42 mL) was treated dropwise with cone. HN03 (3.9 mL) at 1-2 C. After stirring at 1-2 C for 2 h the mixture was poured into ice and filtered.Yield: 5.18 g (87%).

The synthetic route of 4-Chloro-2-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; PRIEPKE, Henning; KUELZER, Raimund; MACK, Juergen; PFAU, Roland; STENKAMP, Dirk; PELCMAN, Benjamin; ROENN, Robert; LUBRIKS, Dimitrijs; SUNA, Edgars; WO2012/76672; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 874-90-8, These common heterocyclic compound, 874-90-8, name is 4-Methoxybenzonitrile, 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.

Bis(4-methoxyphenyl)methammine (1) was prepared according to the procedure described in Pickert et al., (1973) Organic Syntheses Coll. Fpp520-522 and Dejaegher et al., (2002) Synlett 113-115. Magnesium (0.76 g) was suspended in 30 mL dry THF in a flame-dried 3-neck round-bottomed flask equipped with a stir bar. Some drops of 4-bromoanisole were added, and to initiate the reaction, a crystal of iodine was added and the solution heated to a gentle reflux (-6O0C). Once the color of the iodine had disappeared, the remaining l-bromo-4- methoxybenzene (3.9 mL) in 8 mL THF was added. The mixture was refluxed for 45 minutes. After cooling to RT, 2.5 g of p-methoxybenzonitrile in dry THF was added over 20 minutes and reacted for 6 h under reflux. The reaction mixture was cooled and 4.5 mL of methanol added to quench the reaction. After stirring for 20 minutes, it was concentrated to remove THF, redissolved in CH2Cl2 and quickly washed with water in a separatory funnel to remove Mg salts. The CH2Cl2 layer was dried over MgSO4, concentrated, redissolved in a minimal amount of dichloromethane and diethyl ether added to precipitate white shiny crystals of Bis(4- methoxyphenyl)methanimine (4.01 g, 59% yield). It is worthy of mention that the preparation of this diarylketimine was simple and efficient resulting in crystals without any additional lengthy purification steps such as distillation or chromatography which contributes to the simpler glycosylation chemistry. Rf = 0.32 (60% EtOAc: hexanes), m.p. = 128-129 0C, 1H NMR (CDCl3, 500 MHz) d 3.84 (6H, s), 6.90 (4H, d, J= 9.0 Hz), 7.52 (4H, d, J= 8.5 Hz), 8.95 (NH, broad) ; 13C NMR (CDCl3, 500 MHz) d 55.3 (2CH3O), 113.4 (4CH), 129.98 (4CH), 132.1(2C, q), 161.1 (2C- O, q), and 176.9 (C=N).

Statistics shows that 4-Methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 874-90-8.

Reference:
Patent; THE ARIZONA BOARD OF REGENTS ON BEHALF OF THE UNIVERSITY OF ARIZONA; WO2007/55698; (2007); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 872091-83-3, name is Methyl 4-chloro-3-(cyanomethyl)benzoate, 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 872091-83-3, Application In Synthesis of Methyl 4-chloro-3-(cyanomethyl)benzoate

Add gaseous anhydrous hydrochloric acid for 3 h at 0 C. to a solution of 19.68 g of 4-chloro-3-cyanomethyl-methyl benzoate in 207 ml of methanol.Stir the reaction mixture for 16 h at room temperature, then concentrate at reduced pressure. Take up the residue in 600 ml of ethyl acetate and 500 ml of water. Wash the organic phase with 200 ml of an aqueous solution of sodium chloride, dry over sodium sulphate and concentrate at reduced pressure.The expected product is obtained in the form of crystals.m.p.=55 C.

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, Methyl 4-chloro-3-(cyanomethyl)benzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SANOFI-AVENTIS; US2010/69384; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts