Category: nitriles-buliding-blocks

Application of 658-99-1,Some common heterocyclic compound, 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile, molecular formula is C8H5F2N, 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 51 -(4-(5-(2-( 1 -(3 ,4-difluorophenyl)cyclohexyl)ethyl)- 1 ,2,4-oxadiazol-3 – yl)benzyl)azetidine-3-carboxylic acidPreparation 5 A: l-(3,4-difluorophenyl)cyclohexanecarbonitrile [0136] To a solution of 2-(3,4-difluorophenyl)acetonitrile (2 g, 13.06 mmol) in 20 mL of DMF at 0C was added 60% sodium hydride (1.149 g, 28.7 mmol), and the mixture was stirred at the same temperature for 5 mins. Then a solution of 1,5-dibromopentane (1.779 mL, 13.06 mmol) in 20 mL of DMF was added dropwise and the mixture was stirred at a temperature in the range 0C to room temperature for 5 hrs. The reaction was quenched with water, and extracted with EtOAc. The mixture was washed with water and brine. The combined aqueous layers were back extracted with EtOAc once and washed with brine. The combined extracts were dried over a2S04 and evaporated to give an oily residue. It was purified by Combiflash (120g silica gel) eluting with 1 :9 EtOAc-hexane to give l-(3,4-difluorophenyl) cyclohexanecarbonitrile (2.52 g, 1 1.39 mmol, 87 % yield). lH NMR (400 MHz, CC13D) delta ppm 7.12-7.35 (3 H, m), 2.14 (2 H, d, J= 11.86 Hz), 1.75-1.95 (6 H, m), 1.64-1.75 (2 H, m)

The synthetic route of 658-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; DAS, Jagabandhu; KO, Soo Sung; SRIVASTAVA, Anurag; MOQUIN, Robert V.; WATTERSON, Scott H.; WO2012/12477; (2012); A1;,
Nitrile – Wikipedia,
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Application of 67832-11-5,Some common heterocyclic compound, 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, molecular formula is C8H6BrN, 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 164A 4′-methoxy-3-methyl-1,1′-biphenyl-4-carbonitrile 4-Bromo-2-methylbenzonitrile (4.9 g, 25.0 mmol), Pd(PPh3)4 (578 mg) in benzene (50 mL) and 2.0 M aqueous solution of Na2CO3 (25 mL, 50.0 mmol) was treated with 4-methoxyphenylboronic acid (4.56 g, 30.0 mmol) in ethanol (20 mL) and heated at 75 C. for 17 hours. The mixture was allowed to cool to room temperature and the phases were separated. The aqueous phase was extracted with diethyl ether (3*40 mL). The original benzene layer and the diethyl ether extracts were combined, filtered over celite, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography over silica using a mixture of hexane/CH2Cl2 (3:1) to provide the title compound as a white powder (5.73 g, 85% yield). 1H-NMR (300 MHz, CDCl3) delta2.35 (3H), 3.70 (s, 3H), 6.80-7.50 (m, 7H); MS (DCI) m/z 224 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-methylbenzonitrile, its application will become more common.

Reference:
Patent; Abbott Laboratories; US6620839; (2003); B2;,
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. 4714-62-9, name is 4-(Methylamino)benzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C8H8N2

A mixture of the compound (450 mg) obtained in Step 1, 90% sodium azide (664 mg), triethylammonium chloride (703 mg) and anhydrous 1-methyl-2-pirrolidone (12 mL) was stirred at 140 to 160C for ten hours under nitrogen atmosphere. The reaction mixture was poured into ice-water, and the residue was adjusted to pH 3 with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was crystallized from tert-butyl methyl ether, collected by filtration and dried to obtain the titled compound (471 mg) as crystals.

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; MOCHIDA PHARMACEUTICAL CO., LTD.; EP1391452; (2004); 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. 127666-99-3, name is 2-Chloro-4-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H6ClNO

A mixture of tris(dibenzylideneacetone)dipalladium (33 mg, 0.0357 mmol) and tricyclohexylphosphine (47 mg, 0167 mmol) in anhydrous dioxane (2.5 mL) was stirred for 30 min at room temperature under an atmosphere of argon. 4,4,4′,4′,5,5,5′,5′-Octamethyl- 2,2′-bi-l,3,2-dioxaborolane (333 mg, 1.31 mmol) potassium acetate (175 mg, 1.785 mmol) and a solution of 2-chloro-4-methoxybenzonitrile (200 mg, 1.19 mmol) in anhydrous dioxane (2.5 mL) were sequentially added and the resulting mixture was irradiated in a microwave at 120 0C for 15 h. Concentration of the reaction mixture and purification by column chromatography, using a gradient of 0-30 % ethyl acetate in heptane as the eluent, gave 238 mg (77% yield) of the title compound: 1H NMR (CDCl3) delta 7.63 (d, J= 8.6 Hz, 1 H)3 7.35 (d, J= 2.8 Hz3 1 H)3 7.01 (dd3 J= 8.63 2.8 Hz, 1 H)3 3.88 (s, 3 H)3 1.39 (s, 12 H); MS (EI) m/z

According to the analysis of related databases, 127666-99-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; ASTEX THERAPEUTICS LTD; WO2008/76046; (2008); A1;,
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. 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

N1 4-(2-Benzyloxyethyl)benzonitrile This compound was prepared by alkylation of 4-(2-hydroxyethyl)benzonitrile with benzyl bromide in the presence of sodium hydride in THF initially at 0 C. and then at ambient temperature.

The synthetic route of 69395-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KNOLL Aktiengesellschaft; US5780642; (1998); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 64248-62-0, 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 64248-62-0 as follows.

Into the 500 ml reaction flask, place 40 g (R)-2-(4-hydroxyphenoxy)propionic acid and 0.5 g ammonium bromide, and add 100 ml dimethyl formamide DMF and 50 ml toluene as solvent to dissolve it. After slowly adding potassium carbonate 70.7 g. After waiting for the reaction flask to not generate gas, add 30.5 g bromobutane. After 85 C reaction 7 hours, add 31 g 3,4-difluorobenzonitrile react for 5 h, then filtered and the filtrate, and 50 ml toluene after washing with the filtrate after the merger of the desolvation, drying the obtained cyhalofop 75.2 g, total reaction yield is 95.7%, the appearance is a white solid.

According to the analysis of related databases, 64248-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Jiangsu Yongkai Chemical Co., Ltd.; Jiang Yunxiang; Zhao Feisi; Dong Haitao; Chen Kuanxin; Wei Dongyu; (7 pag.)CN107253912; (2017); A;,
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. 120351-94-2, name is 3-(2-Aminoethoxy)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H10N2O

Step 4 Synthesis of N-[2-(3-cyanophenoxy)ethyl]-4-cyanobenzamide: 1.13 g (7.68 mmol) of 4-cyanobenzoic acid and 1.6 ml (14.1 mmol) of N-methylmorpholine were dissolved in 30 ml of dimethylformamide. 0.67 ml (7.05 mmol) of ethyl chloroformate was added to the solution under cooling with ice/water. After stirring for 5 minutes, 1.27 g (6.41 mmol) of 3-(2-aminoethoxy)benzonitrile was added to the reaction mixture, and the obtained mixture was stirred at room temperature for one hour. After the treatment with ethyl acetate as the extractant in an ordinary manner, the title compound was obtained. Yield: 1.29 g (4.43 mmol) (69 %). MS (FAB, m/z) 292 (MH+) H-NMR (CDCl3) delta 3.91 (2H, dt), 4.19 (2H, t), 6.78 (1H, br), 7.14 (1H, d), 7.17 (1H, s), 7.28 (1H, d), 7.39 (1H, t), 7.75 (2H, d), 7.90 (2H, d)

According to the analysis of related databases, 120351-94-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ajinomoto Co., Inc.; EP976722; (2000); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 3598-14-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 3598-14-9 name is Phenoxyacetonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a stirred suspension of corresponding nitrile and hydroxylamine hydrochloride (1.5 equiv.) in EtOH (10 mL per gram of nitrile) a NaHCO3 (1.5 equiv.) was added. The reaction mixture was stirred under reflux for a 6 h. After the reaction had completed, the reaction mixture was concentrated under reduced pressure, and the residue was diluted with cold water (200 mL). The resulting precipitate was filtered off and washed with cold water (50 mL).

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

Reference:
Article; Presnukhina, Sofia; Tarasenko, Marina; Baykov, Sergey; Smirnov, Sergey N.; Boyarskiy, Vadim P.; Shetnev, Anton; Korsakov, Mikhail K.; Tetrahedron Letters; vol. 61; 9; (2020);,
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. 144649-99-0, name is 5-Bromo-2-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H6BrNO

16.23 ml of n-butyllithium solution (1.6M in hexane) are added dropwise to a solution of 5.00 g of 5-bromo-2-methoxybenzonitrile in 90 ml of dry tetrahydrofuran at -78C. After stirring at this temperature for 45 minutes, 6.71 ml of triisopropylborate are added, and the mixture is then slowly warmed to -20C. 50 ml of 1 N HCl are added to the reaction mixture. The phase is separated and the aqueous phase is extracted three more times with 100 ml of diethyl ether each time. The combined organic phases are dried with sodium sulphate, filtered and evaporated. The remaining oil is mixed with pentane, and the precipitate which separates out is filtered off with suction and washed once with a little dichloromethane. Drying under high vacuum affords the title compound as a white solid. Rt = 2.74.

According to the analysis of related databases, 144649-99-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Speedel Experimenta AG; EP1987834; (2008); A2;,
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. 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 499983-13-0

Step 6: Preparation of 1 -(4-bromo-3-fluorophenyl)cyclopropanecarbonitrile; To a room temperature solution of (4-bromo-3-fluorophenyl)acetonitrile from Step 5 (6.4 g) in a solution of 7.5 mL of sodium hydroxide (50% in water WAV) were added l-bromo-2-chloroethane (4.0 mL) and benzyltriethylammonium chloride (204 mg). The mixture was heated at 600C for 5 hours. The reaction mixture was cooled to room temperature and poured into water (100 mL). The aqueous phase was extracted with ethyl acetate (200 mL). The combined organic extracts were washed with water (100 mL), hydrogen chloride (100 mL, 10% HCl in water) and brine and then dried with magnesium sulfate and the solvent removed in vacuo. The residue was purified by swish using methyl t- butyl ether and hexanes to yield the title compound.1H NMR (CD3COCD3) delta 7.69-7.73 (1 H, m), 7.28 (1 H, d), 7.25 (1 H, d), 1.80-1.87 (2 H, m), 1.59-1.65 (2H, m).

According to the analysis of related databases, 499983-13-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK FROSST CANADA LTD.; WO2006/133559; (2006); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts