Category: nitriles-buliding-blocks

Synthetic Route of 621-50-1, A common heterocyclic compound, 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, molecular formula is C8H6N2O2, 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.

(c) 5-Phenyl-furan-2-carboxylic acid [3-(lH-tetrazol-5- ylmethyl)-phenyl]-amide (75); (i) (3-Amino-phenyl)-acetonitrile (80); A solution of 3-nitrophenyl acetonitrile (500 mg, 3.1 mmol) in 5% AcOH (10 ml) was heated to 80C. Iron powder (1.5 g, 27 mmol) was then added and the resulting mixture stirred for 2 h. The reaction mixture was filtered through celite and the filter cake washed with MeCN (4 x 50 ml). The combined MeCN layers were evaporated in vacuo and the residue was re-dissolved in EtOAc (30 ml) followed by 2M HC1 (30 ml). The aqueous layer was separated, basified to pH 10 with 6M NaOH, and extracted with EtOAc (3 x 80 ml). The combined organic layers were dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound. Yield: 140 mg, 34% ; 1H NMR (400 MHz, CDC13) : 5 3.65 (s, 2H), 3.75 (s, 2H), 6.60-6. 70 (m, 3H), 7.15 (t, 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; PHARMAGENE LABORATORIES LIMITED; WO2005/80367; (2005); A1;,
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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 64248-64-2 as follows. Product Details of 64248-64-2

EXAMPLE 37 N-(2-Cyano-4-fluorophenyl)-4-piperidone propylene ketal (39) A mixture of 2,5-difluorobenzonitrile (2.272 g, 16.33 mmol) and 4-piperidone propylene ketal (2.570 g, 16.34 mmol) was stirred at room temperature (11 d). The resulting mixture was diluted with dichloromethane and sodium carbonate solution and the aqueous layer was extracted with two additional portions of dichloromethane. The combined organic extracts were washed with brine and dried over Na2SO4. The solvent was removed in vacuo. PCTLC (SiO2, 6 mm, 20% EtOAc-80% hexane) afforded the title compound (39). 1H NMR (CDCl3, 400 MHz) consistent with assigned structure. FABLRMS m/e 277 g/mole (M++H, C15H17FN2O2=277 g/mole.) HPLC (Vydac; C18; diameter=4.6 mm; length=150 mm; gradient=H2O [0.1% H3PO4]-CH3CN, 95%-5%, 5%-95%, over 16 minutes, 2 ml/min flow rate) RT=7.31 min; focus=215 nm; 99.3% pure.

According to the analysis of related databases, 64248-64-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck & Co., Inc; Synaptic Pharmaceutical Corporation; US6376503; (2002); B1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, 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 4640-67-9, Computed Properties of C9H6FNO

To a solution of 3-(4-fluorophenyl)-3-oxopropanenitrile (1 g, 6.13 mmol) in ethanol (11 mL) was added hydrazine hydrate (1.82 mL, 36.8 mmol). The reaction mixture was stirred at 100C in a sealed vessel for 6 h. The solvents were evaporated in vacuo and the residue was extracted with EtOAc and brine. The organic solvents were dried over magnesium sulphate and evaporated in vacuo. The residue (1.18 g) was dissolved in EtOAc (anhydrous), then the procedure for Intermediate 1 was applied. The title compound (914 mg, 57%) was isolated as a white powder. C NMR delta (DMSO-d6, 75 MHz) 173.19, 163.01 (d, JCF 245.0 Hz), 154.61, 141.81, 141.59, 128.63 (2C, d, JCF 8.4 Hz), 127.97, 115.94 (2C, d, JCF 21.6 Hz), 86.88. MS (m/z) 263 [M+H]+.

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, 3-(4-Fluorophenyl)-3-oxopropanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; HORSLEY Helen Tracey; HUANG Qiuya; NEUSS Judi Charlotte; REUBERSON James Thomas; VANDERHOYDONCK Bart; WO2015/193169; A1; (2015);,
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Related Products of 67832-11-5, 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. 67832-11-5 name is 4-Bromo-2-methylbenzonitrile, 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.

To a solution of 4-bromo-2-methylbenzonitrile (3 g, 15 mmol) in THF (20 mL) was added BH3¡¤THF (45 mL, 45 mmol) at 0 C. The solution was stirred for 1 h and heated to 80 C for 2 h. The mixture was quenched with H2O and extracted with EtOAc (50 mL x 3). The organic layer was concentrated in vacuo to afford a residue which was suspended in saturated HCl/EtOAc and filtered. The filter cake was washed with diethyl ether (20 mL x 3) and dried under vacuum to afford the desired product (2.1 g, yield 69%) as white solid. ESI-MS (M+H)+: 200.1.

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

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian T.; MA, Bin; CHAN, Timothy Raymond; KUMARAVEL, Gnanasambandam; MIAO, Hua; BERTOLOTTI-CIARLET, Andrea; OTIPOBY, Kevin; WO2015/89327; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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 654-70-6, name: 4-Cyano-3-trifluoromethylaniline

At room temperature, 1 ml of thiophosgene is added to 22 ml of water to form a suspension.Then 2.23 g of 4-amino-2-trifluoromethylbenzonitrile was added dropwise to the above solution.The dropwise addition time was 20 minutes, and after completion of the dropwise addition, stirring was continued for 1 hour at room temperature. After completion of the reaction, the reaction solution was extracted with 2 x 20 ml of methylene chloride. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure (about 0.4 mmHg) to give 2.72 g of the title compound,Brown 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-Cyano-3-trifluoromethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Beijing Haimeiyuan Pharmaceutical Technology Co., Ltd.; Wang Yingzhao; Di Wei; Liu Yanling; (34 pag.)CN104341351; (2018); B;,
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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. 6609-57-0, name is 2-Ethoxybenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C9H9NO

2-ethoxy benzonitrile (25g, 170 mmol) was added to an ice cold solution of chloro sulfonic acid (183.7g, 1.57mol) over a period of one hour. The temperature of the reaction mixture was maintained at about 5C to 7C. The reaction mixture was stirred at about 5C to 7C overnight. The reaction mass was added into ice water (500 mL) slowly at 100C to 15C. The suspension was stirred for about 1 hour, filtered under nitrogen atmosphere to obtain 5-chlorosulfonyl-2-ethoxy benzonitrile as yellow solid which was used directly in next step.

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; RANBAXY LABORATORIES LIMITED; MITTAL, Anu; KHANNA, Mahavir, Singh; THAPER, Rajesh, Kumar; PRASAD, Mohan; WO2011/16016; (2011); A1;,
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Synthetic Route of 63069-50-1, The chemical industry reduces the impact on the environment during synthesis 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, I believe this compound will play a more active role in future production and life.

EXAMPLES 11-28Synthesis of Examples 11-28 were prepared following General Procedures l-lll. General Procedure I. Preparation of Dimethylamino Compounds 2a-iTo mixture of 1a-i (1 mmol) and NaH (2.6 mmol) in anhydrous THF (4 ml.) was added CH3I (2.6 mmol). The reaction mixture was stirred at room temperature for 3-12 hours, monitoring by TLC. The reaction was quenched by adding small amount of CH3OH, then H2O, the mixture was then concentrated and extracted three times with EtOAc. The combined extracts were washed with H2O, then dried over Na2SO4. Separation and purification (hexane/EtOAc = 10:1 or 10:2) gave the following compounds. 4-Dimethylamino-3-fluoro-benzonitrile, MS: m/z 165 (M + H)

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-Amino-3-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WYETH; WO2009/120826; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A common compound: 4110-35-4, name is 3,5-Dinitrobenzonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 4110-35-4

Example 137Alternative Preparation of 3-(4,5-dihydro-4-methyl-5-oxotetrazol-1-yl)-5-nitrobenzonitrileA mixture of 3,5-dinitrobenzonitrile (386 mg, 2.0 mmol), 1-methyl-1H-tetrazol-5(4H)-one (400 mg, 4.0 mmol) and K2CO3 (552 mg, 4.0 mmol) in NMP (6 mL) was heated to 110 C. and stirred overnight. After allowing to cool, the mixture was poured in to H2O (75 mL) and EtOAc (40 mL). The aqueous and organic layers were partitioned and the aqueous layer was extracted with EtOAc (2¡Á30 mL). The combined organic extracts were washed with brine (1¡Á20 mL), dried (Na2SO4), filtered and the solvent removed under vacuum to leave a crude residue. The residue was purified by column chromatography on silica gel using EtOAc/hexane (3:7 to 4:6) as eluent to give the product (182 mg, 37%) as a solid.Data identical to previously synthesized material. (Example 136)Note: 1-methyl-1H-tetrazol-5(4H)-one was prepared according to procedure detailed in EP643049 (1995); Preparation of 1-substituted-5(4H)-tetrazolinones by desulfurization of tetrazolinethiones, which is hereby incorporated by reference.

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, 4110-35-4, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Singh, Rajinder; Tso, Kin; Zhang, Jing; Duncton, Matthew; Alvarez, Salvador; Kolluri, Rao; Ramphal, John; Holland, Sacha; US2011/130415; (2011); A1;,
Nitrile – Wikipedia,
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215800-25-2, These common heterocyclic compound, 215800-25-2, name is 2-(4-Bromo-3-methylphenyl)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.

Step d intermediate 472-(4-bromo-3-methylphenyl)-2-methylpropanenitrileTo a stirred solution of 2-(4-bromo-3-methylphenyl)acetonitrile (11.2 g, 53.3 mmol) in anhydrous DMF (125 mL) is added methyl iodide (13.2 mL, 213 mmol). The solution is cooled to O0C and sodium hydride (60% susp. in oil, 3.84 g, 160 mmol) is added in small portions over 20 min. The reaction mixture is then left stirring and slowly warmed up to room temperature for 18 h. At O0C, water (500 mL) is then slowly added then extracted with ethyl acetate containing 10% of hexanes. The organic layer is separated, dried with MgSO4, filtered and concentrated under reduced pressure to provide the expected product 2-(4-bromo-3-methylphenyl)-2- methylpropanenitrile (12.6 g, 99 %) as a clear yellow oil which is used in the next step without further purification. IH NMR (400 MHz, CHLOROFORM-D) 5 ppm 1.71 (s, 6 H) 2.43 (s, 3 H) 7.14 (dd, /=8.40, 2.34 Hz, 1 H) 7.34 (d, /=2.54 Hz, 1 H) 7.53 (d, /=8.40 Hz, 1 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 215800-25-2.

Reference:
Patent; ASTRAZENECA AB; WO2008/18827; (2008); A1;,
Nitrile – Wikipedia,
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4426-11-3, A common heterocyclic compound, 4426-11-3, name is Cyclobutanecarbonitrile, molecular formula is C5H7N, 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.

Example 163A 1-cyclopentylcyclobutanecarbonitrile To a solution of cyclobutanecarbonitrile (405 mg, 5 mmol) in THF (7 mL) was added dropwise LDA (2.0 M, 2.5 mL, 5 mmol) at -78 C. over 10 minutes. After stirring for 30 minutes, a solution ofbromocyclopentane (888 mg, 6.0 mmol) in HMPA (268 mg, 1.5 mmol) was added and the mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched with the addition of 1N aqueous HCl (10 mL) and extracted with EtOAc (20 mL*3). The combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography (petroleum ether/EtOAc=20/1) to give Example 163A (0.46 g, yield 62.3%) as a colorless oil. 1H NMR (400 MHz, CDCl3): delta 2.53-2.44 (m, 2H), 2.25-2.07 (m, 4H), 2.03-1.95 (m, 1H), 1.86-1.69 (m, 4H), 1.62-1.54 (m, 2H).

The synthetic route of Cyclobutanecarbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Inc.; Bayburt, Erol K.; Clapham, Bruce; Cox, Phil B.; Daanen, Jerome F.; Dart, Michael J.; Gfesser, Gregory A.; Gomtsyan, Arthur; Kort, Michael E.; Kym, Philip R.; Schmidt, Robert G.; Voight, Eric A.; US2013/131036; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts