Category: nitriles-buliding-blocks

6330-25-2, name is 2-Cyano-N-methyl-acetamide, 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. Application In Synthesis of 2-Cyano-N-methyl-acetamide

General procedure: 4-Amino-7-X-8-bromo-N-(alkyl)-cinnoline-3-carboxamide (X = H or F).To a solution of 2-[(3-X-2-bromophenyl)-hydrazono]-N-(alkyl)-2-cyanoacetamide (1.0 equiv) in anhydrous toluene (0.1 M, 1 volume) was added aluminum chloride (3.0 equiv). The reaction was heated with vigorous stirring at 70-90 C for 1-3 h, cooled, and quenched with Rochelle’s salt (saturated aqueous potassium sodium tartrate, 0.5 volume). Afterward, the mixture was stirred at room temperature overnight. The aqueous layer was separated, and the organic layer was treated with fresh Rochelle’ salt (0.5 volume) while stirring at room temperature for 1 h. After separating the resulting layers, the organic suspension was washed with water and filtered to give give a tan solid. Additionally, the organic filtrate was concentrated, and triturated with ether to give a tan precipitate. The resulting solids were filtered to give a tan solid in 30-70% yield of crude product. The combined tan solid was dried at 50 C under high-vacuum to give the title compound, which was used without further purification.The intermediate compounds were prepared as follows:2-[(3-X-2-Bromophenyl)-hydrazono]-N-(alkyl)-2-cyanoacetamide (X = H or F).Solution A: To a mechanically stirred solution of 3-X-2-bromoaniline (1.0 equiv) in acetic acid (2 M, 1 volume) was added water (0.6 volume) at ambient temperature. The mixture was cooled to 0 C, and then concentrated aqueous HCl (0.5 volume) added. A precipitate was formed immediately and the suspension was stirred at 0 C for 20 min. To this suspension was added dropwise a solution of sodium nitrite (1.10 equiv) in water (0.6 volume), maintaining the internal temperature below 5 C. The resulting clear orange solution was stirred at 0 C for another 30 min.Solution B: To a mechanically stirred solution of N-(alkyl)-2-cyanoacetamide (1.25 equiv) in ethanol (4.5 volume) was added a solution of sodium acetate (1.60 equiv) in water (120 volume), and chilled to between 0 C and -5 C.Solution A was poured into solution B, maintaining the internal temperature below 0 C. An orange precipitate was formed gradually. The mixture was stirred below 0 C overnight, and then the orange precipitate was collected by filtration, washed with water (100 mL ¡Á 3), and dried at 50 C under high vacuum to remove water. An orange solid was obtained in greater than 95% yield, which was the ‘E’, and used for the next step without further purification.

The synthetic route of 6330-25-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Alhambra, Cristobal; Becker, Chris; Blake, Timothy; Chang, Amy; Damewood Jr., James R.; Daniels, Thalia; Dembofsky, Bruce T.; Gurley, David A.; Hall, James E.; Herzog, Keith J.; Horchler, Carey L.; Ohnmacht, Cyrus J.; Schmiesing, Richard Jon; Dudley, Adam; Ribadeneira, Maria D.; Knappenberger, Katherine S.; MacIag, Carla; Stein, Mark M.; Chopra, Maninder; Liu, Xiaodong F.; Christian, Edward P.; Arriza, Jeffrey L.; Chapdelaine, Marc J.; Bioorganic and Medicinal Chemistry; vol. 19; 9; (2011); p. 2927 – 2938;,
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Synthetic Route of 7153-22-2,Some common heterocyclic compound, 7153-22-2, name is Ethyl 4-cyanobenzoate, molecular formula is C10H9NO2, 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.

General procedure: To a solution of hydroxylammonium chloride (1 eq.) in absolute ethanol (0.75 M) triethylamine (1 eq.) and starting compound (21 or 22) were added. The resulting solution was stirred at 60 C for 15 h. The solvent was removed under reduced pressure and residue dissolved in EtOAc, which was further washed with saturated solution of NaHCO3 and brine. The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure to give product 23 or 24.

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

Reference:
Article; Trstenjak, Uro?; Ila?, Janez; Kikelj, Danijel; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 302 – 313;,
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Electric Literature of 1080-74-6, 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. 1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a degassed solution of compound 10-5 (150 mg, 0.1 1 mmol) and pyridine (0.6 cm3) in anhydrous chloroform (40 cm3) at 0 C was added a degassed solution of 2-(3-oxo-indan-1 -ylidene)-malononitrile (86 mg, 0.440 mmol) in anhydrous chlorofornn (8 cm3). The resulting solution was then degassed for a further 30 minutes. The ice bath was removed and the reaction mixture warmed to 23 C and stirred for 18 hours. The reaction mixture was diluted with acetonitrile (150 cm3) and stirred for 1 hour. The solid collected by filtration and washed with acetonitrile (100 cm3) and methanol (100 cm3). The crude was then purified by column chromatography (dichloromethane) followed by trituration in acetonitrile (100 cm3) to give compound 1 1 (183 mg, 97%) as a dark green solid. 1H- NMR (400 MHz, CD2CI2) 0.67 – 0.80 (24H, m), 1.1 1 – 1.23 (48H, m), 1.36 – 1.55 (16H, m), 2.43 (16H, t, J 7.7), 6.78 – 6.92 (12H, m), 7.63 – 7.74 (4H, m), 7.78 – 7.87 (4H, m), 8.60 (2H, d, J 7.3), 8.80 (2H, s).

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-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; HEARD, Kane; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (260 pag.)WO2019/52935; (2019); A1;,
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Electric Literature of 63069-50-1, 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. 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

(3) In the same manner as that described in Example 3(4), a reaction was carried out using 4-amino-3-fluorobenzonitrile (129 mg, 0.95 mmol), obtained in Example 25(2), trimethylaluminium (0.89 ml, 1.07M n-hexane solution, 0.95 mmol) and methyl 4-[(trans-5-[[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]thio]-1,3-dioxan-2-yl]benzoate (120 mg, 0.24 mmol), obtained in Example 12 (1), and the reaction mixture was treated using a similar procedure to that described in Example 3(4) to afford the title compound (134 mg, yield 92%) as a white solid which was recrystallized from ethyl acetate-hexane to give white powdery crystals. Melting point: 136 C. NMR spectrum (500 MHz, CDCl3) delta ppm: 1.22 (3H, d, J=7 Hz), 3.36 (1H, q, J=7 Hz), 3.4-3.6 (1H, m), 3.76 (1H, t, J=11 Hz), 3.79 (1H, t, J=11 Hz), 4.42 (1H, ddd, J=11, 5, 2 Hz), 4.55 (1H, ddd, J=11, 5, 2 Hz), 4.85 (1H, d, J=14 Hz), 5.05 (1H, d, J=14 Hz), 5.05 (1H, s), 5.55 (1H, s), 6.7-6.8 (2H, m), 7.3-7.4 (1H, m), 7.45 (1H, d, J=12 Hz), 7.53 (1H, d, J=8 Hz), 7.66 (2H, d, J=8 Hz), 7.79 (2H, s), 7.91 (2H, d, J=8 Hz), 8.22 (1H, bd, J=4 Hz), 8.73 (1H, t, J=8 Hz). IR spectrum: nu max (KBr) cm-1: 3435, 2232, 1686, 1520, 1139. Mass spectrum m/z (FAB): 610 (M++1).

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

Reference:
Patent; SANKYO COMPANY, LIMITED; US2003/176480; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 939-83-3, name is 2-Methyl-5-nitrobenzonitrile, 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 939-83-3, Computed Properties of C8H6N2O2

A mixture of 2-cyano-4-nitrotoluene (10 g, 6.17 mmol), benzaldehyde (6.51 g, 6.17 mmol) and potassium carbonate (20 g) in MeOH (200 mL) was heated at reflux for 10 min. The mixture was cooled to ambient temperature over 30 min, whereupon precipitation of the product was complete. The product was isolated by filtration and washed successively with 1N HCl, water and MeOH then air dried. There was obtained 13.0 g of the benzamide (mp 269.8 C.) as evident from the lack of a nitrile adsorption in the IR and the appearance of peaks at 3357.1, 3193.6 (-NH2) and 1648.7 cm-1 (H2NC(O)-); LRMS (M-NO)+ m/z=238.

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-Methyl-5-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DuPont Pharmaceuticals Company; US6339099; (2002); B1;,
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Some common heterocyclic compound, 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, molecular formula is C11H19NO4, 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. name: Ethyl 2-cyano-4,4-diethoxybutyrate

Compound 44 (2.5 g, 10.7 mmol) and 2-cyano-4,4-diethoxy-butyric acid ethyl ester (3.2 g, 13.0 mol) were suspended in 15 mL of sodium ethoxide solution (2.8 g of sodium dissolved in 60 mL of ethanol), and the reaction mixture irradiated with microwave at 140 0C for 30 min. TLC (DCM: MeOH = 10:1) showed the starting material was reacted completely. The reaction mixture was cooled and evaporated under reduced pressure to get the residue, which was dissolved in a mixture of water (20 mL) and EtOAc (20 mL). The aqueous layer was extracted with EtOAc (20 mL x 3). The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated to afford the title compound (4.0 g, 90percent) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 52133-67-2, its application will become more common.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
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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

General procedure: 1H-Pyrazol-5-amine 1 (1 equiv.), 3-oxopropanenitrile 2 (1 equiv.), benzaldehyde 3 (1 equiv.), and Et3N (2 equiv.) were stirred in DMF (1 M) at 90 C for 16 h. The volatiles were removed under reduced pressure (or positive N2 (g) pressure). Sodium nitrite (3 equiv.) and acetic acid (134 equiv.) were added to the crude material, and the reaction mixture was stirred for 10 min. The volatiles were removed under reduced pressure (or positive N2 (g) pressure), and the crude reaction mixture was subjected to silica gel column chromatography with ethyl acetate in hexanes.

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:
Article; Hill, Matthew D.; Synthesis; vol. 48; 14; (2016); p. 2201 – 2204;,
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Adding a certain compound to certain chemical reactions, such as: 33279-01-5, name is 3-Oxopentanenitrile, 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 33279-01-5, Recommanded Product: 3-Oxopentanenitrile

A solution of 3-OXO-PENTANENITRILE (0. 5 g, 5.15 mmol) and methylhydrazine (0.24 g, 5. 15 mmol) in ethanol (5ML) is heated to reflux for 1.5 hours. The solvent is evaporated and the residue partitioned between ethyl acetate and brine. The organic phase is dried over MGS04 and evaporated to afford 5-ETHYL-2-METHYL-2H-PYRAZOL-3-YLAMINE. [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; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/26113; (2005); A1;,
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Reference of 107-91-5, 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 107-91-5 as follows.

Add 13.8 g (0.1 mol) to a 250 mL three-necked bottlePotassium carbonate, dissolved in 100 mL of water, added 11.0 g (0.1 mol)Acetylacetone, 8.4 g (0.1 mol) of cyanoacetamide was added in portions at room temperature.During the feeding process, the temperature slowly rises by about 10 C.A large amount of solid precipitated out as the reaction proceeded. After 24 h, the reaction was stopped by TLC (MeOH: DCM = 1: 20) and filtered.The filter cake was washed three times with water.Dry to give 14 g of a white solid.The solid was recrystallized from 1 L of methanol.13.0 g of a white needle-like solid was obtained in a yield of 87.8%.

According to the analysis of related databases, 107-91-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shenyang Pharmaceutical University; Chen Guoliang; Wang Lihui; Zhou Qifan; Du Fangyu; Dong Xiaoyu; Yang Jingyu; Wu Chunfu; (48 pag.)CN109320499; (2019); A;,
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Related Products of 2338-76-3, 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. 2338-76-3, name is 3-(Trifluoromethyl)phenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-(3-(trifluoromethyl)phenyl)acetonitrile (3.000 g, 16.203 mmol) and sodium hydride (60.00percent, 1.426 g, 35.647 mmol) in N,N-dimethylformamide (100 mL) at 0 ¡ãC, After the addition of 1,3-dibromopropane (1.731 mL, 16.203 mmol) this mixture was stirred at room temperature for 17 hours, a saturated aqueous solution of sodium bicarbonate (10 mL) was added to the reaction mixture at room temperature and the reaction was stirred for 10 minutes. The solvent was removed from the reaction mixture under reduced pressure, the obtained concentrate was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The concentrate was purified by column chromatography (SiO2, 40 g cartridge; ethyl acetate / hexane = 0percent to 5percent) and concentrated to give the title compound (0.945 g, 25.9percent) as a colorless oil.

The synthetic route of 3-(Trifluoromethyl)phenylacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chong Kun Dang Co., Ltd.; Kim, Yoon Tae; Lee, Chang Sik; Oh, Jung Taek; Song, Hey Sung; Choe, Jin; Lee, Jae Young; (210 pag.)KR2017/43091; (2017); A;,
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