Category: nitriles-buliding-blocks

Reference of 29509-06-6, A common heterocyclic compound, 29509-06-6, name is 4-Methyl-3-oxopentanenitrile, molecular formula is C6H9NO, 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.

Hydroxylamine hydrochloride (10.3 g, 148 mmol) was slowly added to an ice cold solution of NaOH (25.9 g, 645 mmol) in water (73 mL) and the resulting solution was poured into a solution of crude 3-oxo-4-methylpentanenitrile while stirring. The resulting yellow solution was heated at 50 C for 2.5 hours to produce a less dense yellow oil. The warm reaction mixture was immediately extracted with CHCl3 (3 x 100 mL) without cooling. The combined organic layers were dried (MgSO4), and concentrated in vacuo. The resulting oily yellow solid was filtered through a pad of silica (10% acetone/90% CH2Cl2) to afford the desired isoxazole as a yellow solid (11.3 g, 70%): mp 63-65 C; TLC Rf (5% acetone/95% CH2Cl2) 0.19; 1H-NMR (DMSO-d6) d 1.12 (d, J=7.0 Hz, 6H), 2.72 (sept,J=7.0 Hz, 1H), 4.80 (s, 2H), 6.44 (s, 1H); FAB-MS m/z (rel abundance) 127 ((M+H)+; 67%).

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; Bayer Pharmaceuticals Corp.; EP1047418; (2005); B1;,
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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 2-Chloro-5-nitrobenzonitrile

3-Cyano-4-chloroaniline 2-Chloro-5-nitrobenzonitrile (25 g, 137 mmol) was dissolved in ethanol (275 mL). Stannous chloride dihydrate (154.5 g, 0.685 M) was added and the mixture stirred at 70 C. for 30 min. The mixture was then cooled to room temperature and poured into crushed ice. The mixture was made basic with solid sodium hydroxide. This mixture was extracted with ethyl acetate (3*100 mL). The extracts were combined, washed with brine, dried (MgSO4), concentrated and the residue dried under vacuum and recrystallized from ethanol to yield light brown needles (10.6 g, 51%).

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chapdelaine, Marc; Davenport, Timothy; Haeberlein, Markus; Horchler, Carey; McCauley, John; Pierson, Edward; Sohn, Daniel; US2004/110745; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 1187-42-4, name is Diaminomaleonitrile, 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 1187-42-4, Recommanded Product: 1187-42-4

General procedure: AlCl3 (15 molpercent) was added to a solution of DAMN (1 mmol), ketone (1 mmol) and isocyanide (1 mmol), in 5 ml of CH3CN. The resulting mixture was stirred for an appropriate time at room temperature. After completion of the reaction, as indicated by thin-layer chromatography (TLC; ethyl acetate=n-hexane 3=1), the product was precipitated by addition of 10 ml of water. The precipitate was filtered off, washed with water, and then recrystallized from acetone. In the case of aromatic aldehyde, precipitate after filtration was loaded on column chromatography with 20percent ethyl acetate?hexane as an eluent system to furnish the product.

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:
Article; Bhosale, Shrikar M.; Naik, Nilesh H.; Kusurkar, Radhika S.; Synthetic Communications; vol. 43; 23; (2013); p. 3163 – 3169;,
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. 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-Methyl-3-nitrobenzonitrile

General procedure: To a screw-capped vial (50 ml) were added iodobenzene 1a(1.0 mmol), substituted benzonitrile 2 (2.0 mmol), K2CO3 (276 mg,2.0 mmol), NaOH (40 mg,1.0 mmol), CuI (19 mg, 0.1 mmol), DMEDA(9 mg, 0.1 mmol), and [bmim]PF6 (14 mg, 0.05 mmol) in water(2 ml). The vial was flushed with nitrogen then sealed with the cap,and allowed to stir at 100 C for the specific reaction time. Thereaction mixture was extracted with EtOAc (315 ml). The combinedorganic extracts were dried over Na2SO4 for 12 h and evaporatedunder vacuum. The crude products were purified in a silicagel column for further purification, using PE/EtOAc (5:1) as theeluent.

According to the analysis of related databases, 939-79-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Jichao; Yin, Xinchi; Wu, Jun; Wu, Datong; Pan, Yuanjiang; Tetrahedron; vol. 69; 48; (2013); p. 10463 – 10469;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 6330-25-2, 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. 6330-25-2, name is 2-Cyano-N-methyl-acetamide, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Pyridine was added dropwise with stirring to cyanoacetamide 2a-e(15 mmol) in a round-bottom flask until complete dissolution of the cyanoacetamide. DMAP (18 mg, 0.15 mmol) and mercaptoacetic acid (3.2 ml, 46mmol) were added to the obtained solution. The obtained mixture was refluxed for 12 h in a flask equipped with a reflux condenser,then diluted with 0.5 HCl solution (5 ml).The precipitate of 1,3-thiazolidinone 1 was filtered off and washed with hot MeCN (15 ml). When necessary, the product was additionally purified by refluxing a suspension of thiazolidine in MeCN, followed by hot filtration.(2Z)-N-Methyl-2-(4-oxo-1,3-thiazolidin-2-ylidene)acetamide (1a). Yield 1.37 g (53%), white powder, mp 238-243(decomp.). IR spectrum, nu, cm-1: 1184, 1299, 1398,1415, 1470, 1556 (C=), 1624 (C=O), 1699 (C=O), 3312 (NH). 1H NMR spectrum, delta, ppm (J, Hz): 2.58 (3H, d, J= 4.8, CH3); 3.61 (2H, s, CH2); 5.55 (1H, s, CH); 7.61 (1H, br. s, NH); 11.20 (1H, s, NH). 13C NMR spectrum, delta, ppm: 25.3; 31.9; 92.4; 151.4; 167.0; 174.0. Mass spectrum, m/z(Irel, %): 172 []+(94), 142 [-NHCH3]+(100), 114 [-NHCH3-CO]+(55), 98 (30), 86 (37), 68 (78), 42 (35), 40 (22). Found, %: C 41.70; H 4.61; N 16.51. C6H8N2O2S. Calculated, %: C 41.85; H 4.68; N 16.27

The chemical industry reduces the impact on the environment during synthesis 2-Cyano-N-methyl-acetamide. I believe this compound will play a more active role in future production and life.

Reference:
Article; Obydennov, Konstantin L.; Galushchinskiy, Aleksei N.; Kosterina, Marya F.; Glukhareva, Tatiana V.; Morzherin, Yuri Yu.; Chemistry of Heterocyclic Compounds; vol. 53; 5; (2017); p. 622 – 625; Khim. Geterotsikl. Soedin.; vol. 53; 5; (2017); p. 622 – 625,4;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 57381-51-8,Some common heterocyclic compound, 57381-51-8, name is 4-Chloro-2-fluorobenzonitrile, molecular formula is C7H3ClFN, 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.

To commercially available 2-fluoro-4-chlorobenzonitrile 15a (2 g,12.8 mmol) dimethylamine (4equiv., 3.5 ml) was added and the solution was heated in closed vessel at 80C overnight. The reaction was evaporated and the residue was dissolved in AcOEt and washed with water and brine. The residue was purified by chromatographic column using EtOAc 1 / petroleum ether 9 as eluant obtaining 1.95 g of a transparent oil. Yield = 87% ‘HNMR (DMSO, 200 MHz) delta 3.01 (6H, s), 6.91 (1H, dd, J = 8.4 Hz, J’ = 2 Hz), 7.02 (1H, d, J = 2 Hz), 7.60 (1H, d, J = 8.4 Hz)

The synthetic route of 57381-51-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMESTE S.R.L.; NAPOLETANO, Mauro; TREVISANI, Marcello; PAVANI, Maria Giovanna; FRUTTAROLO, Francesca; WO2011/120604; (2011); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 6136-68-1 as follows. Quality Control of 3-Acetylbenzonitrile

Example 10 Synthesis of alpha-Bromo-3-cyanoacetophenone (Compound 10) A solution of bromine (0.92 mL, 17.9 mmol) in 8 mL dichloromethane was added to 3-cyanoacetophenone (2.60 g, 17.9 mmol) in 11 mL dichloromethane over 10 min at 5-10 C. The mixture was warmed to room temperature and stirred for 1 hour. Water (25 mL) was added to the mixture. The organic layer was separated, dried over Na2 SO4, and concentrated to a yellow solid (3-50 g). The yellow solid was recrystallized from 95% EtOH to afford compound 10 as white crystals. Yield: 2.22 g (55%). The properties of alpha-bromo-3-cyanoacetophenone are listed below: 1 H NMR (CDCl3, 300 MHz) delta 8.08 (m,2H), 7.81 (m, 2H), 4.43 (s, 2H). 13 C NMR (CDCl3, 75 MHz, APT) delta 189.58 (C), 136.77 (CH), 134.71 (C), 132.66 (CH), 130.02 (CH), 117.69 (C), 113.53 (C), 30.07 (CH2).

According to the analysis of related databases, 6136-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Scriptgen Pharmaceuticals, Inc.; US5668165; (1997); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 179897-89-3, 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. 179897-89-3 name is 5-Bromo-2-fluorobenzonitrile, 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.

At room temperature,to2-Fluoro-5-bromobenzonitrile (5.0 g)Soluble in ethanol (30mL)80% hydrated hydrazine (7.82g) was added to the solution.After refluxing at 90 C. for 12 h, the reaction solution was cooled to room temperature.Concentrate under reduced pressure to remove the ethanol.The residue was slurried with dichloromethane for 1 h.Filter, wash with dichloromethane, dry,The title compound (5.3 g) was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Beijing Sai Lintai Pharmaceutical Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; Zhu Li; Hu Yuandong; Dai Liguang; Yang Yanqing; Duan Xiaowei; Yang Zhao; Wu Wei; Sun Yinghui; Han Yongxin; Peng Yong; Luo Huiyan; Luo Hong; Yang Ling; Xu Hongjiang; Guo Meng; Zhong Zhaobo; Wang Shanchun; (102 pag.)CN108003161; (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. 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3759-28-2

Step B 4-Cyano-N-(1,1-dimethylethoxy)carbonyl-4-(2-cyanophenyl)piperidine A solution of bis(2-chloroethyl)-N-(1,1-dimethylethoxy)carbonyl amine (19 g, 78 mmol) and homophthalonitrile (8.6 g, 60 mmol) and cesium carbonate (79 g, 241 mmol) was stirred at 60 C. for 12 hours. The solution cooled to room temperature and diluted with 500 ml EtOAc and washed with saturated aqueous NaHSO4 and saturated aqueous NaCl. The solution was dried over Na2SO4, concentrated in vacuo, and purified by PCTLC (30% EtOAc in Hexane) to afforded 4-cyano-N-(1,1-dimethylethoxy)carbonyl-4-(2-cyanophenyl) piperidine as a yellow/orange oil. 1H NMR (CDCl3): delta7.81-7.79 (d, 2H), 7.67-7.65 (m, 2H), 7.51-7.47 (m, 1H), 4.31 (br s, 2H), 3.26 (br s, 2H), 2.33-2.20 (m, 4H), 1.48 (s, 9H).

The synthetic route of 3759-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6319932; (2001); B1;,
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. 935-02-4, name is 3-Phenylpropiolonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H5N

4.4.1 (Z+E)-3-(3-Methyl-2-selenoxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile (4a) To a mixture of acetylene 2 (64.0 mg, 0.5 mmol) and Se (40.0 mg, 0.5 mmol) in MeCN (1 mL) was added 1-methylimidazole (1a; 41.0 mg, 0.5 mmol) in MeCN (1 mL). The mixture was stirred at 82 C for 5 h. After cooling to 20-25 C, the solvent was removed and column chromatography afforded selone (Z)-4a (46 mg, 39%) as a yellow microcrystalline powder, mp 208-209 C (ethanol). Initial imidazole 1a was recovered (7 mg, conversion was 83%). Initial Se was recovered (20 mg, conversion was 50%). Z:E-isomers ratio was 5:1 [(E)-isomer, 5%, data 1H NMR]. (Z)-Isomer: 1H NMR (400.13 MHz, CDCl3): delta=7.50-7.27 [m, 5H, Ho,m,p from C(6)-Ph], 7.07 (s, 1H, 4-H), 6.98 (s, 1H, 5-H), 6.12 (s, 1H, 7-H), 3.76 (s, 3H, N-CH3) ppm. 13C NMR (100.62 MHz, CDCl3): delta=159.2 (C-2), 154.9 (C-6), 132.4 [Ci from C(6)-Ph], 132.0 [Cp from C(6)-Ph], 129.3 [Cm from C(6)-Ph], 127.0 [Co from C(6)-Ph], 121.7 (C-4), 119.3 (C-5), 114.5 (CN), 97.7 (C-7), 37.5 (N-CH3) ppm. (E)-Isomer: 1H NMR (400.13 MHz, CDCl3): delta=7.50-7.45 [m, 5H, Ho,m,p from C(6)-Ph], 6.94 (s, 1H, 7-H), 6.90 (s, 1H, 4-H), 6.65 (s, 1H, 5-H), 3.73 (s, 3H, N-CH3) ppm. IR (KBr): 2222 (CN), 1622 (C=C), 1368 (C=Se) cm-1. Anal. Calcd for C13H11N3Se (288.21): C, 54.18; H, 3.85; N, 14.58; Se, 27.40. Found: C, 54.50; H, 3.99; N, 14.52; Se, 27.07.

According to the analysis of related databases, 935-02-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Belyaeva, Kseniya V.; Andriyankova, Ludmila V.; Nikitina, Lina P.; Mal’Kina, Anastasiya G.; Afonin, Andrei V.; Ushakov, Igor A.; Bagryanskaya, Irina Yu.; Trofimov, Boris A.; Tetrahedron; vol. 70; 5; (2014); p. 1091 – 1098;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts