Month: December 2020

Application of 13338-63-1,Some common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, molecular formula is C11H13NO3, 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 1 Preparation of (Z)-3-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile 3.0 g of 3-nitro-4-methoxybenzaldehyde, 3.4 g of 3,4,5-trimethoxyphenylacetonitrile, 800 mg of sodium hydroxide and 100 mg of octylmethylammonium chloride were dissolved in 15 ml of water and 15 ml of dichloromethane and reacted for 4 hours at room temperature. Ice water was added to the reaction liquid, which was then extracted three times each with dichloromethane. The extract was dried with anhydrous sodium sulfate and concentrated. The concentrated liquid was purified by crystallization (ethyl acetate) to obtain 4.4 g of the intended compound. The yield was 72%. 1 H-NMR(CDCl3): 8.30 (1H, dd, J=2.4, J=9.0), 8.21 (1H, d, J=2.4), 7.38 (1H, s), 7.21 (1H, d, J=9.0), 6.86 (2H, s), 4.05 (3H, s), 3.94 (6H, s), 3.89 (3H, s); mass spectrum (m/z): 370 (M+); melting point 191-192 C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4,5-Trimethoxyphenylacetonitrile, its application will become more common.

Reference:
Patent; Ajinomoto Co., Ltd.; US5525632; (1996); 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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, A new synthetic method of this compound is introduced below., Computed Properties of C8H5F3N2

A mixture of 9.46 g of 3-(5-chloropentyl)-4-methyl-2,5-furandione and 8.13 g of 4-amino-2-(trifluoromethyl)benzonitrile in 22 ml of ethanol was mixed under a nitrogen atmosphere with 2.5 g of an activated molecular sieve (0.3 nm), and it was stirred for 2 days at 90 C. For working-up, the molecular sieve was filtered off after cooling, washed with ethanol, and the combined ethanol solutions were concentrated by evaporation. The residue was taken up in ethyl acetate and washed with water as well as saturated sodium chloride solution. After drying on sodium sulfate and concentration by evaporation, it was chromatographed on silica gel with ethyl acetate/hexane/toluene, and 11.69 g of the title compound was thus obtained as a white solid. 1H-NMR (300 MHz, CDCl3): delta [ppm]=8.06 sbr (1H, aryl); 7.91 s (2H, aryl); 3.56 t (J=7 Hz, 2H, CH2Cl); 2.53 t (J=7.5 Hz, 2H, CH2olefin); 2.11 s (3H, CH3); 1.83 m (2H, CH2); 1.69-1.50 m (4H, CH2).

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; Schering AG; US2004/9969; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 33279-01-5, A common heterocyclic compound, 33279-01-5, name is 3-Oxopentanenitrile, molecular formula is C5H7NO, 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.

A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.28 ml) and ethanol (45 ml) was heated at 70 C. for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material in 51% yield; 1H NMR: (DMSOd6) 1.04 (t, 3H), 2.41 (q, 2H), 4.4 (br s, 2H).

The synthetic route of 33279-01-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jung, Frederic Henri; Morgentin, Remy Robert; Ple, Patrick; US2009/76075; (2009); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 159847-81-1, name is Methyl 2-amino-5-cyanobenzoate, 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 159847-81-1, Product Details of 159847-81-1

b. 5-Cyano-2-[2-(3-methyl-isoxazol-5-yl)-acetylamino]-benzoic acid methyl ester A solution of 2-amino-5-cyano-benzoic acid methyl ester (1. 50G, 8.51 mmol) and (3-methyl-isoxazol-5-yl) -acetic acid (1.32 g, 9.36 mmol) in 40 ml of POCl3 was heated at 80 C for 2 hr and then cooled to RT. Treated with 50 mL of EtOAc, the mixture was washed with H20 (3 x 40 ml), sat. NAHC03 (40 ml), brine (40 ml) and dried (NA2S04). Removal of the solvent under reduced pressure gave 2.31 g (91 %) of product as a light yellow solid : H-NMR (CDC13 ; 400 MHz) 8 11.49 (s, 1H), 8.85 (d, 1H, J = 8.8 Hz), 8.35 (d, 1H, J = 2. 0 Hz), 7.79 (dd, 1H, J = 8. 8,2. 0 Hz), 6.20 (s, 1H), 3.97 (s, 3H), 3.95 (s, 2H), 2.33 (s, 3H). Mass spectrum (ESI, m/z) : Calcd. for CLSHL3N3O4 300.1 (M+H), found 299.9.

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; JANSSEN PHARMACEUTICA, N.V.; WO2005/9967; (2005); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 1953-99-7, These common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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.

100 mL flask Of Synthesis Example 1-2 4- (2-tert-Butyl-4-methoxy-phenoxy) -3,5,6-trichloro-phthalonitrile (1.1 g) 3,4,5,6-Tetrachlorophthalonitrile (0.71 g), 1,8-Diazabicycloundec-7-ene (1.02 g) And 1-pentanol (14 g) were added, and the mixture was heated at 90 ¡ã C to dissolve the solid. Then, zinc acetate (0.25 g) was added thereto and stirred while heating to 140 ¡ã C. After completion of the reaction, precipitation was confirmed with methanol, followed by filtration and vacuum drying. The dried solid is purified by column chromatography. Dichloromethane is appropriately added to the solid obtained after purification to dissolve the solid, and then methanol is added to crystallize. The crystallized solid is filtered and dried under vacuum to obtain a compound represented by the following general formula (10).

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Samsung SDI Co., Ltd; Shin Myeong-yeop; Seo Hye-won; Jeong Ui-su; Han Gyu-seok; (41 pag.)KR2019/27185; (2019); 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. 32703-80-3, name is 4-(tert-Butyl)phthalonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-(tert-Butyl)phthalonitrile

4-(4-Methoxycarbonylphenyl)phthalonitrile (0.15 g, 0.5 mmol) and /-butyl phthalonitrile (0.26g, 1.4 mmol) were placed in a reaction vessel under inert conditions. Pentanol (20 ml_) and DBU (0.1mL) were added thereto and the contents of the reaction vessel heated to approximately 136 C for approximately 24 hours. The solvent was removed under reduced pressure and to yield a solid, which was placed on to alumina and eluted with ethyl acetate; petroleum spirit (70 : 40) to yield a dark green residue.

According to the analysis of related databases, 32703-80-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CORUS UK LIMITED; HOLLIMAN, Peter; RUGEN-HANKEY, Sarah; WO2010/136178; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 6575-11-7,Some common heterocyclic compound, 6575-11-7, name is 2-Amino-6-chlorobenzonitrile, molecular formula is C7H5ClN2, 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.

A mixture of 2-amino-6-chlorobenzonitrile (17.72 g, 0.116 mol) and tetrahydro-2,5-dimethoxyfuran (0.116 mol) in HOAc (100 ml) was stirred and refluxed for 30 mm. Subsequently, the mixture was cooled and evaporated. The residue was purified over silica gel on a glass filter (eluent:DCM). The product fractions were collected and the solvent was evaporated. The residue was crystallized from EtOH. Yield: 18.83 g of intermediate 3 (80% yield).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-6-chlorobenzonitrile, its application will become more common.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; Meerpoel, Lieven; Maes, Louis Jules Roger Marie; de Wit, Kelly; Augustyns, Koen Jan Ludovicus; US2014/45827; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 5216-17-1,Some common heterocyclic compound, 5216-17-1, name is 2,3,5,6-Tetrafluorobenzonitrile, molecular formula is C7HF4N, 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: CZ-CZO (3.90 g, 4.08 mmol) and sodium hydride (0.6 g, 24.3 mmol) were added to dry tetrahydrofuran (THF, 20 mL), and the mixture was stirred at room temperature for 0.5 h.Further, 2,3,5,6-tetrafluorobenzonitrile (0.089 g, 0.51 mmol) was added, and the reaction was stirred at room temperature for 12 h. After completion of the reaction, the mixture was quenched with water and extracted with dichloromethane. Purification by column chromatography gave the final product C5, yield 75%

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3,5,6-Tetrafluorobenzonitrile, its application will become more common.

Reference:
Patent; Southeast University; Jiang Wei; Huang Suli; Sun Yueming; (21 pag.)CN108586318; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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, Recommanded Product: 4-Cyano-3-trifluoromethylaniline

To the reaction kettle, was introduced nitrogen gas, to which were added 4-cyano-3-(trifluoromethyl)phenylamine (200 g), n-heptane (450 mL), and water (500 mL), followed by stirring to produce suspension. Thiophosgene (148 g) was drop added. The mixture was stirred at 40 C. for 16 hours, then stood for liquid separation. The water phase was extracted with n-heptane (500 mL) once, and the organic phase was combined. The solvent was removed by concentrating under reduced pressure, followed by reduced pressure distillation to provide the target compound (220 g), with a yield of 89.8%. 1HNMR (DMSO, 400 MHz): 7.52 (1H, dd, J=1.7, 8.3), 7.60 (1H, d, J=1.7 Hz), 7.87 (1H, d, J=8.3 Hz).

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; HINOVA PHARMACEUTICALS INC.; CHEN, Yuanwei; DU, Wu; KUANG, Tongtao; GENG, Xi; (10 pag.)US2020/87261; (2020); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 40497-11-8, A common heterocyclic compound, 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, molecular formula is C7H8N2O2, 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.

250 mL round bottom three-necked flask0.01 mol of 4-methylaniline and a small amount of ethanol,3.0 mL (0.035 mol) of concentrated hydrochloric acid was added dropwise under ice-cooling with stirring.0.018 mol of sodium nitrite was dissolved in 10 mL of water,Slowly dropping into the flask,After the reaction was completed 0.5h yellow diazonium salt solution.0.01 mol of ethyl 2,3-dicyanopropionate was added to a three-necked flask,The prepared diazonium salt solution was dropped into the flask,After dropping the reaction 2 h. Adding ammonia,Adjust the pH to 9-10,Reaction at room temperature for 2h.After completion of the reaction, the reaction mixture was extracted with 40 mL of dichloromethane,The organic layer was washed with water (2 x 30 mL)Washed with saturated sodium chloride solution (1 x 40 mL)Dried over anhydrous magnesium sulfate,A portion of the solvent was evaporated under reduced pressure to crystallize to yield 1.20 g of product,Yield 60.5%

The synthetic route of 40497-11-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing University of Technology; Wan, Rong; Wu, Shaohua; Guo, Chunwei; Wang, Xinlin; Chen, Fuli; Han, Zhenyu; Fu, Xiaohuan; (13 pag.)CN105820167; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts