Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 1483-54-1, name is 2-Amino-4-(trifluoromethyl)benzonitrile, 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 1483-54-1, Product Details of 1483-54-1

Potassium iodide (5.6 g, 34 mmol) and sodium nitrite (2.4 g, 35 mmol) were added to a solution of 2-amino-4-trifluoromethyl-benzonithle (2.58 g, 14 mmol) in acetonithle (60 ml_). The resultant mixture was cooled to 0 C in an ice-water bath with magnetic stirring. Ice-cold concentrated HCI (14 ml_) was added slowly drop-wise to the reaction mixture, causing the reaction mixture to become cloudy and deep red in color. The reaction mixture was stirred at 0 C for 30 minutes, then warmed to room temperature. Stirring at room temperature proceeded for 3 hours. The reaction mixture was poured into water, and the resulting suspension was extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered, and concentrated to give a purple liquid. A solution of this crude product and dichloromethane (200 ml_) was evaporated onto silica gel, and the dry silica gel-supported product was loaded onto a silica gel column. Manual flash chromatography using 5% ethyl acetate in hexanes afforded 2-iodo-4-trifluoromethyl-benzonithle as 3.58 g (87%) of a purple, crystalline solid.

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-Amino-4-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FIROOZNIA, Fariborz; GILLESPIE, Paul; LIN, Tai-An; MERTZ, Eric; SIDDURI, Achyutharao; SO, Sung-Sau; TAN, Jenny; THAKKAR, Kshitij Chhabilbhai; WO2010/55005; (2010); 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 19179-31-8 as follows. category: nitriles-buliding-blocks

General procedure: 2-cyanopyridine (2.5g, 24.01mmol) was dissolved in EtOH (60mL) treated with K2CO3 (5.97g; 43.22mmol; 1.8 equiv) and H2NOH·HCl (3.0g; 43.22mmol; 1.8 equiv) and heated to reflux for 12h. The mixture was diluted with diethyl ether when it was cooled to room temperature. The product was collected by filtration, washed with water, and dried under an infrared lamp. The compound was used without further purification. Yield: 1.5g (45.5%).

According to the analysis of related databases, 19179-31-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xu, Li-Li; Wu, Yu-Feng; Wang, Lei; Li, Cui-Cui; Li, Li; Di, Bin; You, Qi-Dong; Jiang, Zheng-Yu; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 1376 – 1394;,
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Adding a certain compound to certain chemical reactions, such as: 38487-85-3, name is 2-Amino-4-methoxybenzonitrile, 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 38487-85-3, Formula: C8H8N2O

EXAMPLE 28 9-Amino-3,4-dihydro-6-methoxyacridin-1(2H)-one 2-Amino-4-methoxybenzonitrile (7.51 g) was suspended in 75 ml of benzene containing 6.&sl0; g of cyclohexane-1,3-dione and 1.1 g of p -toluenesulfonic acid monohydrate. The reaction mixture was brought to reflux, at which time a homogeneous solution was obtained. After 15 minutes a thick precipitate developed, which was stirred in the refluxing solvent for an additional 15 minutes. At the end of this time thin layer chromatography (TLC, hereafter) showed that the starting material had been consumed, so the precipitate was filtered off, taken up in 2-butanone, and washed with sodium bicarbonate solution. The organic phase was dried and evaporated to a solid, which was triturated with ether to give 1&sl0;.61 g of the enamine, mp 194-196C. This material was suspended in 25&sl0; ml of tetrahydrofuran to which was then added 11.9 g of milled potassium carbonate and &sl0;.85 g of CuCl. The reaction mixture was then refluxed for a total of 48 hours, with additional portions of CuCl (&sl0;.5&sl0; g at a time) added at 6 hour and at 3&sl0; hour. At the end of this time methanol (1&sl0;&sl0; ml) was added to the reaction mixture and reflux was continued for 15 minutes. It was then filtered through diatomaceous earth, evaporated, and purified by flash chromatography (1&sl0;% methanol-dichloromethane). Obtained in this manner was 5.1 g of product that was suitable to be carried on to the next step. A 1.5 g portion was recrystallized from methanol to give 1.12 g of analytically pure material, mp 244-246C.

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; HOECHST-ROUSSEL, PHARMACEUTICALS INCORPORATED; EP179383; (1991); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

50397-74-5, name is 4-Amino-3-bromobenzonitrile, 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. name: 4-Amino-3-bromobenzonitrile

50.0 g (253.76 mmol) of 4-amino-3-bromobenzonitrile, 4-bromobenzoyl chloride 55.7 g (253.76 mmol) of (4-bromobenzoyl chloride) and 500 mL of pyridine were added thereto, followed by stirring at reflux for at least 12 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. Solid to pale yellow by solidification with diisopropyl ether (IPE) 75.6 g (yield: 78.3%) of a mixture (intermediate (12)) was obtained.

The synthetic route of 50397-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Raepto Co., Ltd.; Seok Mun-gi; Go Byeong-su; Im Cheol-su; Kim Hyeon-a; Kim Gyu-sik; Park Yong-pil; Han Gap-jong; Oh Yu-jin; (37 pag.)KR102059550; (2019); B1;,
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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. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 4-(Hydroxymethyl)benzonitrile

To a solution of 7-ethoxy-2,3-dihydro-2,2-dimethyl-alpha-(1-methylethyl)-5-benzofuranmethanol (1.26 g, 4.78 mmol) and 4-cyanobenzenemethanol (530 mg, 3.98 mmol) in toluene (3.5 ml) and acetic acid (2 ml) was added conc. sulfuric acid (0.53 ml, 9.95 mmol), and the mixture was stirred for 1 hour at 80C. Ethanol (35.9 ml) was added dropwise thereto at the same temperature and the mixture was stirred for 30 minutes. After cooling, the reaction mixture was poured into ice water, and washed with diisopropyl ether. The aqueous layer was neutralized with sodium hydrogen carbonate, and extracted three times with ethyl acetate. The combined organic layer was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to a basic silica gel column chromatography (hexane/ethyl acetate, 10:1 followed by 5:1), and crystallized from diisopropyl ether-hexane to give the title compound (614 mg, yield 37%). 1H NMR (CDCl3) delta 1.23 (6H, s), 1.28 (6H, s), 1.46 (3H, t, J = 7.0 Hz), 2.11 (3H, s), 2.20 (2H, s), 2.66 (2H, s), 4.18 (2H, q, J = 7.0 Hz), 5.15 (2H, s), 6.60 (1H, s), 7.34-7.42 (4H, m).

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 874-89-5.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1541576; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 31643-49-9, A common heterocyclic compound, 31643-49-9, name is 4-Nitrophthalonitrile, molecular formula is C8H3N3O2, 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.

To a 500 mL three-neck rounde-bottom flask was added resorcinol (16.52 g, 0.15 mol), 4-nitrophthalonitrile (51.94 g, 0.30 mol) and 180 mL DMSO. During the course of the reaction, the K2CO3 (62.19 g, 0.45 mol) was added in three portions at an interval of 20 min. Then the resulting mixture was heated at 40 C for 12 h under nitrogen. After cooling, the product mixture was poured into water. The light yellow filtrate was collected by suction filtration and washed with large amount of water until the filtrate was neutral. The crude product (42.0 g) was purified by rinsing with CH2Cl2 in Buchner funnel and suction flask, and the filtrate was then dried by evaporation under a vacuum at 80 C for 5 h to remove CH2Cl2. The yellow-white powder was obtained in 68.7 wt% yield (28.9 g), m. p. peak at 183 C (sharp) (DSC) at a heat rate of 10 C/min. FTIR (KBr), 2232 (C?N), 1284 (Ar-O-Ar), 1248 (Ar-O-Ar). 1H NMR (400 MHz, DMSO-d6): 8.14-8.11 (d, 2H; Ar H), 7.92 (s, 2H; Ar H), 7.63-7.53 (m, 3H; Ar H), 7.15-7.12 (m, 3H; Ar H).

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:
Article; Yuan, Ping; Ji, Suchun; Hu, Jianghuai; Hu, Xueping; Zeng, Ke; Yang, Gang; Polymer; vol. 102; (2016); p. 266 – 280;,
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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. 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

. 4-({[2-(methyloxy)phenyI]methyl}amino)-2-(trifluoromethyl)benzonitriIeTo a solution of 4-flouro-2-(trifluouromethyl)benzonitrile (reagent A) (500 mg, 2.6 mmol) in anhydrous DMF (0.5 M) was added 2-methoxybenzylamine (reagent B) (0.35 mL, 2.6 mmol) and oven-dried potassium carbonate (365 mg, 2.6 mmol). The reaction mixture stirred at 85 0C for 18 hours. After cooling to room temperature, the reaction mixture was diluted with water. The organics were extracted into ethyl ether and dried over sodium sulfate. The Filtrate was concentrated, and remaining DMF was removed under reduced pressure to yield a beige solid (415 mg, 51% crude yield): MS (ESI) 306.3 (MH)+.

The synthetic route of 194853-86-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/113552; (2006); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Some common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, molecular formula is C8H3ClF3N, 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: 2-Chloro-4-(trifluoromethyl)benzonitrile

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) and appropriate thiol (RSH, 3.00 mmol),18-crown-6-ether (cat.) and potassium carbonate (2.00 mmol)were dissolved in acetonitrile (3 ml). The mixture was refluxedfor 12 h and then cooled to ambient temperature. The mixturewas quenched by adding water and extracted with EtOAc.Extracted organic compound was dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:4) eluantcondition. (RSH = CH3CO2(CH2)2SH for 42).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1813-33-8, its application will become more common.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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Related Products of 17823-40-4, 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 17823-40-4 as follows.

A mixture of 2-ethynyl-1,3-dimethylbenzene (Compound 6) (0.4 g, 3.0 mmol), 4-bromo-2,3,5,6-tetrafluorobenzonitrile (0.38 g, 1.5 mmol), Pd(PPh3)4 (0.173 g,0.15 mmol), Cul (0.057 g, 0.3 mmol) and diisopropylamine (0.4 g, 4 mmol) in dioxane (40 mL) was degassed and heated at about 80 C for about 16 hours. The resulting mixture was worked up with ethyl acetate. After filtered off precipitate, the solution was loaded on silica gel and purified by flash column using eluents of hexane to hexane/dichloromethane (4:1). Removal of solvent give a white solid (Compound 7) (0.4 g, in 88% yield).

According to the analysis of related databases, 17823-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, SHIJUN; BASIAGO, ADAM; (86 pag.)JP2016/526025; (2016); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 302912-31-8, These common heterocyclic compound, 302912-31-8, name is Ethyl 2-(4-cyanophenyl)-2-oxoacetate, 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 (4-cyano-phenyl)-oxo-acetic acid ethyl ester 1.0 g, 4.9 mmol) in 20 mL of dichloromethane and (diethylamino)sulfur trifluoride (DAST) (1.0 g, 6.2 mmol) was stirred at r.t. for 3 hrs. The mixture was poured into iced water and extracted with ethyl acetate. The organics were dried over MgSO4 and concentrated to give crude (4-cyano-phenyl)-difluoro-acetic acid ethyl ester which was used for the reaction.

Statistics shows that Ethyl 2-(4-cyanophenyl)-2-oxoacetate is playing an increasingly important role. we look forward to future research findings about 302912-31-8.

Reference:
Patent; Wyeth; US2005/131014; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts