Month: February 2021

Related Products of 6629-04-5, A common heterocyclic compound, 6629-04-5, name is N-Cyanoacetylurethane, molecular formula is C6H8N2O3, 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.

General procedure: To the mixture of substituted anilines (0.08mol), concentrated hydrochloric acid (45.0mL) and water (120.0mL), aqueous solution of NaNO2 (60.0mL, 0.11mol) was added drop-wise under stir at a rate that the temperature below 0C, and the reaction mixture was stirred for 0.5h. A mixture of ethyl (2-cyanoacetyl)carbamate (13.7g, 0.09mol) and sodium acetate (24.0g, 0.27mol) in ethanol (400.0mL) was added drop-wise to the resulting diazonium salt solution below 0C and stirred for a further 2h. The precipitate was collected by filtration and washed with water (40.0 mL¡Á2), dried to give compounds 7a-f.

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; Zhao, Sijia; Zhang, Yu; Zhou, Hongyang; Xi, Shuancheng; Zou, Bin; Bao, Guanglong; Wang, Limei; Wang, Jiao; Zeng, Tianfang; Gong, Ping; Zhai, Xin; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 37 – 50;,
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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. 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H4N4

General procedure: Et3N (0.3 mmol) was added to a stirred solution of salicylaldehyde (3 mmol), 2-aminoprop-1-ene-1,1,3-tricarbonitrile (3 mmol) and 3-trifluoromethyl-2-pyrazolin-5-one in 5 ml of n-PrOH at ambient temperature. Then mixture was refluxed for 4 h. After the reaction was finished and cooled the solid was filtered and dried to isolate pure substituted 2,4-diamino-5-(5-hydroxy-3-(trifluoromethyl)-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile. In some cases cristallisation from EtOH-DMSO is needed.

According to the analysis of related databases, 868-54-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Elinson, Michail N.; Vereshchagin, Anatoly N.; Anisina, Yuliya E.; Fakhrutdinov, Artem N.; Goloveshkin, Alexander S.; Egorov, Mikhail P.; Journal of Fluorine Chemistry; vol. 213; (2018); p. 31 – 36;,
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501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, 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: 2-(3-Fluorophenyl)acetonitrile

The reactor was charged with palladium(II) acetate (0.160 g, 0.71 1 mmol), 2,8,9-triisobutyl- 2,5,8,9-tetraaza-l-phosphabicyclo[3.3.3]undecane (0.507 mL, 1.421 mmol), and 5-bromo-2- methyl- lH-benzo[d]imidazole (1.5 g, 7.1 1 mmol). The vessel was evacuated and refilled with N2 for 3 cycles and degassed dioxane (14.21 mL) was added, followed by NaHMDS (28.4 mL, 28.4 mmol). The reaction was stirred at 25C for 20 min before 2-(3-fluorophenyl)acetonitrile (73.3 mg, 0.543 mmol) was added. The reaction was then capped and heated at 100C for 3 h. More NaHMDS (6 mL) was added and the reaction was stirred for another 1 h; More NaHMDS (4 mL) was added and the reaction was stirred for another 1 h before it was cooled to room temperature, and quenched with water. The aqueous layer was extracted with EtOAc (3x), washed with brine, dried over MgS04, filtered, and the filtrate was concentrated in vacuo. The crude material was purified by chromatography on silica gel (eluent: 0-100% A in B. A: 10% MeOH in DCM; B: DCM.). LCMS calc. = 266.10, found = 266.04 (M+H)+.

The synthetic route of 501-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MOCHIDA PHARMACEUTICAL CO., LTD.; ZHANG, Ting; CHEN, Yi-Heng; GUO, Liangqin; HRUZA, Alan; JIAN, Tianying; LI, Bing; MENG, Dongfang; PARKER, Dann, L., Jr.; SHERER, Edward, C.; WOOD, Harold, B.; SAKURADA, Isao; (130 pag.)WO2016/94260; (2016); A1;,
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Electric Literature of 53312-80-4, 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. 53312-80-4, name is 4-Amino-2-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The compound from step 4 (0.3 g, 0.96 mmol) was dissolved in DMF (4.83 ml), 4-cyano-3-fluoroaniline (0.131 g, 1 eq) and NaH (0.155 g of 60% dispersion in mineral oil, 4 eq) were added. After 1 hour LCMS showed complete conversion, the reaction was quenched with NH4CI(Sat) and extracted with EtOAc. The extracts were dried concentrated and the residue purified by silica gel chromatography (0-20% EtOAc in hexane) to give 0.3 g of the title compound. LCMS MH+ = 411.

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-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SCHERING CORPORATION; CHELLIAH, Mariappan, V.; CHACKALAMANNIL, Samuel; GREENLEE, William, J.; EAGEN, Keith, A.; GUO, Zhuyan; CLASBY, Martin, C.; XIA, Yan; JAYNE, Charles, L.; DWYER, Michael; KEERTIKAR, Kartik, M.; CHAN, Tin-Yau; WANG, Li; WO2011/17296; (2011); A1;,
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Reference of 939-80-0,Some common heterocyclic compound, 939-80-0, name is 4-Chloro-3-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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.

The starting material was prepared as follows: Diethyl malonate (44.6ml, 293 mmol) was added dropwise over 1.5 hours to a suspension of sodium hydride (11.7 g of a 60% suspension in mineral oil, 293 mmol) in DMF under argon and the reaction mixture was stirred at ambient temperature for 30 minutes. The resulting solution was added dropwise over 1 hour to a solution of 2-chloro-5-cyano-1-nitrobenzene (24.3 g, 133 mmol) in DMF (75 ml) cooled with a dry ice/acetone bath. The temperature of the cooling bath was adjusted to prevent the freezing of the red reaction mixture. After the addition was completed, the reaction was left to rise to ambient temperature over 2 hours. The resulting red solution was poured slowly into a stirred mixture of ice (100 ml) and 1M hydrochloric acid (10 ml). The resulting yellow precipitate was collected by filtration, washed with water until the filtrate was at pH7.0 and then dried under vacuum to give diethyl (4-cyano-2-nitrophenyl)malonate (39.6 g, 97%).

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

Reference:
Patent; Zeneca Limited; US6265411; (2001); B1;,
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Adding a certain compound to certain chemical reactions, such as: 21667-62-9, name is 3-(3-Chlorophenyl)-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 21667-62-9, category: nitriles-buliding-blocks

To 3-chlorobenzoylacetonitrile (24,360 mg, 2 mmol) and sulfur (76 mg) in [DUT] [(4] mL), triethylamine (0. [25ML)] is added under stirring. To this solution [TETRAHYDROTHIOPYRAN-4-ONE] (11,232 mg, 2 mmol) is added dropwise. The mixture is stirred for 16 hours and it is poured into water (30 [ML),] which is extracted with diethyl ether (30 mL). The ethereal solution is dried with sodium sulfate and concentrated to give the desired compound as an orange solid (373 mg, [78%).] Physical characteristics: MS [(ES+)] for [M/Z] 294,296 (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; PHARMACIA & UPJOHN COMPANY; WO2004/35591; (2004); A1;,
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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. 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-2-methylbenzonitrile

[ TERT-BUTYL 4- (4-CYANO-3-METHYLPHENYL)-3, 6-DIHYDROPYRIDINE-1 (2H)-CARBOXYLATE] [4-BROMO-2-METHYL-BENZONITRILE] (150 mg, 0.77 mmol), tert-butyl [4- (4,] 4, [5,] 5-tetramethyl- 1, 3, 2-dioxaborolan-2-yl)-3, [6-DIHYDROPYRIDINE-1] [(2H)-CARBOXYLATE] (284 mg, 0.92 mmol) and [PDCL2] (dppf) (38 mg, [0.] 05 mmol) were dissolved in toluene (2. [5] ml), [ETOH] (0.75 ml) and 2M aqueous [NA2CO3.] The reaction vessel was purged with nitrogen and heated at [80 C] over night. After cooling, the mixture was partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over [NA2SO4] and purified using flash chromatography (heptane: [ETHYLACETATE] 7: 1) affording 171 mg (74%) of white crystals. [LC-MS M/Z 199 [M+].] IH NMR [(CDCI3)] : [8] 7.52 [(1H,] d, J=8. 09 Hz); 7.27 [(1H,] s); 7.23 [(1H,] d, [J=8.] 51 Hz); 6.12 [(1H,] bs); 4.07 (2H, q, J=5. 81 Hz); 3.61 (2H, t, J=5. 61 Hz); 2.52 (3H, s); 2.48 (2H, bs); 1.47 (9H, s).

The synthetic route of 67832-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WO2004/24718; (2004); A1;,
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Reference of 179897-89-3, These common heterocyclic compound, 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, 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.

General procedure: A mixture of compound 1 (5.0 mmol), alkylamine (15.0 mmol),and K2CO3 (15.0 mmol) in DMF (10 mL) was reacted at 70e80 C for3e5 h. After the reaction was complete, the mixture was pouredinto H2O (100 mL) and extracted with ethyl acetate (100 mL 2).The organic layer was collected, washed with brine (100 mL 3),dried over anhydrous Na2SO4, and concentrated under vacuum toyield the crude product, which was purified by flash columnchromatography (0e15% ethyl acetate in petroleum ether).

The synthetic route of 179897-89-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Haiyan; Li, Xiaolei; Li, Yuanyuan; Zhu, Xinying; Zhang, Lei; Li, Jing; European Journal of Medicinal Chemistry; vol. 186; (2020);,
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Adding a certain compound to certain chemical reactions, such as: 1194-02-1, name is 4-Fluorobenzonitrile, 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 1194-02-1, Formula: C7H4FN

General procedure: Triethylamine (42 mL, 0.3 mol) was added to a solution of benzonitrile (21, 10.3 g, 0.1 mol), hydroxylamine hydrochloride (20.9 g, 0.3 mol) and ethanol (150 mL) and stirred for 12 h at 75 C. The reaction mixture was cooled to room temperature and evaporated to dryness, extracted with DCM (300 mL)/water (100 mL). The organic layer dried with MgSO4, filtered and evaporated to dryness yielding the desired product 22 as a primrose yellow liquid (10.6 g, yield 78%). 1H NMR (300 MHz, DMSO-d6): delta = 9.59 (s, 1H), 7.62-7.67 (m, 2H), 7.32-7.37 (m, 3H), 5.77 (s, 2H); LC/MS (ESI): m/z 137 [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:
Article; Xia, Guangxin; You, Xiaodi; Liu, Lin; Liu, Haiyan; Wang, Jianfa; Shi, Yufang; Li, Ping; Xiong, Bing; Liu, Xuejun; Shen, Jingkang; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 1 – 10;,
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Electric Literature of 96784-54-2, A common heterocyclic compound, 96784-54-2, name is 3-Methyl-4-nitrobenzonitrile, 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.

A. 4-Amino-3-methyl benzonitrile To a solution of 3-methyl-4-nitrobenzonitrile (2.0 g, 12.3 mmol) in 100 mL of EtOH is added SnCl2 (13.9 g, 61.7 mmol). The resulting solution is heated at reflux. After 2 h, the solution is cooled to ambient temperatures. The solution is poured into 150 mL of ice water. The pH of the solution is adjusted to >7 with a solution of saturated NaHCO3. The solution is diluted with EtOAc and the resulting mixture is filtered through Celite. The filtered solution is separated. The organic layer is dried over MgSO4, filtered and concentrated to give the title compound (1.57 g, 8.7 mmol) as an off-white solid. 1 H NMR (CDCl3, 300 MHz) delta7.30 (m, 2H), 6.63 (d, 1H), 4.10 (bs, 2H), 2.15 (m, 2H). EI MS, [M]+ =132.

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; Rhone-Poulenc Rorer Pharmaceuticals Inc.; US5731315; (1998); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts