Tag: M.W=100-200

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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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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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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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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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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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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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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Reference of 21423-81-4, 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 21423-81-4 as follows.

Example 45 Preparation of 4-(Bromomethyl)-3-chlorobenzonitrile (CI10) To a stirred solution of 3-chloro-4-methylbenzonitrile (5 g, 25.4 mmol) in carbon tetrachloride (CCl4; 50 mL) under an argon atmosphere was added NBS (5.16 g, 29 mmol), and the mixture was degassed for 30 min. To this was added azobisisobutyronitrile (AIBN; 0.3 g, 1.8 mmol), and the resultant reaction mixture was heated at reflux for 4 h. The reaction mixture was cooled to ambient temperature, washed with water, and extracted with CH2Cl2. The combined CH2Cl2 layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The crude compound was purified by flash column chromatography (SiO2, 100-200 mesh; 5% EtOAc in n-Hexane) to afford the title compound as a white solid (4.8 g, 68%): mp 87-88 C.; 1H NMR (400 MHz, CDCl3) delta 7.71 (s, 1H), 7.59 (s, 2H), 4.60 (s, 2H); ESIMS m/z 229.77 ([M+H]+); IR (thin film) 2235, 752, 621 cm-1.

According to the analysis of related databases, 21423-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; Lo, William C.; Hunter, James E.; Watson, Gerald B.; Patny, Akshay; Iyer, Pravin S.; Boruwa, Joshodeep; US9211280; (2015); B2;,
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Reference of 6393-40-4,Some common heterocyclic compound, 6393-40-4, name is 4-Amino-3-nitrobenzonitrile, molecular formula is C7H5N3O2, 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 solution of 4-amino-3-nitrobenzonitrile (1) (3.0 g) in ethanol (80 mL) was sparged for 5 minutes with nitrogen. Palladium on carbon (10%, 300 mg) was added and the mixture was saturated with hydrogen. The mixture was stirred under a hydrogen balloon for seven hours. The mixture was sparged with nitrogen and filtered through celite. The filtrate was concentrated in vacuo to provide the title compound, 3,4- diaminobenzonitrile (2).

The synthetic route of 6393-40-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACOPEIA , INC.; WO2008/60301; (2008); A1;,
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Related Products of 39581-21-0, The chemical industry reduces the impact on the environment during synthesis 39581-21-0, name is N-Butyl-2-cyano-acetamide, I believe this compound will play a more active role in future production and life.

General procedure: To a stirred solution of the cyanoacetamide (2.0mmol) in EtOH (3mL), the ketone or aldehyde (2.0mmol) was added and dissolved. Then, triethylamine (Et3N) (2.0mmol) and S8 (0.25mmol) were added and the reaction mixture was refluxed overnight. Afterwards, it was diluted with EtOAc (25mL) and washed with water (2¡Á25mL) and brine (2¡Á25mL). The combined organic layers were dried over MgSO4, filtrated and the solvent was removed under reduced pressure. Further purification by flash chromatography, with heptane:EtOAc 3:1 (v/v) as eluent, was performed when needed.

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, N-Butyl-2-cyano-acetamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Eleftheriadis, Nikolaos; Poelman, Hessel; Leus, Niek G.J.; Honrath, Birgit; Neochoritis, Constantinos G.; Dolga, Amalia; Doemling, Alexander; Dekker, Frank J.; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 786 – 801;,
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