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. 4110-35-4, name is 3,5-Dinitrobenzonitrile, A new synthetic method of this compound is introduced below., Safety of 3,5-Dinitrobenzonitrile

Example 19 – Preparation of 3-Amino-5-[(7-chloroquinolin-4-yl)amino] benzonitrile hydrochloride (compound 73); Step A: 3,5-Diaminobenzonitrile; To 3,5-dinitrobenzonitrile (5.0 g, 25.89 mmol) in 20 mL of HCI 1 M, was added SnCI2 (34.4 g, 7 eq). The reaction mixture was stirred at room temperature for 2h and then cooled to O’C. The mixture was made alkaline with a 50% aqueous solution of NaOH and the precipitate was removed by filtration. The filtrate was extracted with ethyl acetate and the combined organic layers were evaporated. The residue and the precipitate were purified by flash chromatography on silica gel (DCM/MeOH//95/5) to yield expected compound as an orange solid (1 .95 g, 57% yield), m/z (ESI) 134.0 [M+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:
Patent; INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM); UNIVERSITE LILLE 2 DROIT ET SANTE; DELACOURTE, Andre; MELNYK, Patricia; BURLET, Stephane; LEFUR, Nicolas; WO2011/73322; (2011); A1;,
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Reference of 4513-77-3, The chemical industry reduces the impact on the environment during synthesis 4513-77-3, name is 2-Oxocyclohexanecarbonitrile, I believe this compound will play a more active role in future production and life.

General procedure: The corresponding 2-hydrazino-benzoic acid or methyl-2-hydrazinobenzoate (1.1 mmol) and the alpha-oxo-cyano compound (1 mmol) were suspended in dry ethanol (5.5 ml) and refluxed for 3 h. After cooling, the product was precipitated, filtered, and dried in vacuo to yield the title products.

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

Reference:
Article; Kovacs, Daniel; Molnar-Toth, Judit; Blasko, Gabor; Fejes, Imre; Nyerges, Miklos; Synthetic Communications; vol. 45; 14; (2015); p. 1675 – 1680;,
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Application of 77532-79-7,Some common heterocyclic compound, 77532-79-7, name is 5-Fluoro-2-methylbenzonitrile, molecular formula is C8H6FN, 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.

2-(Bromomethyl-5-fluorobenzonitrile. N2 was passed through a mixture of 5-fluoro-2-methylbenzonitrile (28.51 g, 211 mmol), NBS (41.31 g, 232 mmol) and AIBN (2.5 g, 15 mmol) in CCl4 (845 mL) for 10 min after which the reaction was heated at reflux for 8 h. After standing at room temperature overnight, the reaction mixture was filtered and the filter cake washed with CCl4 (500 mL). The combined filtrate was evaporated to give a yellow oil. Flash chromatography (SiO2) using 5-25% ethyl acetate/Hexanes as eluent afforded the title compound (29.74 g, 66% yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) delta: 7.55 (1H, dd, J=8.6, 5.2 Hz), 7.37 (1H, dd, J=7.9, 2.8 Hz), 7.32-7.28 (1H, m), 4.61 (2H, s).

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

Reference:
Patent; Bristol-Myers Squibb Company; US2007/129379; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 6629-04-5, name is N-Cyanoacetylurethane, 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 6629-04-5, Application In Synthesis of N-Cyanoacetylurethane

Take 15.0 of aniline, 90mL of concentrated hydrochloric acid, and 200mL of water to dissolve it.The solution is cooled below 0 C,A 70 mL aqueous solution containing 13.4 g of sodium nitrite was added dropwise,During the dropwise addition, keep the temperature below 0 C. After the dropwise addition is completed, keep warm and stir for 0.5h.Add 400 mL of ethanol to dissolve2-cyano-2-acetyl urethane 26.4gIt was incubated with a mixture of anhydrous sodium acetate 39.7 for 3 h.The solid precipitated in the reaction mixture was filtered, and the filter cake was washed with water.dryGot a pale yellow product,Intermediate[2-cyano-2- (2-phenylhydradino) acetyl] urethane(h).

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

Reference:
Patent; Liaoning University; Liu Ju; Chen Ye; Li Chunyan; Ding Shi; Gong Yilin; Shi Jiantao; Hao Xuechen; Wang Zhen; Yang Yaxing; (23 pag.)CN110684013; (2020); A;,
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Synthetic Route of 6136-68-1, 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. 6136-68-1, name is 3-Acetylbenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Part A. Preparation of ethyl 3-(3-cyanophenyl)-3-oxopropionate. To a suspension of sodium hydride (1.2 g of 60% suspension in mineral oil, hexane-washed, 30.3 mmol) in 40 mL of tetrahydrofuran was added diethyl carbonate (3.7 mL, 30.3 mmol) and 3-acetyl benzonitrile (2.2 g, 15.2 mmol). The resulting suspension was stirred at 65 C. for 1 h and then was cooled to room temperature. There was added 40 mL of 10% aqueous HCl and the reaction mixture was diluted with ethyl acetate and the layers were separated. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to afford 3.2 g (96%) of the title compound, which was sufficiently pure to be used without purification. MS (NH3-CI) 218.3 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis 3-Acetylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Dupont Pharmaceuticals Company; US6187797; (2001); B1;,
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Application of 3215-64-3, A common heterocyclic compound, 3215-64-3, name is 2-(2,6-Dichlorophenyl)acetonitrile, molecular formula is C8H5Cl2N, 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.

[0494] To a solution of (2,6-dichlorophenyl)acetonitrile (1.00 g, 5.38 mmol) in THF (8 ml) under argon was added gradually while stirring, at -78C., a 2 M solution of LDA in THF (4.0 ml, 8.1 mmol). The mixture was allowed to come to 0C. and, after 15 min, cooled back down again to -78C. Subsequently, tert-butyl bromoacetate (1.2 ml, 8.1 mmol) was slowly added dropwise with stirring. The cooling bath was removed and, with stirring, the mixture was allowed to warm to RT overnight. Subsequently, water was added gradually to the mixture, which was extracted twice with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue was taken up in dichloromethane and purified by flash column chromatography (100 g silica gel Biotage Snap-Cartridge KP-Sil, cyclohexane/ ethyl acetate 97:3?8:2, Isolera One). This gave 682 mg (98% purity, 41% of theory) of the title compound. [0495] LC-MS (Method 1): Rt=2.17 min; MS (ESIpos): m/z=300 [M+H]+ [0496] 1H-NMR (500 MHz, DMSO-d6) delta [ppm]: 0.933 (1.68), 0.946 (1.79), 1.363 (16.00), 1.392 (2.64), 1.401 (1.37), 3.025 (0.58), 3.038 (0.57), 3.181 (0.57), 3.198 (0.58), 3.315 (0.99), 7.461 (0.61), 7.463 (0.68), 7.478 (0.76), 7.582 (2.03), 7.598 (1.5).

The synthetic route of 3215-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; Bayer Pharma Aktiengeseiisehaft; BECK, Hartmut; KAST, Raimund; MEININGHAUS, Mark; DIETZ, Lisa; FUERSTNER, Chantal; STELLFELD, Timo; ANLAUF, Sonja; VON BUEHLER, Clemens-Jeremias; BAIRLEIN, Michaela; ANLAHR, Johanna; MUENSTER, Uwe; TERJUNG, Carsten; JOERISSEN, Hannah; HAUFF, Peter; MUELLER, Joerg; DROEBNER, Karoline; NAGEL, Jens; (220 pag.)US2020/31775; (2020); A1;,
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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 14447-18-8 as follows. COA of Formula: C10H9NO2

In a 500 mL three-neck flask reactor equipped with a thermometer,Benzyl cyanoacetate 63 mL (0.5 mol) was added,Pyridine 10mL,N-octadecyl-3-aminoacrolein42mL (0.25mol),Place the prepared device in the microwave.Set microwave radiation conditions, 35C temperature,The microwave power is 20W and the frequency is 2450MHz.TLC test (petroleum ether:dichloromethane 1:2 development, sublimation iodine coloration) N-octadecyl-3-aminoacrolein reaction was complete, cooled to room temperature, HCl gas was introduced, and the reaction was continued under microwave irradiation ,HPLC followed the reaction until the reaction was over. Add concentrated ammonia to adjust the pH = 5-6, liquid,The aqueous layer was extracted with 1,2-dichloroethane (20 mL¡Á3 times), and the organic layers were combined and washed with water.The solvent 1,2-dichloroethane was distilled off under reduced pressure to obtain 2-chloronicotinic acid benzyl ester.The yellowish liquid was 59.1 g, and the yield was 95.4%.

According to the analysis of related databases, 14447-18-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shandong Normal University; Liu Yufa; Li Dechao; Gu Qiaolian; Sun Lin; Xu Jun; Zhao Jianxia; Cheng Guiying; (11 pag.)CN104945316; (2018); B;,
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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. 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 118431-88-2

General procedure: Under argon atmosphere, the corresponding beta-ketonitrile 2(1 mmol), water (3 mL), the ruthenium(II) complex 1 (0.028 g,0.05 mmol; 5 mol%) and NaO2CH (1.360 g, 20 mmol) were introducedinto a Teflon-capped sealed tube, and the reaction mixturestirred at 100 C for 24e48 h. The solvent was then removed undervacuum and the resulting solid residue purified by flash columnchromatography over silica gel using, unless otherwise stated, amixture of MeOH/EtOAc (1:10) as eluent. Characterization data forthe isolated beta-hydroxyamides are as follows:

According to the analysis of related databases, 118431-88-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Gonzalez-Fernandez, Rebeca; Crochet, Pascale; Cadierno, Victorio; Journal of Organometallic Chemistry; vol. 896; (2019); p. 90 – 101;,
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115279-57-7, name is 2-(4-Aminophenyl)-2-methylpropanenitrile, 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. COA of Formula: C10H12N2

Example 24; l-[4-(Cyano-dimethyl-methyl)-phenyl]- 3-{4-[2-(3-Hydroxy-propylamino)- pyrimidin-4-yloxy] -phenyl} -urea188 mg (1.16 mmol) lJ’-Carbonyl-diimidazol (CDI) were given to a solution of 175 mg (1.09 mmol) 4-(cyano-dimethyl-methyl)-phenylamine (Hicks, T.A., J. Med. Chem. 22 (1979) 1460-1464) in 4.0 ml dichloro-methane and stirred for 12 h.A solution of 284 mg (1.09 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2- ylamino]-propan-l-ol in 6 ml dichloromethane was added within 30 min. and the mixture stirred for 12 h at r.t. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel (ethyl acetate). The obtained material was left overnight with dichloromethane, the precipitate filtered, washed with ether and dried. Yield: 180 mg (37%) of the title compound. MS: 447.58 (ESI+).eta-NMR(400Hz, [DJDMSO): delta = 1.59(br, 2H, CH2-CH2-CH2), 1.67(s, 6H, CH3), 3.22(br, 2H, CH2-NH), 3.38(br, 2H, CH2-OH), 4.37(br, IH, OH), 6.05(br, IH, 5- H-pyrimidine), 7.05(br, IH, CH2NH), 7.09(d, 2H, 3-H/5-H-Ar-NH), 7.41 (d, 2H,Ar-C-CN), 7.49(m, 4H, 2-H/6-H-Ar-NH, Ar-C-CN), 8.12(d, IH, 6-H-pyrimidine), 8.75(s, IH, urea-NH), 8.79(s, IH, urea-NH).

The synthetic route of 115279-57-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2008/77548; (2008); 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. 1441723-24-5, name is 4-Amino-2-fluoro-5-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Amino-2-fluoro-5-methoxybenzonitrile

General procedure: In a sealed vial, i-(benzenesulfonyl)-6-chloro-indole-3-sulfonyl chloride XII-19 (i92 mg, 0.49 mmol) was dissolved in pyridine (4 mL) under argon. 2,i,3-benzoxadiazol-5-amine(i35 mg, i mmol) was added and stirred at room temperature overnight. The reaction mixture was evaporated to dryness then the residue was taken into DCM. The organic phase was washed with HCI i N and brine, dried over Mg504 and evaporated. The dark oil residue solidified on standing and was then triturated in ACN/water (8/2), sonicated and filtered, washed with water and dried under vacuum to provide i70 mg of ii(benzenesulfonyl)-N-(2,i ,3-benzoxadiazol-5-yl)-6-chloro-indole-3-sulfonamide 1-201 a as a yellow solid.Yield: 7i%.Basic LCMS Method i (ES-): 487 (M-H)-, iOO % purity.1H NMR (400 MHz, DMSO-d6)oe ii.52(s, iH), 8.99(s, iH), 8.i6-8.iO (m, 2H), 7.98(d, J= i .8 Hz, i H), 7.9i (dd, J = 9.i, 3.2 Hz, 2H), 7.63 (t, J = 7.5 Hz, i H), 7.56 – 7.5i (m, 2H),7.43 – 7.36 (m, 2H), 7.25 (dd, J = 9.6, i .9 Hz, i 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:
Patent; UCB PHARMA GMBH; MUELLER, Christa E.; PEGURIER, Cecile; DELIGNY, Michael Louis Robert; EL-TAYEB, Ali; HOCKEMEYER, Joerg; LEDECQ, Marie; MERCIER, Joel; PROVINS, Laurent; BOSHTA, Nader M.; BHATTARAI, Sanjay; NAMASIVAYAM, Vigneshwaran; FUNKE, Mario; SCHWACH, Lukas; GOLLOS, Sabrina; VON LAUFENBERG, Daniel; BARRE, Anais; (493 pag.)WO2018/122232; (2018); A1;,
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