Month: February 2021

Application of 52805-37-5, A common heterocyclic compound, 52805-37-5, name is 3-(Benzyloxy)-4-methoxybenzonitrile, molecular formula is C15H13NO2, 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.

Example 11Preparation of 5-(benzyloxy)-4-m ethoxy-2-n itrobenzonitri le (IV)[0042] Under N2 (g), HNO3 (65%, 84 mL) was cooled to 0-5C. To a solution of 3-(benzyloxy)-4-methoxybenzonitrile (III, 14.0 g, 58.6 mmol, 1.0 eq.) in acetic acid (33.6 mL, 2.4 P) was added dropwise at 0-10C and after the addition the temperature was allowed to warm to 20-25 C. After the reaction completion, ice-water (150 mL, 10.7 P) was added to the mixture. The mixture was filtered, washed with water (30 mL x2) and dried in vacuo at 50C to give desired 5-(benzyloxy)-4-methoxy-2-nitrobenzonitrile (IV, 13.5 g) in 85% yield.1H NMR (400 MHz, CDCI3) O 7.80 (5, 1 H), 7.43-7.37 (m, 5H), 7.24(s, 1 H), 5.25(s, 2H),4.03 (5, 3H).l3 NMR (100MHz, CDCI3) O 152.70, 152.50, 142.91, 134.45, 129.00 (2C), 128.88,127.47 (2C), 117.13, 115.50, 108.17, 100.65, 56.85.

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; SCINOPHARM (CHANGSHU) PHARMACEUTICALS, LTD.; ZHANG, Xiaoheng; LV, Xizhou; WO2015/188318; (2015); 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. 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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Synthetic Route of 1813-33-8, A common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, molecular formula is C8H3ClF3N, 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 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol), appropriate amine (NR2, 2.00 mmol),and DBU (2.5 mmol) were dissolved in 1,4-dioxane (8 ml). Themixture was stirred for 12 h at 50 C. The reaction was quenched with water and extracted with EtOAc twice. The combined organicextracts were dried over MgSO4, filtered, and concentrated invacuo. The residue was purified by flash column chromatographyon silica gel using EtOAc/hexane (1:7-1:10) eluant condition.(NR2 = 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloridefor 17).

The synthetic route of 1813-33-8 has been constantly updated, and we look forward to future research findings.

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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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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Related Products of 20099-89-2, These common heterocyclic compound, 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, 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 a mixture of olefin (0.5 mmol) and tween-80 (30 mL) in water (3 mL) was added DBH (214.5 mg, 0.75 mmol) at room temperature, and the mixture was stirred under the conditions as indicated in Table 1. After cooling to room temperature and removal of solvent under reduced pressure, EtOH (3 mL), thiourea (57.1 mg, 0.75 mmol) (or 0.75 mmol of N-methylthiourea/N-phenethylthiourea) were added to the mixture, and the obtained mixture was stirred for 2 h at 80 C. The mixture was diluted with ethyl acetate (60 mL). The organic phase was washed with brine (10mL x 3) and dried over Na2SO4. After concentrated under reduced pressure, the residue was purified by preparative thin layer chromatography to afford the corresponding 2-aminothiazoles.

Statistics shows that 4-(2-Bromoacetyl)benzonitrile is playing an increasingly important role. we look forward to future research findings about 20099-89-2.

Reference:
Article; Ma, Chunhua; Miao, Yuqi; Zhao, Minghao; Wu, Ping; Zhou, Jianglu; Li, Zhi; Xie, Xilei; Zhang, Wei; Tetrahedron; vol. 74; 27; (2018); p. 3602 – 3607;,
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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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Reference of 425379-16-4, A common heterocyclic compound, 425379-16-4, name is 2-Bromo-3-fluorobenzonitrile, molecular formula is C7H3BrFN, 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.

Step 3. 2′,6-Difluoro-5 ‘-(5 -(2-hydroxy- 1.1.1,3.3.3 – c -propan-2- ylV 1 H- benzo 1imidazol-l-yl biphenyl-2-carbonitrile (108): A mixture of lOu (1.7 g, 4.78 mmol), bis(pinacolato)diboron (1.47 g, 5.8 mmol) and KOAc (1.18 g, 12.0 mmol) in dioxane (30 mL) was purged with nitrogen for 5 minutes. Bis(triphenylphosphine)palladium(II)- dichloride (270 mg, 0.38 mmol) was added and the mixture was heated at 120 C overnight. The mixture was diluted with EtOAc (200 mL) and the solution was washed with water (2 x 30 mL) and brine, then dried (Na S04). After concentrating to dryness the material was dissolved in MeOH (30 mL) and concentrated to dryness again. The concentration step from MeOH was repeated a total of five times until about 2.1 g of a tan colored solid was obtained. This intermediate (2.1 g) was stirred in THF (20 mL) and water (10 mL) and was treated with 3-fluoro-2-bromo-l-cyanobenzene (1.2 g, 6 mmol) and K2C03 (1.5 g, 10.8 mmol). The mixture was purged with nitrogen for five minutes, then bis(di-t-butylphosphine) ferrocene palladium(II)dichloride (130 mg, 0.2 mmol) was added. The solution was heated at 60 C overnight. The cooled mixture was diluted with EtOAc (120 mL) and washed with water (30 mL). The organic phase was dried (Na2S04) and concentrated. The crude product was purified on an Analogix automated chromatography system eluting with 0-3% MeOH/CH2Cl2. The partially purified mixture was further purified on a reverse-phase CI 8 column eluting with 0-50% acetonitrile/water. The purest fractions were collected and concentrated to remove acetonitrile and the solid was isolated by filtration. This solid was passed through a short silica gel column eluting with 3% MeOH/CH2Cl2 to give 320 mg (17%) of 108 with 99.8% purity. 1H-NMR (300 MHz, CDC13): delta 1.89 (s, 1H), 7.42-7.44 (m, 0.19H), 7.45-7.47 (m, 0.65H), 7.47-7.50 (m, 0.76H), 7.51 (app d, J= 1.46, 0.33H), 7.53-7.67 (m, 6H), 7.99 (dd, J= 0.7, 1.7, 1H), 8.12 (s, 1H). 13C-NMR (75 MHz, CDC13): delta 109.95, 116.31, 117.79, 118.11, 120.75, 121.05, 121.32, 127.03, 127.15, 127.38, 129.32, 129.37, 131.15, 131.27, 132.53, 142.47, 143.92, 144.65, 158.05, 161.41. HPLC (method: Waters Atlantis T3 2.1 column 2.1 x 50 mm 3mu?iota – gradient method 5-95% ACN + 0.1% formic acid in 14 min with 4 min hold at 95% ACN+0.1% formic acid; wavelength: 305 nm):retention time: 5.85 min; 99.8% purity. MS (M+H): 396.3. Elemental Analysis(C^HnDgFa^O): Calculated: C=69.87, H=4.33, F=9.61, N=10.63. Found: C=79.27, H=4.05, F=9.63, N=10.53.

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; CONCERT PHARMACEUTICALS, INC.; LIU, Julie, F.; HARBESON, Scott, L.; WO2011/47315; (2011); A1;,
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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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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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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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