Tag: M.W=100-200

Application of 63069-50-1, 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 63069-50-1 as follows.

4-Amino-3-chloro-5-fluorobenzonitrile A mixture of 4-amino-3-fluorobenzonitrile (1 equiv.) and N-chlorosuccinimide (1.5 equiv.) in acetonitrile (0.24 M) was stirred at 85 C. for 5 h. The solvent was removed by concentration and the residue was partitioned between ethyl acetate and 5% NaOH. The organic phase was washed with 5% NaOH and brine. Then the organic phase was dried over MgSO4 and dried in vacuum to afford 4-amino-3-chloro-5-fluorobenzonitrile (88%) as a beige solid. 1H NMR (400 MHz, CDCl3) delta ppm: 7.41 (t, J=6 Hz, 1H), 7.24 (dd, J=1.8, 10.2 Hz, 1H), 4.66 (s, 2H).

According to the analysis of related databases, 63069-50-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Signal Pharmaceuticals, LLC; Alexander, Matthew; Bahmanyar, Sogole; Hansen, Joshua; Huang, Dehua; Hubbard, Robert; Jeffy, Brandon; Leisten, Jim; Moghaddam, Mehran; Raheja, Raj K.; Raymon, Heather; Schwarz, Kimberly; Sloss, Marianne; Torres, Eduardo; Tran, Tam Minh; Xu, Shuichan; Zhao, JingJing; Boylan, John Frederick; (317 pag.)US2016/96841; (2016); 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. 621-50-1, name is 2-(3-Nitrophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Product Details of 621-50-1

To a solution of 3 (400.0 mg, 2.47 mmol) in anhydrous THF (5 mL) was slowly added a suspension of 60% sodium hydride in mineral oil (641.4 mg, 16.03 mmol) in anhydrous THF (4.2 mL) under argon at 0 C. Methyl iodide (1.23 mL, 19.74 mmol) was added to the mixture. The temperature was allowed to rise to room temperature and stirred for 16 h. After being quenched by the addition of water, the aqueous layer was extracted with EtOAc (2 ¡Á 15 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 5:95 to 10:90) to afford 4 (141.3 mg, 30%) as a brown solid; 1H NMR (CDCl3, 400 MHz) 8.31 (1 H, t, J = 2.3 Hz), 8.21-8.19 (1 H, m), 7.90-7.87 (1 H, m), 7.61 (1 H, t, J = 7.8 Hz), 1.79 (6 H, s); 13C NMR (CDCl3, 100 MHz) 148.5, 143.5, 131.6, 130.1, 123.3, 123.0, 120.1, 37.1, 28.9.

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; Suebsuwong, Chalada; Pinkas, Daniel M.; Ray, Soumya S.; Bufton, Joshua C.; Dai, Bing; Bullock, Alex N.; Degterev, Alexei; Cuny, Gregory D.; Bioorganic and Medicinal Chemistry Letters; vol. 28; 4; (2018); p. 577 – 583;,
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Adding a certain compound to certain chemical reactions, such as: 3759-28-2, name is 2-(Cyanomethyl)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 3759-28-2, name: 2-(Cyanomethyl)benzonitrile

General procedure: A mixture of 1-aryl/alkyl-3,3-bis-methylsulfanyl-propenone (1.0 mmol), 2-cyanomethyl-benzonitrile (1 mmol, 142.0 mg), and powdered KOH (2 mmol, 112.0 mg) in dry DMSO (5 mL) was stirred at room temperature for 2 h. Completion of reaction was monitored by TLC. After completion, reaction mixture was poured onto ice-water with constant stirring and then neutralized with 10% HCl. The precipitate obtained was filtered, washed with water and dried over dry sodium sulfate. Many compounds were purified by recrystallization in dry methanol. Some compounds were purified through column chromatography using 15% ethylacetate in hexane as an eluent. Characterization data for some of the synthesized compounds are reported earlier.17

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(Cyanomethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Singh, Surjeet; Althagafi, Ismail; Yadav, Pratik; Panwar, Rahul; Kumar, Abhinav; Pratap, Ramendra; Tetrahedron; vol. 70; 46; (2014); p. 8879 – 8884;,
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Some common heterocyclic compound, 3441-01-8, name is 3-Cyanobenzamide, molecular formula is C8H6N2O, 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. Quality Control of 3-Cyanobenzamide

General procedure: Amides (1 mmol) and Lawesson’s reagent (490 mg, 1.2 mmol) were added to dry THF (15 mL). The reaction mixture was stirred at room temperature for 1 h, or heated under reflux for 5 h in the case of the 4-nitro derivative. The solvent was evaporated under reduced pressure and the residue was partitioned between aq NaHCO3 (25 mL) and ethyl acetate (25 mL). The organic solvent was separated and dried over anhydrous MgSO4. The crude product was further purified by silica gel flash chromatography, using hexane-ethyl acetate (4:1), to yield the corresponding thioamides as yellow solids (42-60percent). 4-Nitrothioamide (2ff),38 4-cyanothiobenzamide (2gg)39 and 3-cyanothiobenzamide (2hh),40 3-methoxythiobenzamide (2ii)41 have been previously reported.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3441-01-8, its application will become more common.

Reference:
Article; Mayhoub, Abdelrahman S.; Marler, Laura; Kondratyuk, Tamara P.; Park, Eun-Jung; Pezzuto, John M.; Cushman, Mark; Bioorganic and Medicinal Chemistry; vol. 20; 1; (2012); p. 510 – 520;,
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Reference of 6609-56-9,Some common heterocyclic compound, 6609-56-9, name is 2-Methoxybenzonitrile, molecular formula is C8H7NO, 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 stirred solution of 2-methoxybenzonitrile (2.0 g, 15.0 mmol, 1 .83 mL) in ethanol (20 mL) were added hydroxylamine hydrochloride (2.09 g, 30.0 mmol), triethylamine (3.04 g, 30.0 mmol, 4.16 mL), and water (2 mL), then the mixture was heated to 70 00 for 1 5h. The mixture was cooled and quenched with water (20 mL), extracted with dichloromethane (30 mL x 3), and the combined organicphases were washed with water (20 mL), saturated aqueous sodium chloride solution (20 mL), dried overanhydrous sodium sulfate, filtered, and concentrated to give N-hydroxy-2-methoxybenzimidamide (2.80 g)as a light green solid, which was used in next step directly. 1H NMR (400 MHz, Methanol-d4) O 7.47 -7.30 (m, 2H), 7.06 (d, J8.4 Hz, 1H), 6.95 (t, J7.5 Hz, 1H), 3.86 (s, 3H).

The synthetic route of 6609-56-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 50397-74-5, name is 4-Amino-3-bromobenzonitrile, 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 50397-74-5, Product Details of 50397-74-5

General procedure: To provide nano-structures of (1), (2), and (3) by sonochemical method, a high-density ultrasonic probe immersed directly into the methanolic solution of Lx (25mL, 0.025M) in double distilled water, then into this solution, a proper volume of methanolic solution of AgNO3 (25mL, 0.025M) was added in a dropwise manner. The solution was ultrasonically irradiated with the power of 12 W for 1h. The obtained precipitates were filtered, subsequently washed with double distilled water and then dried at room temperature. The nanoparticles were characterized by powder X-ray diffraction (PXRD) and scanning electron microscopy (SEM).

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-3-bromobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zisti, Fatemeh; Tehrani, Alireza Azhdari; Alizadeh, Robabeh; Abbasi, Hamed; Morsali, Ali; Eichhorn, S. Holger; Journal of Solid State Chemistry; vol. 271; (2019); p. 29 – 39;,
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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. 1009-35-4, name is 4-Fluoro-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H3FN2O2

EXAMPLE 66(R)-trans-1-carbamoyl-4-adamantyl 3-(5-cyano-2-oxo-2,3-dihydro-1 H- benzo[d]imidazol-1 -yl)pyrrolidine-1 -carboxylateStep 1; A mixture of (R)-1-(methoxycarbonyl)adamantan-4-yl 3-aminopyrrolidine-1- carboxylate HCI salt (166 mg, 0.46 mmol), prepared as described in WO 2009/131669, 4-fluoro-3-nitrobenzonitrile (1 15 mg, 0.69 mmol), i-Pr2NEt (0.25 ml_, 1.4 mmol) and n-PrOH (3 ml.) was heated at 120 0C for 1 h in the microwave. The mixture was diluted with EtOAc (100 ml_), washed with water (10 ml_), 2percent aq HCI (10 ml.) and brine (10 ml_), and dried over Na2SO4. Removal of the solvent left an orange oil (293 mg) which was purified by prep HPLC to afford (R)-1- (methoxycarbonyl)adamantan-4-yl 3-((4-cyano-2-nitrophenyl)amino)pyrrolidine-1- carboxylate (80 mg, 37percent) as a yellow oil. LC-MS Method 1 tR = 1.93 min, m/z = 469.

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; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; LEFTHERIS, Katerina; SINGH, Suresh, B.; TICE, Colin, M.; YE, Yuanjie; ZHUANG, Linghang; WO2010/141424; (2010); 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 4513-77-3 as follows. COA of Formula: C7H9NO

2-Oxocyclohexane carbonitrile (5) (3.0 g, 0.024 mol), methyl-2-sulfanyl- acetate (6) (3.1 g, 0.029 mol) and p-toluenesulfonic acid (3.3 g, 0.024 mol) were dissolved in anhydrous acetic acid (100 mL) and the solution was stirred at room temperature for 40 h. The solvent was removed and the organic residue was dissolved in chloroform (150 mL) and then the mixture was washed with 2M NaOH (100 mL) and distilled water (3×50 mL). The organic phase was dried over MgSO4 and the solvent was evaporated. The product contained a mixture of two diastereoisomers (2:1). The pure major diastereoisomer was obtained after addition of Et2O (10 mL), subsequent sonification (5 min) and cooling down the solution in a freezer. The filtration of the precipitate offered a white solid, 3.00 g (63%). Mp 110-111 C; deltaH (CDCl3): 1.26 – 1.58 (2m, 2H, H7), 1.72 – 2.07 (2m, 4H, H8 and H9), 2.13 – 2.21 (m, 2H, H10), 3.03 – 3.07 (dd, J = 4.0, 10.7 Hz, 1H, H6), 3.74 (d, J = 16.8 Hz, 1H, one of H2), 4.04 (d, J = 16.8 Hz, 1H, one of H2); deltaC (CDCl3): 22.6 and 23.0 (2CH2 – C4 and C5), 27.9 (CH2 – C6), 32.4 (CH2 – C3), 39.5 (CH2 – C8), 42.2 (CH – C2), 91.0 (Ckv – C1), 118.5 (Ckv – C?N), 171.1 (Ckv – C10); IR (KBr): 935, 1016, 1061, 1117, 1196, 1227, 1255, 1350, 1404, 1446, 1618, 1782, 2243 (C?N), 2860, 2933, 2956, 2987; MS (EI, 70 eV): m/z (%) = 32 (80), 42 (40), 55 (55), 96 (30), 108 (10), 124 (100), 129 (35), 197 (M+, 35).

According to the analysis of related databases, 4513-77-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tenora, Luka?; Buchlovi?, Marian; Man, Stanislav; Pota?ek, Milan; Tetrahedron Letters; vol. 52; 3; (2011); p. 401 – 403;,
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Related Products of 114344-60-4, 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 114344-60-4 as follows.

3-Bromo-2-(1-((1s,3s)-3-methylcyclobutyl)-5-oxo-2,5-dihydro-1H-pyrrol-3-ylamino)benzonitrile4-Methoxy-1-((1s,3s)-3-methylcyclobutyl)-1H-pyrrol-2(5H)-one (4.20 g, 22.02 mmol) and 2-amino-3-bromobenzonitrile (5.94 g, 30.16 mmol) in acetic acid (15 mL) were warmed to 80 C. to give an amber solution. Methanesulfonic acid (3.57 mL, 55.04 mmol) in acetic acid (4 mL) was added drop wise into the reaction at 80 C. over one hour. After the addition, the reaction was stirred for another 30 minutes at 80 C. to complete. All of acetic acid was removed under high vacuum at 50 C. The residual was diluted in methylene chloride (150 mL) and then titrated into a half-saturated NaHCO3 aqueous solution at 0 C. slowly. The organic layer was dried through MgSO4, filtrated and evaporated to dry. The crude material was added to a silica gel column and was eluted with 0-10% methanol in methylene chloride to give an orange-yellow solid as the title compound (5.27 g, 68%) 1H NMR(300 MHz, CHLOROFORM-d) delta ppm 7.88 (dd, J=8.1, 1.4 Hz, 1 H) 7.67 (dd, J=7.7, 1.4 Hz, 1 H) 7.23 (t, J=8.01 Hz, 1 H) 6.02 (s, 1 H) 4.85 (s, 1 H) 4.39-4.63 (m, 1 H) 4.11 (s, 2 H) 2.29-2.50 (m, 2 H) 1.90-2.20 (m, 1 H) 1.59-1.79 (m, 2 H) 1.09 (d, J=6.5 Hz, 3 H). MS APCI, m/z=346.1/348.1 HPLC 2.19 min.

According to the analysis of related databases, 114344-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ASTRAZENECA AB; US2008/318943; (2008); A1;,
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Synthetic Route of 15996-76-6, The chemical industry reduces the impact on the environment during synthesis 15996-76-6, name is 4-(Aminomethyl)benzonitrile hydrochloride, I believe this compound will play a more active role in future production and life.

To a solution of 4-aminomethylbenzonitrile hydrochloride (n-1) (5.00 g, 29.7 mmol) in dichloromethane(167 mL), sodium carbonate (7.54 g, 71.2 mmol) was added. The reaction mixture was cooled to 0C and di-tert-butyl dicarbonate (7.57 mL, 32.6 mmol) was added; the resulting mixture was brought to room temperature at which it was stirred overnight. To the reaction mixture, water was added and extraction was conducted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvents were distilled off under reduced pressure and the residue was purified by silica gel (NH) column chromatography (n-hexane:ethyl acetate = 1:1) to give tert-butyl 4-cyanobenzylcarbamate (n-2) (amount, 6.48 g; yield, 94%).

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-(Aminomethyl)benzonitrile hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kaken Pharmaceutical Co Ltd; kegami, Satoru; Watanabe, Atsushi; Hirano, Kimio; Oyama, Tadashi; (62 pag.)KR2016/18745; (2016); A;,
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