Month: January 2021

Synthetic Route of 2042-37-7, 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 2042-37-7 as follows.

General procedure: The aryl halide (5.0 mmol), arylboronic acid (7.5 mmol), base (10.0 mmol), the calculated amount of thiourea, Pd and H2O (5 mL) were added to a flask containing a magnetic stir bar under air. The flask was sealed with a rubber septum and the contents were stirred at the specified temperature for the appropriate period of time. Upon completion, the reaction mixture was extracted using Et2O (3 10 mL). The solvent was removed on a rotary evaporator and the residue was purified by flash chromatography on silica gel to afford the desired product. The coupling products were characterized by 1H NMR and 13C NMR spectroscopy (see the Supporting Information). The identities of the products were confirmed by comparison with literature spectroscopic data.

According to the analysis of related databases, 2042-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chen, Wei; Lu, Xiao-Yan; Xu, Bei-Hua; Yu, Wei-Guo; Zhou, Zi-Niu; Hu, Ying; Synthesis; vol. 50; 7; (2018); p. 1499 – 1510;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 1591-37-3, 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. 1591-37-3, name is 2-Amino-6-methoxybenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 46 9-Amino-8-methoxy-4-oxa-1,2,3,4-tetrahydroacridine Following the method of Example 7, but substituting 2-amino-6-methoxybenzonitrile for anthranilonitrile afforded the title compound (11%, m.p. 205-207 C.). 1 H-NMR (CDCl3, 300 MHz,delta): 2H, m, 7.33 ppm; 1H, dd, 6.57 ppm (J=3, 6 Hz); 2H, bs, 5.92 ppm; 2H, t, 4.29 ppm (J=2, 6 Hz); 3H, s, 3.95 ppm; 2H, t, 2.5 ppm (J=2, 6 Hz); 2H, m, 2.13-2.07 ppm; TLC: (90:10:1-methylene chloride:methanol:28% aqueous ammonia) Rf -0.49.

The synthetic route of 2-Amino-6-methoxybenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US5202440; (1993); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 6136-93-2, 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. 6136-93-2, name is 2,2-Diethoxyacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE I Preparation of 2-Ethylidene-6-methyl-cis-3-heptenal A solution of 5.40 g of isobutylacetylene in 50 ml of diethyl ether is treated with 30 ml of 2.2 N n-butyllithium in hexane at -20 C, and after several minutes the resulting solution is treated with 8.50 g of diethoxyacetonitrile and then warmed slowly to room temperature. After about 1.5 hours the dark mixture is cooled and brought to a pH of about 2 with ten percent sulfuric acid. The layers are then separated and the organic layer is washed successively with water and saturated aqueous sodium bicarbonate solution and then dried over sodium sulfate. Evaporation of the solvent provides 4.6 g of a dark oil, shown by IR and NMR to contain 1,1-diethoxy-6-methyl-3-heptyn-2-one.

The synthetic route of 2,2-Diethoxyacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; International Flavors & Fragrances Inc.; US4024190; (1977); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts