Month: September 2021

Reference of 19924-43-7,Some common heterocyclic compound, 19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile, molecular formula is C9H9NO, 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: Amidoxime Formation To a solution of nitrile (1 eq.) in EtOH (12 mL mmol-1) was added hydroxylamine (50% v/v in H20, 4 mL mmol-1) and the reaction mixture heated under reflux for 5 hours. After removal of all volatiles under reduced pressure the crude produce was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Methoxyphenyl)acetonitrile, its application will become more common.

Reference:
Patent; IMPERIAL INNOVATIONS LIMITED; LEATHERBARROW, Robin; TATE, Edward; YU, Zhiyong; RACKHAM, Mark; WO2013/83991; (2013); A1;,
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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. 41963-20-6, name is 4-Bromo-3-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 4-Bromo-3-methylbenzonitrile

Preparations 27-31 are prepared essentially as described for Preparation 26 using the appropriate boronic acid and l-(3-bromo-pyridin-2-yl)-piperazine.Preparation 32: 3-Methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-benzonitrile Stir together 4-bromo-3-methylbenzonitrile (5.20 mmol, 1.02 g), bis(pinacolato) diboron (5.62 mmol, 1.43 g), potassium acetate (15.6 mmol, 1.53 g), and palladium acetate (0.16 mmol, 40 mg) in dry N,N-dimethylformamide (20 mL). Purge the reaction for 30 min. then heat to 85 0C overnight. Partition between water (100 mL) and ethyl acetate (100 mL), wash aqueous layer with ethyl acetate (100 mL). Combine ethyl –50-acetate washings and dry over magnesium sulfate, filter and concentrate in vacuo. Purify (silica gel chromatography, eluting with 0: 100 to 20:80 ethyl acetate:isohexane) to give the title preparation as a white powder (560 mg, 44% yield). MS (ES): m/z = 244 [M+H]+.

The synthetic route of 41963-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/141020; (2008); A1;,
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Reference of 876-31-3, 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. 876-31-3, name is 4-(Cyanomethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4-(1-Cyanocyclopentyl)benzonitrile [S11]. In a flamed dried 50 mL flask, 710.8 mg (5.0 mmol) of 2-(4-cyanophenyl)acetonitrile was dissolved in 7.5 mL anhydrous DMF. 316.0 mg (95% purity, 12.5 mmol, 2.5 equiv.) of NaH was added in portions at 0 C. and the reaction was allowed to stir for 1 hour at 0 C. 1.0797 g (0.59 mL, 5.0 mmol, 1.0 equiv.) of 1,4-dibromobutane was added dropwise at 0 C. and the reaction was allowed to stir overnight at room temperature. The reaction was quenched carefully with -10 mL water and extracted with 30 mL EtOAc three times. The combined organic layer was washed with 50 mL brine, dried with MgSO4, filtered, and concentrated. Flash column chromatography on silica (50 mm fritted glass column, 300 mL SiO2) using 5% EtOAc/hexanes?10% EtOAc/hexanes as eluent gave 880.1 mg (4.48 mmol) of pure product as a colorless oil (90% yield). 1H-NMR (500 MHz, CDCl3) delta 7.69-7.67 (m, 2H), 7.59-7.57 (m, 2H), 2.52-2.48 (m, 2H), 2.09-1.94 (m, 6H). 13C-NMR (126 MHz, CDCl3) delta 145.2, 132.8, 127.0, 123.3, 118.3, 112.0, 48.0, 40.7, 24.5. HRMS (EI+) m/z calculated for C13H12N2 [M]+: 196.1000, found 196.1004.

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

Reference:
Patent; The Board of Trustees of the University of Illinois; WHITE, M. Christina; ZHAO, Jinpeng; (94 pag.)US2020/87331; (2020); A1;,
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Adding a certain compound to certain chemical reactions, such as: 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, 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 654-70-6, Application In Synthesis of 4-Cyano-3-trifluoromethylaniline

[003 19j Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4C) of (R)-3-bromo-2-hydroxy-2-methylpropanoic acid (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 mm under the same condition. After 20mm, 5-amino-2-cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at RT. The solvent was removed under reduced pressure to give a solid which was treated with 300 mL of H20, extracted with EtOAc (2 x400 mL). The combined organic extracts were washed with saturated NaHCO3 solution (2 x 300 mL) and brine (300 mL). The organic layer was dried over MgSO4 and concentrated under reduced pressure togive a solid which was purified from column chromatography using CH2CWEtOAc (80:20) to give a solid. This solid was recrystallized from CH2CWhexane to give 55.8 g (73.9%) of (2R)-3-bromo- N-[4-cyano-3 -(trifluoromethyl)phenylj -2-hydroxy-2-methylpropanamide as a light-yellow solid. Mp 134.0-136.5C;[00320j ?H NMR (CDC13fFMS) oe 1.66 (s, 3H, CH3), 3.11 (s, 1H, OH), 3.63 (d, J= 10.8 Hz, 1H,CH2), 4.05 (d, J= 10.8 Hz, 1H, CH2), 7.85 (d, J= 8.4 Hz, 1H, Ar]), 7.99 (dd, J=2.1, 8.4 Hz, 1H,ArH), 8.12 (d, J = 2.1 Hz, 1H, ArH), 9.04 (bs, 1H, NH). MS (ESI) 349.0 [M – Hj M.p.: 124- 126C.

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

Reference:
Patent; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane D.; PONNUSAMY, Thamarai; HWANG, Dong-Jin; DUKE, Charles B.; COSS, Christopher C.; JONES, Amanda; DALTON, James T.; (159 pag.)WO2016/172330; (2016); A1;,
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Synthetic Route of 868-54-2,Some common heterocyclic compound, 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, molecular formula is C6H4N4, 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: Heterocyclic ketene aminals (1 mmol), aryl aldehydes (1.2 mmol), malononitriledimer (1.5 mmol), acetic acid (1 mmol), piperidine (1 mmol) and ethanol (10 mL)were stirred at refluxing for 1 h. After completion of the reaction (confirmed by TLC),the reaction mixture was filtered to afford the crude product, which was furtherwashed with 95% ethanol to give pure product 4.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, its application will become more common.

Reference:
Article; Sun, Feilong; Zhu, Fengjuan; Shao, Xusheng; Li, Zhong; Synlett; vol. 26; 16; (2015); p. 2306 – 2312;,
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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 21423-84-7 as follows. COA of Formula: C8H6ClN

To a solution of 2-chloro-4-methylbenzonitrile (1 .06 g, 7 mmol) and /V-bromosuccinimide (1 .37 g, 7.7 mmol) in acetonitrile (70 ml_) was added 2,2-azob/s(2-methylpropionitrile (0.230 g, 1 .4 mmol) under argon. The mixture was stirred at 80 C for 20 h. The reaction mixture was filtered and washed with ethyl acetate (80 ml_). The filtrate was concentrated, and the resulting crude material was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 10/1 ) to give 4-(bromomethyl)-2-chlorobenzonitrile as a light-yellow solid (0.661 g, 2.87 mmol, 41 %). 1 H NMR (400 MHz, Chloroform-d) d 7.67-7.69 (m, 1 H), 7.57-7.58 (m, 1 H), 7.41 (dd, J/ = 1 .5 Hz, J2= 8.0 Hz, 1 H), 4.454 (s, 2H).

According to the analysis of related databases, 21423-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YUMANITY THERAPEUTICS, INC.; LE BOURDONNEC, Bertrand; LUCAS, Matthew; OZBOYA, Kerem; PANDYA, Bhaumik; TARDIFF, Daniel; TIVITMAHAISOON, Parcharee; WRONA, Iwona; (475 pag.)WO2019/183587; (2019); A1;,
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Reference of 14447-18-8, The chemical industry reduces the impact on the environment during synthesis 14447-18-8, name is Benzyl cyanoacetate, I believe this compound will play a more active role in future production and life.

General procedure: A 100-mL round-bottom flask equipped with a stir bar is charged with dimethyl malonate (2.0 g, 15.0 mmol), crotonaldehyde (1.3 mL, 15.0 mmol), piperidine (0.2 mL, 3.0 mmol), benzoic acid (0.4 g, 3.0 mmol) and toluene (50 mL). The reaction mixture is heated at reflux using a Dean-Stark apparatus for 2 h. The toluene solution is washed with water, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by silica gel column chromatography eluting with hexanes/ethyl acetate (20/1) to afford 1a (1.7 g, 60% yield) as a red liquid.

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, Benzyl cyanoacetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Wei; Ghiviriga, Ion; Grenning, Alexander J.; Tetrahedron; vol. 73; 29; (2017); p. 4076 – 4083;,
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These common heterocyclic compound, 64113-85-5, name is 4-Methyl-[1,1′-biphenyl]-2-carbonitrile, 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. Product Details of 64113-85-5

General procedure: The heterocyclic derivative (0.99 mmol) and 5 mL THF is cooled to -78 oC, n-BuLi solution ( 0.5, mL, 1.2 eq) is added, the mixture is stirred 1 hr, after which 2-cyano-4-methyhlbiphenyl (192 mg, 0.99 mmol, dissolved in 5 mL THF) is added dropwise, The solution is then stirred 1 hr at -78 oC, then allowed to warm to room temperature and stirred for 6 hr. After this, 10 mL of 6M HCl is added and the mixture is stirred overnight. The solution is then basified with 10M NaOH and the products are partitioned between ether and water. The aqueous layer is further extracted (2x with ether) and the combined extracts are washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent is then removed under reduced pressure and the crude mixture is purified by column chromatography (1:1, hexanes: ethyl acetate).

The synthetic route of 4-Methyl-[1,1′-biphenyl]-2-carbonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Stentzel, Michael R.; Klumpp, Douglas A.; Tetrahedron Letters; vol. 60; 25; (2019); p. 1675 – 1677;,
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Electric Literature of 170230-29-2, A common heterocyclic compound, 170230-29-2, name is 4-Bromo-3-ethylbenzonitrile, molecular formula is C9H8BrN, 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.

Description 27; 2-ethyl-2′-fluoro-4-biphenylcarboxylic acid (D27); A mixture of 4-bromo-3-ethylbenzonitrile (D25) (651 mg, 3.10 mmol), 2- fluorophenylboronic acid (867 mg, 6.20 mmol), palladiumtetrakistriphenylphosphine (359 mg, 0.31 mmol) and potassium carbonate (1.29 g, 9.30 mmol) in dimethylformamide (10 ml.) was heated to 170 0C in the microwave for 30 minutes. The mixture was allowed to stand at room temperature over a weekend before it was poured into a mixture of ice and saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate (3 x 20 ml.) and the combined organics washed with brine, dried (phase separator) and evaporated. The residue was purified by silica chromatography, eluting 0-5 % EtOAc in hexane to give a colourless oil (655 mg). This material was added to ethanol (26 ml.) and water (6 ml.) followed by potassium hydroxide (1.62 g, 28.9 mmol) and the mixture heated to 90 0C for 17 h. The solvent was evaporated and the residue partitioned between ethyl acetate and 2M HCI. The organic layer was washed with further HCI before it was dried (phase separator) and concentrated in vacuo to give the title compound as a white solid (648 mg, 2.66 mmol). MS (ES”): Ci5H13FO2 requires 244; found 243 (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; GLAXO GROUP LIMITED; WO2008/74820; (2008); A1;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 1558-81-2, name is Ethyl 1-Cyano-1-cyclopropanecarboxylate, 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 1558-81-2, COA of Formula: C7H9NO2

To a mixture of ethyl 1-cyanocyclopropanecarboxylate (35.9mmol, 5g), dimethoxyethane (10OmL) and methanol (1OmL) was added sodium borohydride (287mmol, 10.87g) slowly and the mixture stirred at room temperature for 18 hours. The solution was diluted with saturated sodium hydrogen carbonate slowly and then extracted with 10% methanol / dichloromethane (x3). The organic layers were combined, dried over sodium sulphate and concentrated under vacuum to give the intermediate 1-(hydroxymethyl)cyclopropanecarbonitrile (2.36g). 1 H NMR (CDCI3, 400 MHz): delta 0.99 (2H, m), 1.28 (2H, m), 2.5 (1 H, br s), 3.62 (2H, s)

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, Ethyl 1-Cyano-1-cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; N.V. ORGANON; WO2009/24550; (2009); A1;,
Nitrile – Wikipedia,
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