Category: nitriles-buliding-blocks

5414-21-1, name is 5-Bromovaleronitrile, 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. Formula: C5H8BrN

In a four-neck reactor equipped with a thermometer, in a nitrogen stream, 2-hydrazinobenzothiazole 10.0 g (60.5 mmol) of DMF were dissolved in 100 ml of DMF . To this solution, 41.8 g (304 mmol) of potassium carbonate, And 10.34 g of 5-bromovaleronitrile ( 60.6 mmol), and the whole was stirred at 60 C. for 8 hours. After completion of the reaction, The reaction solution was added to 20 C., and the mixture was poured into 1,000 ml of water, And extracted with 1000 ml of ethyl acetate. After drying the ethyl acetate layer with anhydrous sodium sulfate, Sodium sulfate was filtered off. Ethyl acetate was distilled off from the filtrate under reduced pressure by a rotary evaporator, A yellow solid was obtained. This yellow solid was dissolved in Siri Kagel column chromatography (N-hexane: ethyl acetate = 60: 40) To obtain 6.82 g of Intermediate T as a white solid (yield: 45.7%).

The synthetic route of 5414-21-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZEON CORPORATION; SAKAMOTO, KEI; OKUYAMA, KUMI; SANUKI, KANAKO; (78 pag.)JP6090514; (2017); B1;,
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Synthetic Route of 90381-43-4,Some common heterocyclic compound, 90381-43-4, name is 7-Methoxy-2-naphthonitrile, molecular formula is C12H9NO, 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.

A solution of 7-methoxy-2-naphthonitrile (501 mg, 2.74 mmol) and KOH (503 mg, 9.0 mmol) in 95% ethanol (5 mL) is heated to reflux for 24 hours. The reaction mixture is allowed to cool, diluted with water and then acidified to pH<2 with concentrated HCl. The resulting precipitate is collected by filtration, washed with water and dried by heating at 70 C. under vacuum to give 7-methoxy-2-naphthoic acid as a white solid (540 mg, 98%). HRMS (FAB) calculated for C12H10O3+H+: 203.0708, found 203.0701. These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Methoxy-2-naphthonitrile, its application will become more common. Reference:
Patent; Jacobsen, Eric Jon; Myers, Jason K.; Walker, Daniel Patrick; Wishka, Donn G.; Reitz, Steven Charles; Piotrowski, David W.; Acker, Brad A.; Groppi JR., Vincent E.; US2003/236270; (2003); A1;,
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Synthetic Route of 915394-28-4, A common heterocyclic compound, 915394-28-4, name is 2-Methyl-2-(3-nitrophenyl)propanenitrile, molecular formula is C10H10N2O2, 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.

2-Methyl-2-(3-nitrophenyl)propanenitrile (0.6 g, 3.15 mmol) obtained in Step (1) above was stirred in a solvent of methanol. The reaction solution was mixed with Pd/C (0.06 g, 0.56 mmol), followed by stirring under hydrogen conditions for about 2 hours at room temperature. The reaction mixture was filtered through a Celite pad under reduced pressure, and washed with methanol. The filtrate was concentrated under reduced pressure to obtain the title compound (0.48 g, 95 %). 1H-NMR Spectrum (300 MHz, DMSO-d6): delta 7.06 (t, 1H), 6.71 (s, 1H), 6.61 (d, 1H), 6.52 (d, 1H), 5.21 (s, 2H), 1.61 (s, 6H). MS (ESI+, m/z): 161 [M+H]+

The synthetic route of 915394-28-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hanmi Pharm. Co., Ltd.; BAE, In Hwan; HAN, Sang Mi; KWAK, Eun Joo; AHN, Young Gil; SUH, Kwee Hyun; EP2876107; (2015); A1;,
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Synthetic Route of 654-70-6, A common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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.

4-Isothiocyanato-2-trifluoromethylbenzonitrile (96); 4-Amino-2-trifluoromethylbenzonitrile (2.23 g, 12 mmol) was added portionwise over 15 min into a well-stirred heterogeneous mixture of thiophosgene (1 mL, 13 mmol) in water (22 mL) at room temperature. Stirring was continued for an additional 1 h. The reaction medium was extracted with chloroform (3¡Á15 mL). The combined organic phase was dried over MgSO4 and evaporated to dryness under reduced pressure to yield desired product 4-Isothiocyanato-2-trifluoromethylbenzonitrile (96) (2.72 g, 11.9 mmol, 99%) as brownish solid and was used without further purification.

The synthetic route of 654-70-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of California; US2009/111864; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 67832-11-5, name is 4-Bromo-2-methylbenzonitrile, 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 67832-11-5, Recommanded Product: 67832-11-5

Methyl magnesium bromide (3 M in tetrahydrofuran) was added at rt drop wise to a solution of 4-bromo-2-methylbenzonitrile (4 g) in dry THF (15 mL) and was then heated to reflux for 2 h and then stirred at rt for 3 d. The mixture was chilled in an ice bath, saturated aqueous ammonium chloride solution (100 mL) was added and the mixture was extracted with EtOAc. The combined organic layers were concentrated under reduced pressure and the remaining residue was treated with 4 N HCl at 0 C. and was stirred at rt for 18 h. The mixture was extracted with EtOAc and the organic layer was washed with water, dried and the solvent was removed under reduced pressure to yield the desired product (88% yield).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194443; (2014); A1;,
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Application of 1187-42-4, These common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, 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.

The compound D (0.70 g, 1.50 mmol), diaminomaleonitrile (0.19 g, 1.80 mmol), 40 mL of ethanol, 40 mL of THF (tetrahydrofuran), and 0.23 mL of 12M hydrochloric acid were charged in a three-necked flask having a capacity of 300 mL, and then the resultant mixture was stirred while conducting heating at 40 C. for 24 hours. Water was added to the resultant solution, the resultant mixture was subjected to extraction with chloroform, and then the resultant extract was dried by adding sodium sulfate thereto. Sodium sulfate hydrate was removed by filtration, and the solvent was distilled off from the filtrate using an evaporator. The resulting solid was purified by silica gel column chromatography (developing solvent: toluene) to obtain a red solid (yield amount: 0.40 g, yield: 49%). Chemical shift values (delta) of the compound measured by 1H NMR (400 MHz, CDCl3) were as follows: delta 9.31 (d, J=8.8 Hz, 1H), 9.24 (dd, J=8.0 Hz, 1.2 Hz, 1H), 8.90 (d, 1.6 Hz, 1H), 8.78 (d, J=8.4 Hz, 1H), 8.13 (dd, J=8.4 Hz, 1.6 Hz, 1H), 8.05 (d, J=8.4 Hz, 2H), 8.00 (td, J=7.2 Hz, 1.6 Hz, 1H), 7.89 (td, J=7.2 Hz, 1.2 Hz 1H), 7.57 (d, J=8.4 Hz, 2H), 6.69 (m, 6H), 6.06 (dd, J=8.0 Hz 2.0 Hz, 2H). It was confirmed by 1H NMR measurement that the obtained compound was a compound 1 (Px-CNBQx).

The synthetic route of 1187-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KYUSHU UNIVERSITY, NATIONAL UNIVERSITY CORPORATION; Nippon Soda Co., Ltd.; YASUDA, Takuma; FURUE, Ryuhei; ISHIHARA, Hiroyuki; FUKUSHIMA, Yukio; (61 pag.)US2019/330162; (2019); A1;,
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Electric Literature of 17823-40-4, These common heterocyclic compound, 17823-40-4, name is 4-Bromo-2,3,5,6-tetrafluorobenzonitrile, 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.

A mixture of 4-cyanophenylboronic acid (1.83 g, 8 mmol), 4-bromo-2,3,5,6-tetrafluorobenzonitrile (1.0 g, 3.9 mmol), Pd2(dba)3 (0.18 g, 0.2 mmol), SPhos(0.16 g, 0.4 mmol) and K3PO4 (2.0 g, 8.7 mmol) in toluene (40 mL) was degassed and heated at about 120 C for about 16 hours. After cooled to room temperature, the mixture was filtered and washed with toluene. The filtrate was loaded on silica gel and purified by flash column using eluents of dichloromethane/hexane (10%to 40%). The desired fraction was collected and concentrated to give a white solid (Compound 10) (0.367 g, in 34% yield).

Statistics shows that 4-Bromo-2,3,5,6-tetrafluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 17823-40-4.

Reference:
Patent; NITTO DENKO CORPORATION; ZHENG, SHIJUN; BASIAGO, ADAM; (86 pag.)JP2016/526025; (2016); A;,
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Application of 630-18-2, 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. 630-18-2, name is Pivalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of nitrile (50 mmol), NaN3 (65 mmol), and Et3N¡¤HCl (150 mmol) in toluene (100 mL) was stirred at 110 C for 17-30 h (2b, 2f and 2l for 24 h; 2c and 2d for 17 h; 2e and 2j for 30 h). After cooling to r.t., the mixture was extracted with H2O (100 mL). To the aqueous layer, 36% HCl was added dropwise to acidic pH. After filtration, the solid was washed with water and dried under reduced pressure to give the expected tetrazole 2. The corresponding physical and spectroscopic data for tetrazoles 2 are detailed below.

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, Pivalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Behloul, Cherif; Bouchelouche, Kenza; Hadji, Yasmine; Benseghir, Saadia; Guijarro, David; Najera, Carmen; Yus, Miguel; Synthesis; vol. 48; 15; (2016); p. 2455 – 2460;,
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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. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Product Details of 179897-89-3

(1) 5-bromo-2-fluoro-1-cyanobenzene (II, 3 g, 15 mmol) under N2 protection,Sodium sulfide (1.3 g, 16.5 mmol) was reacted in DMF (30 mL) at room temperature for 5 h.Add 300 mL of sodium hydroxide solution (1 mol/L) and stir for 0.5 h.Wash with dichloromethane (300 mL ¡Á 2), acid phase with hydrochloric acid (6 mol / L) to pH = 2, dichloromethane (400 mL ¡Á 2),The combined organic layers were washed with brine, dried over anhydrous magnesium5-bromo-2-thio-1-cyanobenzene (III)1.0 g, yield 31.2%.

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; South China University of Technology; Li Jing; Li Xiaolei; Zhou Haiyan; Wu Fangping; Zhang Lei; (12 pag.)CN108218777; (2018); A;,
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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 4640-66-8 as follows. Product Details of 4640-66-8

General procedure: To a 0.5-2.0ml vial with 1 mmol ketone (1 eq) issolved in 2-pentanol (1.66 M) was added 1.1 eq of aromatic aldehyde and catalytic piperidine (0.08 eq), stirring vigorously. After heating under muWave for 15min at 120 C, the reaction was cooled to r.t. and precipitate was vacuum filtered and washed with minimal, cold hexanes. After drying under vacuum, solid was analyzed via NMR, IR, and mp.

According to the analysis of related databases, 4640-66-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Deshpande, Shyam J.; Leger, Paul R.; Sieck, Stephen R.; Tetrahedron Letters; vol. 53; 14; (2012); p. 1772 – 1775;,
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