Category: nitriles-buliding-blocks

Application of 6621-59-6,Some common heterocyclic compound, 6621-59-6, name is 6-Bromohexanenitrile, molecular formula is C6H10BrN, 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 4Preparation of (R)-4-trimethylammonio-3-[3-[6-(2-phenylethoxy)hex-l- yl]ureido]butyrate Inner SaltPreparation of the intermediate -^-phenylethoxylhexanitrile[0077] Sodium hydride (60% in oil, 1.38 g, 34.38 mmol) was suspended in N,N- dimethylformamide (45 mL) with ice cooling under N2. 2-Phenylethanol (3.43 mL, 28.65 mmol) was added over approx. 5 minutes. After stirring for a further 30 minutes, 6- bromohexanenitrile (4.56 mL, 34.38 mmol) was introduced dropwise. Following complete addition, the mixture was allowed to come to room temperature and was stirred for 19h. Thereafter it was heated to 500C for 3h, then at room temperature for an additional 18h. Water (200 mL) and ethyl acetate (200 mL) were added. The phases were separated and the aqueous phase extracted further with ethyl acetate (2 x 100 mL). The combined organic phases were dried (MgSO4), filtered and evaporated to give a pale, yellow free flowing oil. Chromatography over SiO2 (isohexane-20% ethyl acetate/isohexane gradient) gave the title compound as a colorless oil (1.55 g, 25%). LCMS: Rt = 3.01 min, m/z = 217.92, 154.67, 145.79. 1H NMR (400 MHz, CDCl3): 7.24-7.1 1 (m, 5H), 3.55 (t, J= 7.07 Hz, 2H), 3.37 (t, J = 6.32 Hz, 2H), 3.35 (t, J= 6.57 Hz, 2H), 2.80 (t, J= 7.07 Hz, 2H), 2.23-2.20 (m, 3H), 1.62- 1.40 (m, 10H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromohexanenitrile, its application will become more common.

Reference:
Patent; DARA BIOSCIENCES, INC.; MIDDLEMISS, David; INGOLD, Kenneth, J.; WO2010/8473; (2010); 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. 630-18-2, name is Pivalonitrile, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

General procedure: To a solution of 4-bromobiphenyl 1a (3.0 mmol, 699.3 mg) in THF (3.0 mL) was added n-BuLi (4.5 mmol, 1.55 M in hexane, 2.87 mL) at 50 C. The obtained mixture was stirred for 30 min at 50 C under an argon atmosphere. Pivalonitrile (6.0 mmol, 498.8 mg) in THF (2.0 mL) was added to the mixture at 50 C and the obtained mixture was stirred for 30 min in the temperature range of 50 C to room temperature. MeOH (2.0 mL) was added to the mixture. Then, I2 (12.0 mmol, 3045.6 mg) and K2CO3 (12.0 mmol, 1658.4 mg) were added to the mixture at room temperature, and the obtained mixture was stirred for 6 h at 70 C. Sat. aq. Na2SO3 solution (20.0 mL) was added to the reaction mixture, and the product was extracted with AcOEt (10.0 mL x 3). The organic layer was dried over Na2SO4. After filtration and removal of the solvent, the residue was purified by silica-gel column chromatography (chloroform: n-hexane 1:1) to give 4-cyanobiphenyl 2a (451.6 mg, 84%).

The synthetic route of 630-18-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Uchida, Ko; Togo, Hideo; Tetrahedron; vol. 75; 39; (2019);,
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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. 149793-69-1, name is 3-Fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 149793-69-1

A mixture of [3-FLUORO-5- (TRIFLUOROMETHYL)-BENZONITRILE (LANCASTER] Synthesis GmbH; 17 g, 89 [MMOL)] and 2-methylimidazole (Fluka, Buchs, Switzerland ; 22.2 g, 270 [MMOL)] in N, N- dimethylacetamide (80 mL) is stirred at [145C] for 19 h. The solvent is evaporated off under reduced pressure and the residue is dissolved in ethyl acetate (200 mL). The solution is washed with brine (200 mL), dried [(NA2SO4)] and the solvent is evaporated off under reduced pressure to give the crude product which is purified by recrystallisation from ether-hexane to afford the title compound as yellow crystalline solid, m. p. [132-134C.]

The synthetic route of 149793-69-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2004/5281; (2004); A1;,
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Some common heterocyclic compound, 3672-47-7, name is 3-(4-Methoxyphenyl)-3-oxopropanenitrile, molecular formula is C10H9NO2, 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. Application In Synthesis of 3-(4-Methoxyphenyl)-3-oxopropanenitrile

General procedure: Benzoyl acetonitrile (1, 0.5 mmol), cyclic 2-diazo-1,3-dicarbonyl compound (2, 1.25 mmol), [RhCp*Cl2]2 (0.025 mmol), CsOAc (0.25 mmol), Cu(OAc)2*H2O (1.0 mmol) and DCE (2 mL) were sequentially charged into a reaction tube. The tube was then sealed and the mixture was stirred at 80 C. Upon completion, it was cooled to room temperature, quenched with saturated brine (10 mL), and extracted with EtOAc (10 mL * 3). The combined organic phase was dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether/ethyl acetate (5:1) as eluent to afford 3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3672-47-7, its application will become more common.

Reference:
Article; Zhang, Beibei; Li, Bin; Guo, Chenhao; Zhang, Xinying; Fan, Xuesen; Tetrahedron Letters; vol. 59; 32; (2018); p. 3094 – 3099;,
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Application of 60710-80-7, A common heterocyclic compound, 60710-80-7, name is 3-Amino-4-methylbenzonitrile, molecular formula is C8H8N2, 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.

To a suspension of imidazo[1 ,2-a]pyridine-3-carboxylic acid (1 ) (16.6 g, 102 mmol) in dichloromethane (300 mL) and DMF (0.5 mL) at 0 C was added oxalyl chloride (45 mL, 510 mmol) dropwise over 10 minutes. The reaction was slowly warmed to room temperature and stirred until complete conversion was detected by LCMS in MeOH. The reaction was subsequently reduced to dryness and suspended in dichloroethane (100 mL) and was added to a solution of 3-amino-4-methylbenzonitrile (7) (15 g, 1 13 mmol) in dichloroethane (200 ml_) and Pr2NEt (55 ml_) at 0 C. After the addition, the cold bath was removed and contents were stirred at room temperature for 1 hour and then heated to 50 C for another 2 hours. After the completion of the reaction, the mixture was cooled and a white precipitate formed. The mixture was filtered and the solid was washed with cold dichloromethane. About 10 g of the desired N-(5-cyano-2- methylphenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (8) was obtained. The filtrate was washed with saturated NH4CI, saturated NaHC03, brine, dried over magnesium sulfate, filtered and reduced to dryness. The crude solid was triturated with diethyl ether to remove excess aniline and filtered to afford another crop of N-(5-cyano-2- methylphenyl)imidazo[1 ,2-a]pyridine-3-carboxamide (8) as a white solid. MS m/z 277.1 (M+1 ).

The synthetic route of 60710-80-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IRM LLC; LOREN, Jon; LI, Xiaolin; LIU, Xiaodong; MOLTENI, Valentina; NABAKKA, Juliet; NGUYEN, Bao; PETRASSI, Hank Michael James; YEH, Vince; RUCKER, Paul Vincent; WO2013/33203; (2013); A1;,
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Reference of 63968-85-4,Some common heterocyclic compound, 63968-85-4, name is 2-(Trifluoromethoxy)benzonitrile, molecular formula is C8H4F3NO, 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 mixture of2-(trifluoromethoxy)benzonitrile (0.342 mL, 1.999 mmol) and sodium borodeuteride (192mg, 4.60 mmol) in THF (10 mL) at 0 C was added over 45 mm, iodine (507 mg, 1.999mmol) as a solution in THF (4 ml). The reaction mixture was refluxed for 2 h. At thistime, it was cooled to 0 C and 6 N HC1 (2 ml) was carefully added. This mixture wasrefluxed for 30 mm. After cooling to rt, the mixture was partitioned between EtOAc (40ml) and iN NaOH (40 ml). The organic layer was washed with water (20 ml) and brine(20 ml). After drying (Na2504) and filtration, the organic layer was concentrated toafford 2-(trifluoromethoxy)dideuterobenzylammne (385 mg, 1.993 mmol, 100 % yield) asa light yellow oil. The material was impure and was used crude in the coupling step.

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

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; GUO, Junqing; HART, Amy, C.; MACOR, John, E.; MERTZMAN, Michael, E.; PITTS, William, J.; SPERGEL, Steven, H.; WATTERSON, Scott, Hunter; ANDAPPAN MURUGAIAH SUBBAIAH, Murugaiah; CHEN, Jie; DZIERBA, Carolyn, Diane; LUO, Guanglin; SHI, Jianliang; SIT, Sing-Yuen; (428 pag.)WO2018/148626; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 868-54-2, name is 2-Aminoprop-1-ene-1,1,3-tricarbonitrile, 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 868-54-2, name: 2-Aminoprop-1-ene-1,1,3-tricarbonitrile

General procedure: Et3N (0.3 mmol) was added to a stirred solution of salicylaldehyde (3 mmol), 2-aminoprop-1-ene-1,1,3-tricarbonitrile (3 mmol) and 3-trifluoromethyl-2-pyrazolin-5-one in 5 ml of n-PrOH at ambient temperature. Then mixture was refluxed for 4 h. After the reaction was finished and cooled the solid was filtered and dried to isolate pure substituted 2,4-diamino-5-(5-hydroxy-3-(trifluoromethyl)-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile. In some cases cristallisation from EtOH-DMSO is needed.

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:
Article; Elinson, Michail N.; Vereshchagin, Anatoly N.; Anisina, Yuliya E.; Fakhrutdinov, Artem N.; Goloveshkin, Alexander S.; Egorov, Mikhail P.; Journal of Fluorine Chemistry; vol. 213; (2018); p. 31 – 36;,
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Reference of 59997-51-2, 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. 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step j03:[0668]At room temperature 4,4-dimethyl-3-oxopentanenitrile (J-II) (1 equivalents, 5 g) was taken up in ethanol (100 mL), mixed with hydrazine hydrate (2 equivalents, 4.42 g) and refluxed for 3 h. The residue obtained after removal of the ethanol by distillation was taken up in water (100 mL) and extracted with ethyl acetate (300 mL). The combined organic phases were dried over sodium sulfate, the solvent was removed under vacuum and the product (JAI) (5 g, 89% yield) was obtained as a light red solid after recrystallisation from n-hexane (200 mL).

The synthetic route of 4,4-Dimethyl-3-oxopentanenitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; US2013/29962; (2013); A1;,
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Reference of 2338-75-2,Some common heterocyclic compound, 2338-75-2, name is 4-(Trifluoromethyl)phenylacetonitrile, molecular formula is C9H6F3N, 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 50 mL of anhydrous ethnol was added NaOH (160 mg,4 mmol), 2-formyl pyrrole (380.4 mg, 4 mmol) and 4-trifluoromethyl benzyl cyanide (624 muL, 4 mmol). The reaction was heated to reflux with stirring for 3 h. After cooled to room temperature, the reaction solution was evaporated in vacuum. The residue was purified by silica gel column (hexane:ethyl actate = 40: 1) to give 10b as yellow solid ( 596 mg, 56.9%). 1H NMR (400MHz, CDCl3), delta 9.82 (s, 1H), 7.70-7.65 (m, 4H), 7.48 (s, 1H), 7.12-7.11 (dd, J = 4.0, 2.7Hz, 1H), 6.77-6.76 (m, 1H), 6.40-6.37 (dt, J = 3.7, 2.5 Hz, 1H).

The synthetic route of 2338-75-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Ji-An; Zhang, Zhen-Yu; Gao, Jie; Tan, Jia-Hui; Gu, Xian-Feng; Tetrahedron Letters; (2019);,
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Synthetic Route of 796600-15-2, A common heterocyclic compound, 796600-15-2, name is 2-Chloro-4-fluoro-3-methylbenzonitrile, molecular formula is C8H5ClFN, 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.

Examples 11 and 12Example 11 Example 12 11a to l ib(R)-2-(3 -chloro-4-cyano-2-methylphenylamino)-3 -hydroxypropanoic acidTo a stirred solution of 2-chloro-4-fluoro-3-methylbenzonitrile (1 la) (1.0 gm, 5.8 mmol) in DMSO (10 mL), D-Serine (1.4 gm, 13.3 mmol) was added followed by K2C03 (1.7 gm, 12.3 mmol) at room temperature. The resulting reaction mixture was heated to 90C for 12 h. After completion of reaction (by TLC), the reaction mixture was poured into ice-cold water (300 mL) and extracted with EtOAc (100 mL). The aqueous layer was acidified with citric acid (pH ~3) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over Na2S04, and concentrated under reduced pressure to afford the acid 1 lb (0.3 gm, crude) as off- white solid. The crude material was taken for the next step without purification.TLC: 10% MeOH/DCM (Rf: 0.2)1H NMR (500MHz, DMSO-c?, delta in ppm): 8.2-10.2 (br s, 1H), 7.54 (d, J= 8.5 Hz, 1H), 6.57 (d, J= 9.0 Hz, 1H), 5.79 (d, J= 7.5 Hz, 1H), 4.20 (t, J= 3.0 Hz, 1H), 3.86-3.79 (m, 2H), 3.22 (br s, 1H), 2.25 (s, 3H).

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; RADIUS HEALTH, INC.; MILLER, Chris, P.; WO2012/47617; (2012); A1;,
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