Category: nitriles-buliding-blocks

3939-09-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 3939-09-1, name is 2,4-Difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

1-(2-Cyano-5-fluoro-phenyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester. To a solution of methyl 1H-1,2,4-triazole-3-carboxylate (27 g, 215 mmol) in dimethylformamide (170 mL) was added sodium hydride (5.53 g, 95%, 217 mmol) and the mixture was stirred for 30 min. Added to this was 2,4-difluorobenzylnitrile (30 g, 217 mmol) and the resulting mixture stirred at room temp for 60 h. The mixture was diluted with water and filtered to remove solids. The solution was extracted with ethyl acetate and the organic phase was washed with water (3¡Á’s) and brine, then dried (Na2SO4) and concentrated. The resulting residue was purified by flash chromatography (SiO2) eluting with 30% tetrahydrofuran/20% CH2Cl2/50% hexane to give the title compound as white needles (5.34 g, 10% yield). 1H-NMR (300 MHz, CDCl3) delta ppm: 8.92 (1H, s), 7.85 (1H, dd, J=8.8, 5.5 Hz), 7.67 (1H, dd, J=8.8, 2.6 Hz), 7.34-7.27 (1H, m), 40.3 (3H, s). LCMS [M+H]+ calcd for C11H8N4FO2: 247.06. found: 247.11.

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Reference:
Patent; Bristol-Myers Squibb Company; US2007/129379; (2007); A1;,
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622-75-3, A common compound: 622-75-3, name is 2,2′-(1,4-Phenylene)diacetonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Weigh 1,4-benzenediacetonitrile 0.807 g (5.17 mmoL) was dissolved in 20 mL of ethanol,Add NaOH for 0.5h, weighed the first step of the synthesis of the product 3g (10.3mmoL) added to the flask for 3h,The reaction solution was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was distilled off under reduced pressure,To give 2.75 g of a pale yellow solid;

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, 2,2′-(1,4-Phenylene)diacetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hefei University of Technology; LU, HONG BO; ZHANG, SHAN NA; YANG, JIA XIANG; LU, GUO QIANG; QIU, LONG ZHEN; ZHANG, GUI YU; XU, WEI; (11 pag.)CN103641742; (2016); B;,
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1953-99-7, A common compound: 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, belongs to nitriles-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

In a 100 ml flask, 3,4,5,6-tetrachlorophthalonitrile (5 g), 2-phenylphenol (3.201 g), K2CO3 (3.898 g)And acetonitrile (50 ml), and reflux while heating. After completion of the reaction, the mixture was filtered, washed with tetrahydrofuran (THF)The resulting solid was dissolved in a small amount of dichloromethane and then hexane was added thereto to obtain a solid (4- (biphenyl-2-ylamino) -3,5,6-trichlorophthalonitrile). At this time, the obtained solid was washed several times, filtered and vacuum dried.

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, 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Cheil Industries Co., Ltd.; Choe, Say Young; Kwon, JaeYoung; Park, Uhn B; Lee, Jong Son; Lee, Chang Ryul; Jong, Ju Ho; Choe, Mi Jin; Choe, Sung Gip; Hyung, Gyung Hee; (28 pag.)KR2015/130131; (2015); A;,
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4640-67-9, Name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, 4640-67-9, 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.

According to the method described in Embodiment 1,Add 1f (0.5 mmol, 82 mg), 2a (1.25 mmol, 173 mg) to a 15 mL pressure tube. Dichloro(pentamethylcyclopentadienyl)rhodium(III)dimer (0.025 mmol, 15 mg), copper acetate monohydrate (1 mmol, 200 mg), cesium acetate (0.25 mmol, 48 mg) and 1,2-Dichloroethane (2 mL) was sealed under an air atmosphere, and then placed in an oil bath at 80 C for 14 h. The reaction was quenched with 10mL of water was added, extracted with ethyl acetate (10mL ¡Á 3),The organic phase was washed successively with water and saturated brine and dried over anhydrous sodium sulfate. Filtration, rotary evaporation, over silica gel (petroleum ether/ethyl acetate = 5/1) to give a yellow solid column 3fa (141mg, 81%).

Statistics shows that 3-(4-Fluorophenyl)-3-oxopropanenitrile is playing an increasingly important role. we look forward to future research findings about 4640-67-9.

Reference:
Patent; Henan Normal University; Fan Xuesen; Guo Chenhao; Zhang Beibei; Zhang Xinying; Li Bin; (17 pag.)CN108997298; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, 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 6011-14-9, 6011-14-9

A solution of 4-(2-((6-carboxy-2-(3,4-dichloro-5-methyl-1H-pyrrole-2-carboxamido)benzo[d]thiazol-4- yl)oxy)ethyl)morpholin-4-ium chloride (Example 10) (19 mg, 0.035 mmol) in N,N-dimethylformamide (4 mL) was cooled to 0 C and then EDC (8 mg, 0.042 mmol), HOBt (6 mg, 0.046 mmol) and N- methylmorpholine (12 muL, 0.106 mmol) were added and the reaction mixture stirred for 20 min at 0 C. Then aminoacetonitrile hydrochloride (5 mg, 0.053 mmol) was added and reaction mixture stirred overnight at room temperature. The solvent was evaporated in vacuo, to the residue ethyl acetate (10 mL) and 1M HCl (10 mL) were added after which the precipitate formed. The solid was filtered off and dried. Yield: 14 mg (68.0%); beige solid. (0686) 1H NMR (400 MHz, DMSO-d6) d 2.29 (s, 3H), 3.25-3.34 (m, 2H), 3.62-3.73 (m, 4H), 3.76-3.88 (m, 2H), 4.01-4.10 (m, 2H), 4.36 (d, J = 5.4 Hz, 2H), 4.71 (t, 2H), 7.62 (d, J = 1.5 Hz, 1H), 8.21 (d, J = 0.5 Hz, 1H), 9.40 (t, J = 5.5 Hz, 1H), 10.93 (s, 1H), 12.20 (s, 1H), 12.78 (s, 1H). (0687) HRMS (ESI+) m/z for C22H23Cl2N6O4S ([M+H]+): calculated 537.0873, found 537.0861.HPLC: tr 4.313 min (96.9 % at 254 nm, 97.7 % at 280 nm), method A

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, 2-Aminoacetonitrile hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERZA V LJUBLJANI; MTA SZEGEDI BIOLOGIAI KUTATOKOeZPONT; HELSINGIN YLIOPISTO; TOMA?IC, Tihomir; ZIDAR, Nace; DURCIK, Martina; ILA?, Janez; ZEGA, Anamarija; DURANTE CRUZ, Cristina; TAMMELA, Paeivi; PAL, Csaba; NYERGES, Akos Jozsef; KIKELJ, Danijel; MA?IC, Lucija Peterlin; (116 pag.)WO2020/48949; (2020); A1;,
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2973-50-4, 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 2973-50-4 as follows.

General procedure: N,N’-di(2-fluorophenyl)-4-methoxyl-isophthalamide(1a): Equipped a stirrer in a three-necked flask (100 ml), to a mixture of 2-fluoroaniline (1.11 g, 10.0 mmol),anhydrous tetrahydrofuran (15 ml) and dry pyridine (1 ml), dropwise added 4-methoxyl-isophthaloyl dichloride (1.17 g, 5.0 mmol) which had been dissolved in dry tetrahydrofuran (10 ml). After the mixture reaction at room temperature for 8 h under continuous stirring, the excess tetrahydrofuran was distilled off in vacuum. The residue was recrystallized by acetone. Its melting point is 204-206 C, and yield is 67%. The other compounds 1b-1j, 2a-2k, 3a-3l and 4a-4h were prepared in the same manner.

According to the analysis of related databases, 2-(2-Aminophenyl)acetonitrile, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Xiu Jie; Shi, Xin Xin; Zhong, Yong Liang; Liu, Ning; Liu, Kai; Bioorganic and medicinal chemistry letters; vol. 22; 21; (2012); p. 6591 – 6595,5;,
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Adding a certain compound to certain chemical reactions, such as: 6136-68-1, name is 3-Acetylbenzonitrile, 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 6136-68-1, 6136-68-1

6M Sodium hydroxide (25 mL) was added to 3-acetylbenzonitrile (850 mg, 5.82 mmol) in methanol (25 mL) and then heated at [90C] overnight. After concentrating the reaction mixture, the aqueous layer was washed with dichloromethane (2x), then acidified [PH-3] with 12M HC1. The precipitate was extracted with ethyl acetate then washed with water and saturated brine, dried over anhydrous sodium sulfate filtered and concentrated to afford 3-ethylbenzoic acid as a colorless oil; 0.800g (92%). 1H NMR [(CDC13)] 8 [(PPM)] : 8.70 (s, 2H), 8.33 (d, 2H), 8. 24 (d, 2H), 7.64 (t, 1H), 2.70 (s, 3H).

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

Reference:
Patent; ASTRA ZENECA AB; NPS PHARMACEUTICALS, INC.; WO2004/14881; (2004); A2;,
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A common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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. 16588-02-6.

General procedure: To solution of 1.97 mmol (1.2 eq.) of phenol 2-8, 12-13 in 3 ml dry DMSO was added 79 mg(1.2 eq.) powdered NaOH. The mixture was heated at 50C for 20 min and to the formed clearsolution 0.300 g (1.64 mmol, 1.0 eq.) of 1 was added. The reaction mixture was heated at 80C for 8h. After cooling 40 ml water was added and extracted with DCM. The organic phase was washedwith aq. NaHCO3 and water, dried over Na2SO4, filtered and evaporated in vacuo. The crudeproducts 14-20, 24-25 were purified by column chromatography (50 g silica-gel). After column theformed solid products were powdered, washed with 3 ml hot hexane and dried in vacuo.

The synthetic route of 2-Chloro-5-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Dobrikov, Georgi M.; Slavchev, Ivaylo; Nikolova, Ivanka; Stoyanova, Adelina; Nikolova, Nadya; Mukova, Lucia; Nikolova, Rosica; Shivachev, Boris; Galabov, Angel S.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 19; (2017); p. 4540 – 4543;,
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1080-74-6, Name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 1080-74-6, 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.

As shown in the above reaction formula,The formula (2-8-a-3) obtained in the above Preparation Example 1The compound shown (129 mg, 0.1 mmol),a compound of the formula (a-2-1) (92 mg, 0.4 mmol),Pyridine (0.8 mL, 0.96 mmol) and chloroform(30 mL) was added to the reaction vessel,Argon gas for 25 minutes,It was then refluxed at 65 C for 12 h.After cooling to room temperature (about 25 C),The reaction product was poured into 200 mL of methanol and filtered.The obtained precipitate was sieved on a silica gel column (using 200-300 mesh silica gel,The eluent is a petroleum ether/dichloromethane in a volume ratio of 1:2 for chromatographic separation.Obtained a blue solid (147 mg, yield: 89.1%).That is, the poly-fused ring conjugated macromolecule represented by the formula (1-8-a-3).

Statistics shows that 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile is playing an increasingly important role. we look forward to future research findings about 1080-74-6.

Reference:
Patent; Peking University; Zhan Xiaowei; Zhu Jingshuai; Lin Yuze; (40 pag.)CN109651393; (2019); A;,
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6136-68-1,Some common heterocyclic compound, 6136-68-1, name is 3-Acetylbenzonitrile, molecular formula is C9H7NO, 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 34A Ethyl 4-(3-cyanophenyl)-1,3-thiazole-2-carboxylate At room temperature, 10 drops of a conc. aqueous hydrogen chloride solution are added to 5.00 g (34.4 mmol) of 3-acetylbenzenecarbonitrile in 40 ml of conc. acetic acid. 1.8 ml (34.4 mmol) of bromine in 10 ml of conc. acetic acid are subsequently added dropwise over a period of 1 h, and after the end of the addition, the reaction mixture is poured onto ice. After extraction of the aqueous phase with dichloromethane, the combined organic phases are dried over MgSO4, filtered and concentrated under reduced pressure. The solid obtained (8.00 g) is provided in 250 ml of EtOH and heated under reflux, a solution of 3.77 g (28.3 mmol) of ethyl amino(thioxo)acetate in 50 ml of ethanol is added dropwise and the mixture is stirred under reflux for 3 h. The reaction solution is cooled and the precipitate formed is collected by filtration. The mother liquor is concentrated under reduced pressure, the residue is taken up in a little ethanol and the solid formed is subsequently collected by filtration. 5.75 g (65% of theory) of the title compound are obtained after combining the solids. 1H-NMR (400 MHz, DMSO-d6): delta=8.74 (s, 1H), 8.45 (s, 1H), 8.35 (d, 1H), 7.88 (d, 1H), 7.77-7.62 (m, 1H), 4.43 (q, 2H), 1.37 (t, 3H). LC-MS (Method 5): Rt=1.15 min; MS (ESIpos): m/z=259 [M+H]+.

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

Reference:
Patent; AiCuris GmbH & Co. KG; Thede, Kai; Greschat, Susanne; Gericke, Kersten Matthias; Wildum, Steffen; Paulsen, Daniela; US2013/45999; (2013); A1;,
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