Tag: M.W=100-200

50712-68-0, 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. 50712-68-0, name is 4-Chloro-2-methylbenzonitrile, A new synthetic method of this compound is introduced below.

2-(bromomethyl)-4-chlorobenzonitrileInto a 50-mL round-bottom flask, was placed a mixture of 4-chloro-2-methylbenzonitrile (1 g, 6.60 mmol, 1.00 equiv), CCl4 (15 mL), NBS (1.29 g, 7.25 mmol, 1.10 equiv) and BPO (50 mg, 0.20 mmol, 0.03 equiv). The resulted solution was stirred for 16 h at 80 C. The reaction mixture was cooled to 25 C. Then it was washed with 3¡Á15 mL of water. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by a silica gel column and eluted with ethyl acetate/ hexane (1:50). This resulted in 0.45 g (30%) of 2-(bromomethyl)-4-chlorobenzonitrile as a light yellow solid. LC-MS (ESI) m/z: Calculated for C8H5BrClN: 228.9. found: 230 [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; Global Blood Therapeutics, Inc.; Li, Zhe; Xu, Qing; Yu, Chul; Yee, Calvin; Gwaltney,, II, Stephen L.; Metcalf, Brian W.; Richards, Steven; Lardy, Matthew A.; Setti, Lina; Sham, Hing; US2015/315198; (2015); A1;,
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Some common heterocyclic compound, 453565-55-4, name is 5-Fluoroisophthalonitrile, molecular formula is C8H3FN2, 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. 453565-55-4

Example 15 To a solution of 1-(3-hydroxyphenyl)ethanol (69 mg) in 1-methyl-2-pyrrolidinone under a nitrogen atmosphere was added sodium hydride (60% in oil, 44 mg). The mixture was stirred at 20 C. for 10 minutes then 5-fluoroisophthalonitrile (0.161 g) was added and the mixture heated at 100 C. for 0.5 hour then at 150 C. for a further 0.5 hour. The cooled mixture was diluted (ethyl acetate), washed (water), dried over magnesium sulphate, evaporated and purified by dry column chromatography on silica (eluent dichloromethane/isohexane) to yield 1-(3,5-dicyanophenoxy)-3-[1-(3,5-dicyanophenoxy)ethyl]benzene (Compound 89, 84 mg), NMR (300 MHz, CDCl3) 7.56 (1H, t); 7.45-7.38 (2H, m); 7.32 (2H, d); 7.24 (2H, d); 7.22-7.18 (1H, m); 6.98 (1H, t); 6.92 (1H, dd); 5.29 (1H, quartet); 1.66 (3H, d).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 453565-55-4, its application will become more common.

Reference:
Patent; Cornell, Clive; Cramp, Michael Colin; Gingell, Michael; Westaway, Susan; US2003/181334; (2003); A1;,
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1558-82-3,Some common heterocyclic compound, 1558-82-3, name is Ethyl N-cyanoacetimidate, molecular formula is C5H8N2O, 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.

Intermediate 33Preparation of N’-cyano-N-(cyanomethyl)-N-methylacetimidamideTo a solution of ethyl N-cyanoacetimidate (1.12 g; 10 mmol) in ethanol (20 mL) was add 2-(methylamino)acetonitrile (0.736 g; 10.5 mmol) and the reaction mixture was stirred at room temperature for 24 h. The volatiles were removed under reduced pressure and the 1.36 g (100%) of the crude white solid were dried and used without further purification. ESI/APCI(+): 137 (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 Ethyl N-cyanoacetimidate, its application will become more common.

Reference:
Patent; KATHOLIEKE UNIVERSITEIT LEUVEN; US2012/316161; (2012); A1;,
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17626-40-3, name is 3,4-Diaminobenzonitrile, 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. 17626-40-3

A solution of 1 (557.5 mg, 2.5 mmol), 3, 4-diaminobenzonitrile (332.5 mg, 2.5 mmol), and benzoquinone (270.2 mg, 2.5 mmol) in ethanol (40 mL) was allowed to reflux under nitrogen for overnight. The reaction mixture was distilled off under reduced pressure. The residue was triturated with ether and filtered off to afford 2 in 90%, mp >340 C.’H NMR (DMSO-d6) ; J 7.20 (d, J = 8.4 Hz, 1 H), 7.68 (d, J = 8.4 Hz, 1 H), 7.86-7. 98 (m, 6H), 8.28 (s, 1 H), 8.57 (s, 1H), 12.80 (brs, 1H), 13.65 (brs, 1H). 13C NMR ; No. 158. 4, 153. 9,143. 5,132. 9, 131.0, 129.3, 126.7, 125.7, 119.7, 118.9, 118.1, 112.8, 109.4, 104.5. MS (m/z, rel. int. ); 336 (M+, 100), 307 (25), 280 (5), 164 (10). High resolution calcd. for C21H12N4O ms 336. 10111. Observed 336.10189. Anal. (C21H12N4O-0.25H2O) C, H, N.

Statistics shows that 17626-40-3 is playing an increasingly important role. we look forward to future research findings about 3,4-Diaminobenzonitrile.

Reference:
Patent; UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.; WO2005/40132; (2005); A1;,
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1080-74-6, name is 2-(3-Oxo-2,3-dihydro-1H-inden-1-ylidene)malononitrile, 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. 1080-74-6

General procedure: Compound 4 (400 mg, 0.47 mmol) and INCN (458 mg, 2.36 mmol) were dissolved in anhydrous chloroform (CF, 25 mL) and 0.3 mL of pyridine was slowly injected into mixture solution. Thereaction was stirred under a nitrogen atmosphere at 65 C for 12 h. Subsequently, the reaction vessel was cooled to room temperature and extracted with chloroform several times. The extracted organic layer were dried over MgSO4, filtered, and evaporated to obtain a residue. The mixture compound was then purified with column chromatography using chloroform to afford a dark solid.

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

Reference:
Article; Lee, Seong Lim; Kim, Hee Su; Ha, Jong-Woon; Park, Hea Jung; Hwang, Do-Hoon; Bulletin of the Korean Chemical Society; vol. 41; 2; (2020); p. 143 – 149;,
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403-54-3, Adding some certain compound to certain chemical reactions, such as: 403-54-3, name is 3-Fluorobenzonitrile, 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 403-54-3.

General procedure: To an oven-dried 15 mL sealed tube were added 2-aminophenylmethanol 1 (0.425 mmol), benzonitrile 2(0.25 mmol), Ru cat. b (1.94 mg, 1 mol%), and KOtBu (14.02 mg, 0.5equiv) intamyl alcohol (1 mL) under an air atmosphere. The sealedtube was capped and heated at 130C for 2 h. The reaction mixturewas cooled down to room temperature and directly concentratedunder vacuum. The crude mixture was puried by preparative thin-layer-chromatography (petroleum ether/ethyl acetate 20/1) togive the desired product 3 or 4.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 403-54-3.

Reference:
Article; Wan, Xiao-Min; Liu, Zi-Lin; Liu, Wan-Qing; Cao, Xiao-Niu; Zhu, Xinju; Zhao, Xue-Mei; Song, Bing; Hao, Xin-Qi; Liu, Guoji; Tetrahedron; vol. 75; 18; (2019); p. 2697 – 2705;,
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185147-08-4, The chemical industry reduces the impact on the environment during synthesis 185147-08-4, name is 4-Fluoro-3-methylbenzonitrile, I believe this compound will play a more active role in future production and life.

7.00 g (51.8 mmol) 4-fluoro-3-methyl-benzonitrile are heated to 110¡ã C. together with 1-N-methyl-[1,4]diazepan for 1 week with stirring. After evaporation i. vac. the residue is separated on aluminium oxide (eluant: dichloromethane) and the corresponding fractions are again purified on silica gel (eluting gradient: dichloromethane/methanol 100:1->9:1). Yield: 1.70 g (14percent) C14H19N3 (229.33) Mass spectrum: (M+H)+=230 Rf value: 0.25 (silica gel; dichloromethane/methanol=9:1)

The chemical industry reduces the impact on the environment during synthesis 4-Fluoro-3-methylbenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/203078; (2005); A1;,
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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.

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; 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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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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