Tag: M.W=100-200

Electric Literature of 939-79-7,Some common heterocyclic compound, 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, molecular formula is C8H6N2O2, 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: The reaction materials were 2-nitro-4-cyanotoluene (162 mg, 1 mmol), butyl methacrylate (430 mg, 3 mmol) for 8 hours, and the specific operation was the same as in Example 1. The product was a white solid, yield 158 mg, yield 58%.;_A 10 mL round bottom flask equipped with a reflux condenser was charged with 2,4-dinitrotoluene (182 mg, 1 mmol). methyl methacrylate (294 mg, 3 mmol) and cesium carbonate (652 mg, 2 mmol). Nitrogen was bubbled through anhydrous THF (5 mL), heated to 65 C and refluxed for 12 hours. After the end of the reaction, the solvent is removed by rotary evaporation and the excess olefin is removed. The residual solid is washed with sufficient amount of methylene chloride, filtered, the residue is dissolved in sufficient water. After removal of the solid, the solvent was dried and dried in vacuo to give recovered cesium carbonate. The filtrate containing the product was spin-dried and purified by silica gel column eluting with dichloromethane to give the title product as a yellow solid, yield 213 mg, yield 85%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methyl-3-nitrobenzonitrile, its application will become more common.

Reference:
Patent; Tianjin Normal University; Liu, Guiyan; Wang, Jianhui; Yin, Maocong; Liu, Chengxin; (11 pag.)CN106397317; (2017); A;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, 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 77326-36-4, Application In Synthesis of 2-Amino-6-fluorobenzonitrile

Example 134b 3-(3-amino-2-cyanophenoxy)-N-isopropyl-2,2-dimethylpropanamide To a solution of 3-hydroxy-N-isopropyl-2,2-dimethylpropanamide (Example 134c, 5.12 g, 32.15 mmol) in dry THF (100 mL) was added portion-wise NaH (60% in mineral oil, 1.41 g, 35.37 mmol) at 0 C. under nitrogen. The reaction mixture was stirred at 0 C. for about 30 minutes until bubbling ceased. 2-Amino-6-fluorobenzo-nitrile (4.38 g, 32.15 mmol) was added and the solution stirred at 80 C. overnight. The reaction mixture was quenched slowly with water at 0 C., and concentrated under reduced pressure. The residue was taken up in EtOAc and washed consecutively with brine and water, dried over Na2SO4 and concentrated. The residue was purified by re-crystallization from EtOAc/hexane to give the title compound as a white crystalline solid (4.4 g, 50%). 1H NMR (400 MHz, CDCl3) delta 1.18 (d, J=6.8 Hz, 6H), 1.32 (s, 6H), 3.94 (s, 2H), 4.04-4.12 (m, 1H), 4.43 (s, 2H), 5.98 (d, J=6.8 Hz, 1H), 6.21 (d, J=8.0 Hz, 1H), 6.32 (d, J=8.0 Hz, 1H), 7.21 (t, J=8.0 Hz, 1H). MS 276 (MH+).

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; SENOMYX, INC.; Tachdjian, Catherine; Karanewsky, Donald; Tang, Xiao Qing; Liu, Hanghui; US2015/245642; (2015); 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. 10412-93-8, name is N-Benzyl-2-cyanoacetamide, A new synthetic method of this compound is introduced below., category: nitriles-buliding-blocks

EXAMPLE 6 Synthesis of Cyanoester G Cinnamaldehyde E (11.0 g; corrected with the HPLC purity) was dissolved in methanol (500 g). The solution was filtered over a nutsch, which is rinsed with methanol (80 g). At 20-25 C., intermediate F (8.5 g) was added in one portion to the methanolic solution followed by the addition of piperidine (9.1 g) in several portions. The deep red solution was stirred for at least 3 hours and an in-process control performed. Upon total conversion of starting material, 370 g of methanol was distilled off at 4045 C. To the resulting residue was added 16.6 g of HCl (32%) and water (150 g). The color changed from red to yellow and the product precipitated out of solution provided that pH was between 1 and 1.3. The suspension was then cooled to 0-5 C. and stirred for at least 2-3 hours (up to 20 hours) to maximize the yield. The suspension was then filtered via a nutsch and the residue rinsed with water (25 g) to yield 15.1 g of G. The wet G (15 g) was then suspended in acetonitrile (600 g) and heated to 80-82 C. for 1 h. The suspension was then cooled to 0-5 C. and stirred for at least 3 h. The wet material was separated with a nutsch and rinsed twice with a mixture of ethanol (10 g) and water (20 g). Final drying in the vacuum dryer at 45 C. yields 10.2 g of yellowish G in an overall yield of 56% (over two steps).

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; LymphoSign Inc.; US2005/33090; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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.

Step A To a solution of 2-(3-methoxyphenyl)acetonitrile (2 g; 13.59 mmol) in 13 mL of dry DCM) cooled at 0 C. under nitrogen atmosphere, a 1M solution of BBr3 in DCM (28.54 mmol; 28.54 mL) is slowly added dropwise. The mixture is stirred at room temperature for 20 hours. The reaction mixture is then poured into ice, water is added and the organic phase is extracted three times with DCM, washed with brine and dried over anhydrous Na2SO4. After evaporation, the crude mixture is chromatographed on silica gel using PE/EtAc (80/20) as an eluant, yielding 1.28 g (71%) of 2-(3-hydroxyphenyl)acetonitrile.

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; NEWRON PHARMACEUTICALS S.P.A.; Pevarello, Paolo; US2014/88074; (2014); A1;,
Nitrile – Wikipedia,
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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. 7357-70-2, name is 2-Cyanothioacetamide, A new synthetic method of this compound is introduced below., SDS of cas: 7357-70-2

40.4 g (171.0 mmol) of the compound from Example 37A and 34.2 g (342.0 mmol) of cyanothioacetamide were initially charged in 700 ml of ethanol. 34.5 g (342.0 mmol) of 4-methyl morpholine were added, and the reaction mixture was heated under reflux with stirring for 3 h. After cooling to RT, the mixture was stirred at this temperature for a further 16 h. The resulting precipitate was filtered off with suction, washed with about 100 ml of ethanol and dried in a drying cabinet. The product was used without further purification for the subsequent reactions.Yield: 19.5 g (29% of theory)1H-NMR (400 MHz, DMSO-d6): delta=7.63-7.31 (br s, 2H), 7.41 (d, 2H), 7.09 (d, 2H), 4.49-4.38 (m, 1H), 4.15-3.99 (m, 2H), 3.78 (dd, 1H), 3.66 (dd, 1H), 2.77-2.68 (br s, 1H), 1.37 (s, 3H), 1.32 (s, 3H).LC-MS (Method 9): Rt=1.95 min; MS (ESIpos): m/z=424 [M+H+CH3CN]+.

The synthetic route of 7357-70-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nell, Peter; Vakalopoulos, Alexandros; Suessmeier, Frank; Albrecht-Kuepper, Barbara; Zimmermann, Katja; Keldenich, Joerg; Meibom, Daniel; US2011/3845; (2011); 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. 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 3759-28-2

Step B 4-Cyano-N-(1,1-dimethylethoxy)carbonyl-4-(2-cyanophenyl)piperidine A solution of bis(2-chloroethyl)-N-(1,1-dimethylethoxy)carbonyl amine (19 g, 78 mmol) and homophthalonitrile (8.6 g, 60 mmol) and cesium carbonate (79 g, 241 mmol) was stirred at 60 C. for 12 hours. The solution cooled to room temperature and diluted with 500 ml EtOAc and washed with saturated aqueous NaHSO4 and saturated aqueous NaCl. The solution was dried over Na2SO4, concentrated in vacuo, and purified by PCTLC (30% EtOAc in Hexane) to afforded 4-cyano-N-(1,1-dimethylethoxy)carbonyl-4-(2-cyanophenyl) piperidine as a yellow/orange oil. 1H NMR (CDCl3): delta7.81-7.79 (d, 2H), 7.67-7.65 (m, 2H), 7.51-7.47 (m, 1H), 4.31 (br s, 2H), 3.26 (br s, 2H), 2.33-2.20 (m, 4H), 1.48 (s, 9H).

The synthetic route of 3759-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6319932; (2001); B1;,
Nitrile – Wikipedia,
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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. 935-02-4, name is 3-Phenylpropiolonitrile, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C9H5N

4.4.1 (Z+E)-3-(3-Methyl-2-selenoxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile (4a) To a mixture of acetylene 2 (64.0 mg, 0.5 mmol) and Se (40.0 mg, 0.5 mmol) in MeCN (1 mL) was added 1-methylimidazole (1a; 41.0 mg, 0.5 mmol) in MeCN (1 mL). The mixture was stirred at 82 C for 5 h. After cooling to 20-25 C, the solvent was removed and column chromatography afforded selone (Z)-4a (46 mg, 39%) as a yellow microcrystalline powder, mp 208-209 C (ethanol). Initial imidazole 1a was recovered (7 mg, conversion was 83%). Initial Se was recovered (20 mg, conversion was 50%). Z:E-isomers ratio was 5:1 [(E)-isomer, 5%, data 1H NMR]. (Z)-Isomer: 1H NMR (400.13 MHz, CDCl3): delta=7.50-7.27 [m, 5H, Ho,m,p from C(6)-Ph], 7.07 (s, 1H, 4-H), 6.98 (s, 1H, 5-H), 6.12 (s, 1H, 7-H), 3.76 (s, 3H, N-CH3) ppm. 13C NMR (100.62 MHz, CDCl3): delta=159.2 (C-2), 154.9 (C-6), 132.4 [Ci from C(6)-Ph], 132.0 [Cp from C(6)-Ph], 129.3 [Cm from C(6)-Ph], 127.0 [Co from C(6)-Ph], 121.7 (C-4), 119.3 (C-5), 114.5 (CN), 97.7 (C-7), 37.5 (N-CH3) ppm. (E)-Isomer: 1H NMR (400.13 MHz, CDCl3): delta=7.50-7.45 [m, 5H, Ho,m,p from C(6)-Ph], 6.94 (s, 1H, 7-H), 6.90 (s, 1H, 4-H), 6.65 (s, 1H, 5-H), 3.73 (s, 3H, N-CH3) ppm. IR (KBr): 2222 (CN), 1622 (C=C), 1368 (C=Se) cm-1. Anal. Calcd for C13H11N3Se (288.21): C, 54.18; H, 3.85; N, 14.58; Se, 27.40. Found: C, 54.50; H, 3.99; N, 14.52; Se, 27.07.

According to the analysis of related databases, 935-02-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Belyaeva, Kseniya V.; Andriyankova, Ludmila V.; Nikitina, Lina P.; Mal’Kina, Anastasiya G.; Afonin, Andrei V.; Ushakov, Igor A.; Bagryanskaya, Irina Yu.; Trofimov, Boris A.; Tetrahedron; vol. 70; 5; (2014); p. 1091 – 1098;,
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Application of 64248-62-0,Some common heterocyclic compound, 64248-62-0, name is 3,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

Step 1: 3,4-Difluorobenzonitrile (30 g, 0 · 22 mol) was placed in a 500 mL autoclave, and an ammonia gas of 37 · 4 g (2.2 mol) was introduced. Then, the temperature was raised to 110 C for 24 hours, sampled, and the reaction was monitored by liquid chromatography to a normalized content of 0.5%. After cooling to room temperature, pressure was added, toluene (120 mL) was added, the temperature was raised to 60 C for 0.5 h, then the temperature was lowered to 0 C, filtered, and the filter cake was mixed with water (150 mL X 3 ), filtered, and filtered cake 40. (: Vacuum drying to give 2- fluoro-4-aminobenzonitrile 27.9 g (yield 95%; purity >99%, off-white solid, melting point 70-72 C). It is 3-fluoro-4-aminobenzonitrile.

The synthetic route of 64248-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jinkai (Liaoning) Chemical Co., Ltd.; Yang Xiaoge; Wang Yongcan; Wang Xiuying; Jiang Zhipeng; Zhang Jinxin; Song Tongji; (13 pag.)CN109678741; (2019); 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 52798-01-3 as follows. Product Details of 52798-01-3

To a solution of methyl (4-cyanophenyl)acetate (4.00 g, 27.8 mmol) in MeOH (20 mL), hydroxylamine hydrochloride (3.17 g, 45.7 mmol) and NaHCO3 (3.84 g, 45.7 mmol) is added. The suspension is stirred at 60 C. for 18 h before it is filtered and the filtrate is concentrated. The residue is dissolved in DCM, washed with water followed by brine, dried over MgSO4, filtered, concentrated and dried to give methyl [4-(N-hydroxycarbamimidoyl)-phenyl]-acetate (3.67 g) as a colourless oil; LC-MS: tR=0.50 min, [M+1]+=209.05.

According to the analysis of related databases, 52798-01-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Actelion Pharmaceuticals Ltd.; US2010/63108; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 623-26-7, name is Terephthalonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C8H4N2

Crude p-cyanobenzylamine was synthesized in accordance with the process described in Japanese Unexamined Patent Publication (kokai) No. 9-40630 as follows. Into a 100 ml autoclave, methanol (30 ml) and sponge nickel (R-2400, product of W.R. Grace & Co.) (1.0 g) were placed, and the internal pressure of the autoclave was elevated to 1.0 MPa by introducing hydrogen. The mixture contained in the autoclave was stirred while heating at 150 C. for one hour. Terephthalonitrile (5.0 g) and sodium hydroxide (0.1 g) were introduced into the reactor, and the internal pressure was elevated to 0.5 MPa at ambient temperature while introducing hydrogen. Under monitoring of the hydrogen absorbing rate, when the hydrogen pressure was dropped to 0.1 MPa, the pressure was elevated again to 0.5 MPa. This pressure control operation was repeated. Reaction was terminated when the hydrogen absorption ratio reached 115% of the theoretical value. From the thus-obtained reaction mixture, methanol was removed through distillation. The resultant mixture was subjected to a further distillation at a high temperature under a reduced pressure, thereby removing crude p-cyanobenzylamine. Through high-performance liquid chromatographic analysis of the distillate, the p-cyanobenzylamine content and the p-xylylenediamine content were found to be 93 mass % and 7 mass %, respectively.

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; Showa Denko K.K.; US6392083; (2002); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts