Month: August 2021

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. 15666-97-4, name is Octyl 2-cyanoacetate, A new synthetic method of this compound is introduced below., Computed Properties of C11H19NO2

d) In a 20 mL one-necked flask,Compound 2 (0.15 g, 0.1 mmol)And n-octyl cyanoacetate (0.2 g, 1 mmol) were dissolved in 20 mL of dry chloroform,Piperidine (0.1 mL) was added under argon,Followed by heating to 60 C for 24 h.After the reaction is over,The mixture was poured into water,Extracted with dichloromethane,The organic phase was collected and dried to give the crude product,And the product was separated by silica gel column using petroleum ether: dichloromethane (2: 1 by volume)Recrystallization from chloroform and methanol gave the dark red solid product NDFP-CNCOO (30 mg, yield: 14.6%),The synthetic compound NDFP-CNCOO is characterized as follows:

The synthetic route of 15666-97-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Central South University; Peng Hongjian; Luan Xiangfeng; Feng Liuliu; Li Hang; Zou Yingping; (11 pag.)CN106939013; (2017); A;,
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Nitriles – Chemistry LibreTexts

Reference of 1813-33-8, 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. 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of 2-chloro-4-(trifluoromethyl)-benzonitrile (1.00 mmol) and appropriate thiol (RSH, 3.00 mmol),18-crown-6-ether (cat.) and potassium carbonate (2.00 mmol)were dissolved in acetonitrile (3 ml). The mixture was refluxedfor 12 h and then cooled to ambient temperature. The mixturewas quenched by adding water and extracted with EtOAc.Extracted organic compound was dried over MgSO4, filtered, andconcentrated in vacuo. The residue was purified by flash columnchromatography on silica gel using EtOAc/hexane (1:4) eluantcondition. (RSH = CH3CO2(CH2)2SH for 42).

The synthetic route of 2-Chloro-4-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ann, Jihyae; Jung, Aeran; Kim, Mi-Yeon; Kim, Hyuk-Min; Ryu, Hyungchul; Kim, Sunjoo; Kang, Dong Wook; Hong, Sunhye; Cui, Minghua; Choi, Sun; Blumberg, Peter M.; Frank-Foltyn, Robert; Bahrenberg, Gregor; Stockhausen, Hannelore; Christoph, Thomas; Lee, Jeewoo; Bioorganic and Medicinal Chemistry; vol. 23; 21; (2015); p. 6844 – 6854;,
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Electric Literature of 1897-52-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 1897-52-5 name is 2,6-Difluorobenzonitrile, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Cyano-(2-cyano-3-fluoro-phenyl)-acetic acid ethyl ester.A mixture of cyanoacetic acid ethyl ester (26.7 mL, 251 mmol), 2,6-difluorobenzonitrile (33.2 g, 239 mmol) and potassium carbonate (82.5 g, 597 mmol) in dimethyl sulfoxide (120 mL) was stirred at +55C for 16 hours and poured into ice-water mixture (ca. 400 mL). It was acidified with cone. aq. HCl with caution (CO2 evolution) and extracted with ethyl acetate (600 ml). The organic phase was washed with brine (100 mL) and evaporated to give 55.1 g of a pale yellow solid that was used in the next step without further purification. 1H NMR (500 MHz, CDCl3): 1.35 (t, J=7.0 Hz, 3H), 4.34 (m, 2H), 5.13 (s, IH), 7.33 (t, J=8.4 Hz, IH), 7.57 (d, J=7.9 Hz, IH), 7.33 (dd, J=7.9 Hz, J=13.9 Hz, IH).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Difluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; H. LUNDBECK A/S; WO2009/156339; (2009); A1;,
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Application of 654-70-6,Some common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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.

Thionyl chloride (46.02 g, 0.39 mol) was added dropwise to a cooled solution (less than 4 C) of (/?)-3-bromo-2-hydroxy-2-methylpropanoic acid (51.13 g, 0.28 mol) in 300 mL of THF under an argon atmosphere. The resulting mixture was stirred for 3 h under the same condition. To this was added Et3N (39.14 g, 0.39 mol) and stirred for 20 min under the same condition. After 20 min, 5-amino-2- cyanobenzotrifluoride (40.0 g, 0.21 mol), 400 mL of THF were added and then the mixture was allowed to stir overnight at rt. The solvent was removed under reduced pressure to give P-75003-PC a solid which was treated with 300 mL of H20, extracted with EtOAc (2 X 400 mL). The combined organic extracts were washed with saturated NaHCC>3 solution (2 X 300 mL) and brine (300 mL). The organic layer was dried over MgS04 and concentrated under reduced pressure to give a solid which was purified from column chromatography using CH2Cl2/EtOAc (80:20) to give a solid. This solid was recrystallized from CH2Cl2/hexane to give 55.8 g (73.9%) of (2/?)-3-bromo-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2- methylpropanamide as a light-yellow solid. *H NMR (CDC13/TMS) delta 1.66 (s, 3H, CH3), 3.11 (s, 1H, OH), 3.63 (d, / = 10.8 Hz, 1H, CH2), 4.05 (d, / = 10.8 Hz, 1H, CH2), 7.85 (d, / = 8.4 Hz, 1H, ArH), 7.99 (dd, / = 2.1, 8.4 Hz, 1H, ArH), 8.12 (d, / = 2.1 Hz, 1H, ArH), 9.04 (bs, 1Eta, NH). Calculated Mass: 349.99, [Mu-Eta]” 349.0. M.p.: 124-126 C.

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

Reference:
Patent; GTX, INC.; DALTON, James, T.; GOSNELL, Matthew; WO2013/67170; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 5332-06-9, name is 4-Bromobutanenitrile, 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 5332-06-9, Quality Control of 4-Bromobutanenitrile

To a solution of 4-bromobutanenitrile (1.50 g, 10.17 mmol) in dimethylformamide (20 ml) were added 1-(4-chlorophenyl)piperazine (2.0 g, 10.17 mmol)and potassium carbonate (2.81 g, 20.34 mmol) at room temperature and the reaction mixture was stirred for 3 h at same temperature. The progress of the reaction was monitored by TLC. The reaction mixture was diluted with water (50 ml) and the aqueous layer was extracted with ethyl acetate (3 x 50 ml). Thecombined organic layer was dried over anhydrous sodium sulphate. The solvent in the organic layer was removed under reduced pressure to obtain a crude product, which was purified by column chromatography over silica gel (100-200 mesh) using 10% ethyl acetate in hexane to yield the title compound (2.32 g, 86% yield).

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, 4-Bromobutanenitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LUPIN LIMITED; JANA, Gourhari; KURHADE, Sanjay, Pralhad; JAGDALE, Arun, Rangnath; KUKREJA, Gagan; SINHA, Neelima; PALLE, Venkata, P.; KAMBOJ, Rajender, Kumar; WO2014/9872; (2014); A1;,
Nitrile – Wikipedia,
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Related Products of 939-79-7, These common heterocyclic compound, 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, 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.

General procedure: To a stirred solution of 18(166.51 mmol), 23 (166.51 mmol) or 27 (166.51 mmol) in CCl4 (350 mL) were added NBS (199.82 mmol) and benzoyl peroxide (16.65 mmol) under nitrogen atmosphere. The mixture was heated at reflux temperature for 13 h and then cooled to room temperature. The reaction mixture was filtered and then washed with CH2Cl2 (2 × 400 mL). The combined organic layers waswashed with water (200 mL), dried over anhydrous Na2SO4, and then evaporated to dryness under reduce pressure. The residue was purified by MPLC on silica gel to afford the titled compounds.

The synthetic route of 939-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jin, Cheng Hua; Krishnaiah, Maddeboina; Sreenu, Domalapally; Subrahmanyam, Vura Bala; Park, Hyun-Ju; Park, So-Jung; Sheen, Yhun Yhong; Kim, Dae-Kee; Bioorganic and Medicinal Chemistry; vol. 22; 9; (2014); p. 2724 – 2732;,
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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. 123-06-8, name is Ethoxymethylenemalononitrile, A new synthetic method of this compound is introduced below., Computed Properties of C6H6N2O

Step 1 (0885) [00206] To a mixture of EpsilonbetaNu (1.39 ml_, 10 mmol) and cyclohexylhydrazine hydrochloride (1.51 g, 10 mmol) in EtOH (35 ml_) was added ethoxymethylenemalononitrile (1.22 g, 10 mmol) portion wise. The reaction mixture was heated at reflux for 5 hours, then cooled to room temperature and concentrated in vacuo. The residue was taken up in EtOAc (50 ml_) and washed with water (2 chi 25 ml_). The organic phase was dried over MgSCU, filtered and concentrated in vacuo to return 5-amino-1-cyclohexyl-pyrazole-4-carbonitrile (1.95 g, 103%) as an orange solid which was used without further purification. 1 H NMR (300 MHz, CDC ) delta 7.49 (s, 1 H), 4.45 (s, 2H), 3.77 (tt, J = 1 1.2, 4.2 Hz, 1 H), 1.88 (ddt, J = 17.4, 1 1.4, 5.4 Hz, 6H), 1.83-1.65 (m, 1 H), 1.49-1.32 (m, 1 H), 1.38-1.15 (m, 2H).

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; CANCER RESEARCH TECHNOLOGY LIMITED; JORDAN, Allan; NEWTON, Rebecca; (174 pag.)WO2017/178844; (2017); A1;,
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. 3218-50-6, name is 2,5-Dichlorobenzyl cyanide, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

To a suspension of NaH (60% w/w suspension in paraffin oil) (14.19 g, 354.76 mmol) in dimethyl sulfoxide (300 mL), was added (2,5-dichloro-phenyl)-acetonitrile (197) (30 g, 161.256 mmol) and 1,4-dibromobutane (19.34 mL, 161.26 mmol) by dissolving in dimethyl sulfoxide-ether (1:1, 600 mL) dropwise at 0 C. The reaction mixture was stirred at room temperature for 1 h. Silica thin layer chromatography was conducted (10% ethyl acetate in hexane, Rf=0.8). After completion of the reaction, water (500 mL) and 10% HCl solution (200 mL) were added and the mixture was extracted with ethyl acetate. The organic part was dried, and evaporated to get a crude residue, which was purified with silica gel (normal, 100-200 mesh) column chromatography using a gradient eluent of 2 to 10% ethyl acetate in hexane to get pure ( 198) (26.5 g, 68.44%) as a white solid. [0803] GCMS: 239 (M).

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 3218-50-6.

Reference:
Patent; Wolkerstorfer, Andrea; Szolar, Oliver; Handler, Norbert; Buschmann, Helmut; Cusack, Stephen; Smith, Mark; So, Sung-Sau; Hawley, Ronald Charles; Sidduri, Achyutharao; Zhang, Zhuming; US2014/194431; (2014); A1;,
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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 17823-40-4 as follows. Quality Control of 4-Bromo-2,3,5,6-tetrafluorobenzonitrile

A mixture of Compound G (6 50 g, 14.93 mmol), 4-bromo-2,3,5,6-tetrafluorobenzonitrile (3.86 g, 15.23 mmol), Pd(PPh3)4 (871 mg, 0.747 mmol), potassium carbonate (6 21 g, 44.79 mmol) in degassed deionized water (20 mL) and degassed THF (60 mL) solution was stirred at 80 C under a nitrogen atmosphere for 24 h. After cooled to room temperature, the reaction mixture was added methanol (400 mL) and filtered. The obtained solid was sequentially rinsed by water (20 mL) and methanol (20 mL), and eventually dried in vacuo. The obtained residue veas purified by column chromatography on silica gel using 3: 1 (v/v) hexane/toluene as eluent to afford a white solid (4 80 g, 66.6%). H NMR (500 MHz, CDCb, d): 8 94 (d, ./= 6.5 Hz, 2H), 8 80 (d, J= 7.0 Hz, 41 }. 7.70 (d, J= 8.5 Hz, 21 }. 7.66-7.59 (m, 6H); APCI-MS m/z: 483.4 ML

According to the analysis of related databases, 17823-40-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KYULUX, INC.; CHENG, Shuo-Hsien; CHO, Yong, Joo; SUZUKI, Yoshitake; YANG, Yu, Seok; NOTSUKA, Naoto; ENDO, Ayataka; KAKIZOE, Hayato; YOSHIZAKI, Makoto; AGUILERA-IPARRAGUIRRE, Jorge; (264 pag.)WO2019/191665; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 40497-11-8, name is Ethyl 2,3-dicyanopropanoate, 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 40497-11-8, COA of Formula: C7H8N2O2

Example 11 Preparation of 5-aminopyrazole (VII) [0071] To 2,6-dichloro-4-trifluoromethyl aniline 230 g and acetic acid 150 ml was added 1.1 m of nitrosyl sulphuric acid over one hour at 30 C. and maintained at 30 C. for one more hour. Heat the mass to 50-55 C. over ½ hour and the absence of 2,6-dichloro-4-trifluoromethyl aniline was monitored. Cool the mass to 30 C., and the excess nitrosyl sulphuric acid was destroyed. [0072] The above diazotized mass was added to a mixture of 250 ml of acetic acid, 162 g ethyl-2,3-dicyanoproprionate and 425 ml water over 4-5 hours maintaining temperature 0-5 C. Further maintained at 0 C./2 hours, 5 C./1 hour, 10 C./1 hour, 15 C./1 hour. 800 ml water was added at 15 C. over ½ hour, extracted the solution with 3×250 ml methylene dichloride. Layers were separated. Dichloromethane layer was washed with 250 ml water, cooled the dichloromethane layer to 0 C. and washed with 250 ml 8N aq. NH3 under stirring for one hour. Layers were separated, dichloromethane layer was taken and NH3 gas was passed at 0-5 C. till free NH3 was observed on top of the condenser and maintained the reaction mass for 3-4 hours at 0-5 C. Then 250 ml water was added, stirred for ½ hour, layers were separated, extracted aq. layer with 2×100 ml dichloromethane, dichloromethane layer was dried with MgS04, dichloromethane layer was concentrated to dryness, to obtain 288 g of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethyl phenyl)-pyrazole of 98% purity.

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, Ethyl 2,3-dicyanopropanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gharda, Keki Hormusji; US2013/30190; (2013); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts