Tag: M.W=100-200

Synthetic Route of 3672-47-7,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.

General procedure: Ketonitrile 5 (100 mmol) was added to 15% aqueous NaOH solution(100 mL) followed by hydroxylamine (200 mmol). The resulting mixture was heated at reflux for 14 h, cooled down to r.t., theresulting precipitate was isolated by filtration and crystallized from isopropyl alcohol.

The synthetic route of 3672-47-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Krasavin, Mikhail; Korsakov, Mikhail; Zvonaryova, Zhanna; Semyonychev, Evgenii; Tuccinardi, Tiziano; Kalinin, Stanislav; Tanc, Muhammet; Supuran, Claudiu T.; Bioorganic and Medicinal Chemistry; vol. 25; 6; (2017); p. 1914 – 1925;,
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Reference of 64248-62-0, The chemical industry reduces the impact on the environment during synthesis 64248-62-0, name is 3,4-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

40 mL of N,N-dimethylformamide was placed in a 250 mL four-necked flask.R-(+)-2-(4-hydroxyphenoxy)propionic acid butyl ester 34g (0.14 mol),3,4-difluorobenzonitrile 24g (0.168mol),Phase transfer catalyst 18-crown-6 0.15g, TEBA 0.15g,With stirring, 58 g (0.42 mol) of potassium carbonate was added, and a large amount of bubbles were generated;Then the temperature was raised to 85-90 C, the reaction was kept for 3 hours, and the sample was analyzed by HPLC.R-(+)-2-(4-hydroxyphenoxy)propionic acid butyl ester <0.5%, the reaction was completed.Filtration, distilling off the solvent under reduced pressure, and cooling to room temperature with 150 mL of water.The temperature is raised to 60-70 C, the mixture is completely dissolved, and the layer is allowed to stand.Wash with 100 mL of water and de-dissolve to dryness to give an oil.That is, the original drug of cyhalofop-butyl ester 49.5g, the yield: 98.9%, the content: 98.0%,Optical 97.2%. 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-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see. Reference:
Patent; Jiangsu Zhongqi Technology Co., Ltd.; Zhang Sheng; Zhang Pu; Wang Yuchi; Chen Wen; Wang Fengyun; Hou Yuanchang; (6 pag.)CN109651140; (2019); A;,
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Related Products of 16588-02-6, 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. 16588-02-6 name is 2-Chloro-5-nitrobenzonitrile, 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.

General procedure: In a typical experiment, p-CNB (1 g, 6.35 mmol), CuI (0.635 mmol),commercial 25% aqueous NH3 solution (10 mL, NH3/p-CNB molar ratio21/1) were loaded into a 50 mL stainless steel reactor and sealed. Thematerial of the autoclave used is AISI 316 L, for which the compositionis Cr 16-18%, Ni 10-14%, Mo 2-3%, MnQ2%, Si Q1%, CQ0.03%,SQ0.03%, PQ0.045%, and the other part is Fe. After being heated to200 C, the reaction was conducted while stirring with a magneticstirrer (1200 rpm). The pressure of the vapor phase (NH3 and H2O) wasabout 3 MPa at the reaction temperature. After stirring for 1 h, the reactorwas cooled to room temperature and the reaction mixture wasseparated by centrifugation. The solid substrate and product were dissolvedin ethanol and analyzed by a gas chromatograph (Shimadzu GC-2010) equipped with a capillary column (Rtx-5 capillary column: 30m¡Á0.25mm ¡Á0.25 Tm, carrier: N2) and a flame ionization detector(FID) and gas chromatograph-mass spectrometer (GC-MS, Agilent 5890,HP-5). o-Xylene was used as an internal standard for quantitativeanalysis. The liquid phase was also analyzed by gas chromatograph andno p-CNB or p-NAN were detected. The carbon balance was near 99%and trace amount of other unidentified byproducts were observed.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-nitrobenzonitrile, and friends who are interested can also refer to it.

Reference:
Article; Li, Yan; Shi, Ruhui; Lin, Weiwei; Cheng, Haiyang; Zhang, Chao; Arai, Masahiko; Zhao, Fengyu; Molecular catalysis; vol. 475; (2019);,
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Some common heterocyclic compound, 5332-06-9, name is 4-Bromobutanenitrile, molecular formula is C4H6BrN, 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. Recommanded Product: 4-Bromobutanenitrile

Preparation of 4-[2-(4-Nitro-phenyl)-6-oxo-4-thioxo-6H-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-5-yl]-butyronitrile (Compound 35) A solution of 4-bromo-butyronitrile (300 mg, 2.02 mmol) and sodium azide (263 mg, 4.05 mmol) in acetone (10 ml) is refluxed for 12 hours under nitrogen atmosphere, cooled to room temperature, filtered, and the solvent is removed under vacuum to give 4-azido-butyronitrile as a colorless liquid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5332-06-9, its application will become more common.

Reference:
Patent; Gelder, Joel M. Van; Klein, Joseph Y.; Basel, Yochai; Reizelman, Anat; Tchilibon, Susanna; Mouallem, Orly; US2008/39456; (2008); A1;,
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Electric Literature of 42872-83-3, These common heterocyclic compound, 42872-83-3, name is 2-Bromo-5-methylbenzonitrile, 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: Ni NPs/HT (0.05 g) is placed in a heavy-walled pressure tube, followed by the addition of water (4 ml) and benzonitrile (1 mmol), and the reaction mixture is vigorously stirred at 120 C in an oil bath for the specified time in tables. The progress of the reaction in each case was monitored by TLC analysis. After completion of the reaction, the reaction mixture is extracted with ethyl acetate, after the extraction, the catalyst is removed by filtration, and the filtrate is cooled to 0 C, and white crystals are precipitated from the filtrate. The crystalline product was obtained by simple filtration and dried in vacuo at room temperature to give analytically amide product. In cases where the product not precipitated out, the reaction mixture was extracted with ethyl acetate, subsequent purification by column chromatography on silica gel provided amide product.

The synthetic route of 42872-83-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Subramanian, Thirumeni; Pitchumani, Kasi; Catalysis Communications; vol. 29; (2012); p. 109 – 113;,
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Adding a certain compound to certain chemical reactions, such as: 3215-64-3, name is 2-(2,6-Dichlorophenyl)acetonitrile, 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 3215-64-3, Quality Control of 2-(2,6-Dichlorophenyl)acetonitrile

Example 21Example for Compound 21Into a 1 L flask was weighed 25.0 g (134 mmol) of 2,6-dichlorophenylacetonitrile and 250 mL of anhydrous THF. The resulting solution was cooled to -70 C. and 134 mL of 1.0 M potassium tert-butoxide (1.0 M) in THF was added followed by 8.4 mL of iodomethane (1.0 eq). The reaction was stirred at -70 C. for 1 h then was allowed to warm to room temperature over 3 h. The reaction was concentrated in vacuo to remove THF then was washed into a separatory funnel with ethyl acetate and 1 M HCl. The ethyl acetate was separated, washed with bisulfite, brine, was dried (Na2SO4), and concentrated in vacuo. The residue was purified by silica gel flash chromatography (Biotage, 300 g SiO2, gradient elution from 100% hexanes to 10% ethyl acetate over 1 h). Appropriate fractions were combined and concentrated in vacuo to afford the desired product as a colorless oil, 99% pure by GC, yield: 12.2 g (45%). 1H NMR (CDCl3, 400 MHz) delta 7.36 (d, J=8 Hz, 2H), 7.22 (t, J=8 Hz, 1H), 4.84 (q, J=7 Hz, 1H), 1.07 (d, J=7 Hz, 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, 2-(2,6-Dichlorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; EXELIXIS PATENT COMPANY LLC; Busch, Brett B.; Stevens, JR., William C.; Kick, Ellen K.; Zhang, Haiying; Bollu, Venkataiah; Martin, Richard; Mohan, Raju; US2015/299136; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 147754-12-9, name is 4-Fluoro-2-methylbenzonitrile, 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 147754-12-9, SDS of cas: 147754-12-9

The 4- Fluoro-2-methylbenzonitrile (compound B)(2g,14.8mmol) , N-Bromosuccinimide(NBS) (2.64g,15mmol) , AzobisisobutyronitrileAIBN(100mg) dissolved in CCl4 , Under theprotection of nitrogen gas it was heated to reflux for 2 h. Cooled toroom temperature, filtered to remove solids, concentrated to obtain crude oil, Which was used directly in the nextstep without purification.

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; Hebei Guolong Pharmaceutical Co.,Ltd; Yin, Dian Shu; Du, Yu Min; Wang, yabo; Wei, Sai Li; Shang, weiding; Zhao, yisha; Yan, Yong-Na; Zhang, qingjiang; Wang, Chun FA; (13 pag.)CN105541793; (2016); A;,
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Reference of 1009-35-4, 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 1009-35-4 as follows.

To a suspension of sodium hydride (60’Yo, 0.58 g) in THF (2 ml), wasadded 4-fluoro-3-nitro-benzonitrile (1.33 g, 8.0 rnmol) and 2-arnino-5-methylthiophene-3-carbonitrile (1. i 0 g, 8.0 rnmol) in THF (1 0 ml), dropwise. The mixture was stirred at room temperature overnight. Two more batches of sodium hydride(60percent, 0.50 g and OA g) were added over the next 6 hours. After stirring for 3 days,the mixture was poured into ice-water (20 ml) and acidified to pH 3 with 6Nhydrochloric acid (7 ml). The precipitate was filtered and washed with water. Thesolid was extracted with dichloromethane (35 ml). The solution was concentrated toa solid, and used in the next step without additional purification. LC-MS: rn/z 285(M+1 ), 307 (M+23). 1H NMR (CDCb, 400 MHz): i5 (ppm) 9.76 (s, 1 H), 8.59 (s, 1 H),7.70 (d, 1H), 7.14 (d, 1H), 6.87 (s, 1H), 2.52 (s, 1H).

According to the analysis of related databases, 1009-35-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ORTHO-CLINICAL DIAGNOSTICS, INC; JANSSEN PHARMACEUTICA NV; HRYHORENKO, Eric; SANKARAN, Banumathi; DECORY, Thomas, R.; TUBBS, Theresa; COLT, Linda; REMMERIE, Bart, M.; SALTER, Rhys; DONAHUE, Matthew, Garrett; GONG, Yong; WO2014/31656; (2014); A1;,
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Reference of 6136-68-1, 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. 6136-68-1 name is 3-Acetylbenzonitrile, 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.

9.40 g (64.757 mmol) 3-cyano-acetophenone, 40.00 g (518.941 mmol) ammonium acetate and 10.00 g (186.951 mmol) ammonium chloride are placed in methanol. The mixture is stirred for 16 hours at 40 C. 2.90 g (46.149 mmol) sodium cyanoborohydride are added, then the mixture is stirred for another 16 hours. The reaction mixture is adjusted to pH3 with glacial acetic acid, then the methanol is evaporated down. On cooling a precipitate settles out. This is suction filtered. The filtrate is made alkaline with conc. sodium hydroxide solution, the precipitate thus formed is suction filtered. The filtrate is extracted with diethyl ether, the combined organic phases are dried and evaporated to dryness. The residue is purified by vacuum distillation. Yield: 1.10 g (=12% of theoretical)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Acetylbenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2006/116370; (2006); A1;,
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Application of 7251-09-4, 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 7251-09-4 as follows.

Step 1: Synthesis of 4-((4-amino-8-bromoquinazolin-2-yI)amino)-2-methoxybenzonitrile hydrochloride (Compound 3a) Compound 3a [0255] A mixture of 8-bromo-2-chloroquinazolin-4-amine (259 mg, 1 mmol, Ark Pharm Inc, AK-28702) and 4-amino-2-methoxybenzonitrile (222 mg, 1.5 mmol, Ark Pharm Inc, AK-77827) in isopropanol (7 mL) was heated in microwave at 180 C for 8 hours. The reaction mixture was cooled down to room temperature and the solid product was filtered off and washed with cold isopropanol and then with diethyl ether and hexane to afford the compound 3a as the HC1 salt. NMR (400 MHz, DMSO- /6) delta 8.24 (d, J = 8.1 Hz, 1H), 8.07 (d, J= 7.6 Hz, 1H), 7.59 (d, J= 8.5 Hz, 1H), 7.42 (dd, J = 8.6, 1.9 Hz, 1H), 7.37 – 7.04 (m, 5H), 3.99 (s, 3H). LCMS (m/z) 370.3 [M+H], Tr = 2.43 min (LCMS method 2).

According to the analysis of related databases, 7251-09-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD SCIENCES, INC.; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY OF THE AS CR, V.V.I.; JANSA, Petr; SIMON, Tetr; LANSDON, Eric; HU, Yunfeng, Eric; BASZCZYNSKI, Ondrejj; DEJMEK, Milan; MACKMAN, Richard, L.; (185 pag.)WO2016/105564; (2016); A1;,
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