Author: Jessica.F

Application of 64248-62-0, 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 64248-62-0 as follows.

In a 500mL three-necked flask,Add 3,4-difluorobenzonitrile (50.0 g, 0.28 mol)And 200mL of absolute ethanol,Control temperature 0~5 C,Pass dry HCl gas to saturation,The reaction was kept for 30 hours, a large amount of white solid was precipitated, and suction filtration was applied. The filter cake was washed with 0 to 5 C anhydrous ethanol, and dried under vacuum to give (VI-11) 52.5 g, yield 65.9%.

According to the analysis of related databases, 64248-62-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; China Pharmaceutical University; Hefei Medical Engineering Pharmaceutical Co., Ltd.; Xu Yungen; He Guangwei; Liu Kun; Chu Zhaoxing; Zhu Qihua; Zhao Yan; Liu Weizhong; Wang Kui; Zhang Luyong; (26 pag.)CN108456152; (2018); A;,
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Related Products of 16588-02-6,Some common heterocyclic compound, 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, molecular formula is C7H3ClN2O2, 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.

Conc. HC1 (15.6 ml) was added dropwise to 2-chioro-5- nitrobenzonitrile (3.38 g, 18.5 mmol) and SnC12.2H20 (18.9 g, 83.9 mmol, 4.5 eq.) in isopropanol (35 ml). The mixture was heated at 120 C. for 2 h and then cooled to room temperature and made basic using aq. NaOH. The mixture wasextracted with dichloromethane, dried over Na2SO4 and filtered through silica gel. Concentration under reduced pressure gave 5-amino-2-chlorobenzonitrile (2.58 g, 91%).55?H NMR (300 MHz, CDC13): oe=3.90 (br. s, 2H), 6.79 (dm, 1H), 6.91 (m, 1H), 7.22-7.26 (m, 1H) ppm.

The synthetic route of 16588-02-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Maue, Michael; Kapferer, Tobias; Muehlthau, Friedrich August; Malsam, Olga; US9204645; (2015); B2;,
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Related Products of 52798-01-3, A common heterocyclic compound, 52798-01-3, name is Methyl (4-cyanophenyl)acetate, molecular formula is C10H9NO2, 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.

a. Methyl 2-(4-cyanophenyl)-tert.butyl malonate 1.7 g (0.01 mol) of methyl 4-cyanophenylacetate are dissolved in 30 ml tetrahydrofuran, 0.48 g (0.01 mol) of sodium hydride (60% in oil) are added in batches thereto and stirred for 15 minutes at 60 C. Then 1.5 ml (0.01 mol) of tert.butyl bromoacetate are added dropwise at ambient temperature. The reaction mixture is refluxed for 5 hours, cooled and poured onto water and extracted with methylene chloride. The combined organic extracts are dried and evaporated down. The residue is chromatographed on silica gel and eluted with petroleum ether/ethyl acetate (4:1). Yield: 1.5 g (52% of theory), Rf value: 0.7 (silica gel; petroleum ether/ethyl acetate=7:3).

The synthetic route of 52798-01-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim Pharma KG; US6114532; (2000); A;,
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Some common heterocyclic compound, 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, molecular formula is C7H5ClN2, 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. SDS of cas: 5922-60-1

Example 3: Synthesis of 6-chloro-2,4-diamino-quinazolineA mixture of 2-amino-5-chlorobenzonitrile (1.07 g, 7.0 mmol), chloro- formamidine hydrochloride (1.6 g, 14 mmol), sulfolane (0.5 ml) and dimethylsulfone(3 g) was heated at 165 0C for 30 minutes. Then, water (30 ml) was added to the reaction mixture. The pH was adjusted to 7-8 by the addition of a 33 percent aqueous ammonia solution in water. The precipitate was collected by filtration, washed with water and dried over P2O5, yielding the title compound as a yellowish solid (1.35 g, yield: 99 percent) which was characterized by its mass spectrum as follows: MS (m/z): 195([M+H]+, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5922-60-1, its application will become more common.

Reference:
Patent; GILEAD SCIENCES, INC.; WO2008/9077; (2008); A2;,
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These common heterocyclic compound, 63069-50-1, name is 4-Amino-3-fluorobenzonitrile, 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. SDS of cas: 63069-50-1

General procedure: 1.4.1. MethodAlj00243j A mixture of the amino aromatic or heteroaromatic starting material (1 eq), Ag2SO4 (1 eq) and 12 (1 eq) in EtOH is stirred at temperatures ranging from room temperature to 50C for a period which can vary from 1 h to approximately 16 h. The mixture is filtered, concentrated and diluted in an organic solvent. The organic mixture undergoes aqueous work up. The solvent is removed under reduced pressure and the residue is purified by flash column chromatography to yield the desired product.1.4.2. Illustrative example ofmethodAl: synthesis of 4-Amino-3-fluoro-5-iodo-benzonitrile (Int.4).N NH2 NI H2j00244j A mixture of 4-amino-3-fluorobenzonitrile (147 mmol), 12 (147 mmol) and Ag2SO4 (147 mmol) in EtOH (700 mL) was stirred at room temperature for 1.5 h. The mixture was filtered and concentrated. The residue was dissolved in EtOAc and washed (sat. Na2S2O3 x 3). The organic layer was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (Si02, 95:5 to 70:3 0 cyclohexane/EtOAc) to yield the desired product.

The synthetic route of 4-Amino-3-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALAPAGOS NV; MENET, Christel, Jeanne, Marie; MAMMOLITI, Oscar; BLANC, Javier; OR?ULIC, Mislav; RO?CIC, Maja; WO2015/110378; (2015); A1;,
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Electric Literature of 51632-29-2,Some common heterocyclic compound, 51632-29-2, name is 2-(3-Phenoxyphenyl)acetonitrile, molecular formula is C14H11NO, 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 1 284 g of 3-phenoxy benzyl cyanide and 220 g of di-ethyl oxalate were mixed and 400 ml of absolute ethanol was added. To this mixture was added gradually a solution of sodium ethoxide (prepared by dissolving 31 g of sodium in 410 ml of absolute ethanol). After the addition of the ethanol solution the mixture was warmed to 50 C for 30 minutes and then allowed to stand at room temperature for 12 hours. The reaction mixture was then acidified with ice-cooled 10% sulphuric acid (prepared by adding 37 ml of concentrated sulphuric acid to sufficient ice to give 370 ml of ice-cooled diluted acid). The product was extracted with methylene dichloride and the methylene dichloride solution was then washed neutral with distilled water. The product was dried over anhydrous sodium sulphate and the solvent removed. This product was treated with cold hexane to give ethyl 3-cyano-3-(3-phenoxyphenyl)-2-ketopropionate, melting point: 105-109, 90%. The structure was confirmed with proton magnetic resonance analysis (purity > 95%). The preparation of the cyanide from the bromide is illustrated in the following example.

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-Phenoxyphenyl)acetonitrile, its application will become more common.

Reference:
Patent; Shell Oil Company; US4010190; (1977); A;,
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Related Products of 42872-83-3,Some common heterocyclic compound, 42872-83-3, name is 2-Bromo-5-methylbenzonitrile, molecular formula is C8H6BrN, 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.

MethyI-2-(pyrimidin-2-yl)benzonitrile (2); To a 500 mL three neck round bottom flask, equipped with an overhead stirrer, thermocouple and nitrogen inlet and dropped funnel, was charged 2-bromo-5-methylbenzylnitrile1 (20.00 g) and THF (60 mL, 3 V) and was cooled to -15 C. 1.3 M of i-PrMgCI’LiCl (1 10.0 mL, 1.4 equiv) was slowly added at -15 to -12 C. The reaction mixture was stirred at -15 to -12 C for 3.5 h (> 99 A% conversion). 15.45 g of anhydrous ZnCl2 (1.1 equiv, powder) was added to the Grignard reagent at -12 C in one portion. The reaction was exothermic raising the temperature of the reaction mixture to 0 C. The reaction mixture was stirred at -3 to 2 C for 0.5 h and slowly warmed to rt over 0.5 h. The reaction mixture became a homogenous solution and then 2-chloropyrimidine (15.37 g) was added.To a slurry of 1 mol% Pd(OAc)2 (0.229 g), 4 mol% («-Bu)3P (0.826 g or 1.02 mL) in THF (8 mL) was added 2.0 M of BuMgCl (1.02 mL) THF solution to become yellow cloudy solution, The resulting catalyst solution was added to the reaction mixture. The resulting mixture was heated at 55 C for 17 h: (98 A% conversion). The reaction mixture was solvent-switched to isopropyl alcohol (140 mL, total volume) at 40-45 C. Then 5 wt% NH4C1 aqueous solution (70 mL) was added dropwise at 15 to 20 C. The resulting slurry was aged at 10 C for 5 h. The crystalline solid was collected by filtration, rinsed with cold isopropyl alcohol/water (1 : 1, 35 mL), and ^-heptane (30 mL), dried under vacuum with nitrogen sweep and gave desired product2 (17.33 g, 87% isolated yield, 99.5 LCAP purity).HPLC MethodColumn: Zorbax Eclipse Plus CI 8 50 x 4.6 mm, 1.8 muetaiota particle size, Column Temp.: 25 C; Flow Rate: 1.5 mL/min; Detection: 230 nm; Mobile Phase: A: Water 0.1% H3PO4, B: AcetonitrileMobile Phase Program: Time A0 90%5 min 5%6 min 5%6.1 min 90%8 min 90%Compound 2: 3.19 min

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

Reference:
Patent; MERCK SHARP & DOHME CORP.; FENG, Yun Shao; MOSES, Anthony; ZHONG, Yong-Li; WO2012/58129; (2012); A1;,
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Application of 59997-51-2,Some common heterocyclic compound, 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, molecular formula is C7H11NO, 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.

4,4-Dimethyl-3-oxopentanenitrile (80 mmol, 10 g)At room temperature EtOH (200 mL)And stirred at 0 C, hydrazine monohydrate(160 mmol, 7.74 ml) was slowly added. Heated to 90 C and refluxed for 3 hours. After the reaction was completed, the reaction mixture was cooled at room temperature, and the solvent was removed under reduced pressure. Diluted with water, extracted with EtOAc Respectively. Sodium sulfate was added to the extracted organic solvent to remove residual water, and the resultant was separated by MPLC to obtain a red solid Was prepared in a yield of 57%.

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

Reference:
Patent; Korea Research Institute of Chemical Technology; Lee, Kwang Ho; Choe, Gil Don; Park, Sang Jun; Lee, Na Li; Jung, Myung Eun; Kim, Sung Jin; Yang, Kyung Min; Lee, Ji Hee; (28 pag.)KR101726648; (2017); B1;,
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Reference of 215800-25-2,Some common heterocyclic compound, 215800-25-2, name is 2-(4-Bromo-3-methylphenyl)acetonitrile, molecular formula is C9H8BrN, 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 d intermediate 472-(4-bromo-3-methylphenyl)-2-methylpropanenitrileTo a stirred solution of 2-(4-bromo-3-methylphenyl)acetonitrile (11.2 g, 53.3 mmol) in anhydrous DMF (125 mL) is added methyl iodide (13.2 mL, 213 mmol). The solution is cooled to O0C and sodium hydride (60% susp. in oil, 3.84 g, 160 mmol) is added in small portions over 20 min. The reaction mixture is then left stirring and slowly warmed up to room temperature for 18 h. At O0C, water (500 mL) is then slowly added then extracted with ethyl acetate containing 10% of hexanes. The organic layer is separated, dried with MgSO4, filtered and concentrated under reduced pressure to provide the expected product 2-(4-bromo-3-methylphenyl)-2- methylpropanenitrile (12.6 g, 99 %) as a clear yellow oil which is used in the next step without further purification. IH NMR (400 MHz, CHLOROFORM-D) 5 ppm 1.71 (s, 6 H) 2.43 (s, 3 H) 7.14 (dd, /=8.40, 2.34 Hz, 1 H) 7.34 (d, /=2.54 Hz, 1 H) 7.53 (d, /=8.40 Hz, 1 H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromo-3-methylphenyl)acetonitrile, its application will become more common.

Reference:
Patent; ASTRAZENECA AB; WO2008/18827; (2008); A1;,
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Adding a certain compound to certain chemical reactions, such as: 13531-48-1, name is Methyl 3-cyanobenzoate, 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 13531-48-1, Quality Control of Methyl 3-cyanobenzoate

A solution of 2 g (0.01 mol) of methyl-3-cyanobenzoate in 32 ml of THF and 8 ml of water was charged with 2.3 g (0.012 mol) of diethyl dithiophosphate and heated at 80 C. for 24 h. THF was removed and the residue was taken in ethyl acetate. The extract was washed with water and concentrated to afford methyl 3-carbamothioylbenzoate (2.0 g) as a pale yellow solid.

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; Carter, Percy H.; Cherney, Robert J.; Batt, Douglas G.; Duncia, John V.; Gardner, Daniel S.; Ko, Soo S.; Srivastava, Anurag S.; Yang, Michael G.; US2005/54627; (2005); A1;,
Nitrile – Wikipedia,
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