Month: March 2021

Reference of 22364-68-7,Some common heterocyclic compound, 22364-68-7, name is 2-(o-Tolyl)acetonitrile, molecular formula is C9H9N, 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: Benzonitrile (103 mg, 1 mmol) and sodium azide (97.5 mg, 1.5 mmol) were dissolved in 2 ml of dry DMF in a 25 ml round bottom flask. PbCl2 (27.8 mg, 0.1 mmol, 10 mol %) was added to the reaction mixture and stirred at 120 C for 8 h under nitrogen. After completion of the reaction (as monitored by TLC), the reaction mixture was cooled to room temperature and 10 ml of ice water was added followed by addition of 3 N HCl until the reaction mixture became strongly acidic (pH 2-3). The reaction mixture was extracted three times with 20 ml ethyl acetate. The organic layer was washed with brine solution and dried over anhydrous sodium sulfate, and was evaporated under reduced pressure to give a white solid product of 5-phenyl 1H-tetrazole with 81% yield.

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

Reference:
Article; Kant, Rama; Singh, Vishal; Agarwal, Alka; Comptes Rendus Chimie; vol. 19; 3; (2016); p. 305 – 312;,
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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. 887267-38-1, name is 3-Chloro-2,4-difluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 3-Chloro-2,4-difluorobenzonitrile

t-Butyl, methyl malonate (7.5 g, 43 mmol) in DMF (50 mL) was cooled in an ice bath before NaH (60% in mineral oil, 1.0 g, 42 mmol) was added portionwise over 5 minutes with hydrogen evolution. The suspension was allowed to warm to RT for 30 minutes at which time everything was in solution. 3-Chloro-2,4-difluorobenzonit?le (5.0 g, 28.8 mmol) was added as a solid and the reaction was heated to 90 0C for 4 hours and then at RT for 12 hours. TLC (15% ethyl acetate/hexanes) indicated still some starting material but mostly product at a slightly lower Rf. The reaction was diluted with ether and quenched into water containing 2N HCl. The mixture was extracted twice with ether and the ether layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude product was taken up in 1 : 1 methanol :dichloromethane (50 mL) and 2M trimethylsilyldiazomethane in ether was added until the yellow color persisted to re-esterify any acid. The excess diazomethane was quenched with acetic acid and the mixture was reconcentrated. The product mixture was separated by flash chromatogrphy (5-10% ethyl acetate/hexanes, then 10-20%) to afford first some recovered starting material, then a mixture of product and isomeric t-butyl, methyl (R,S)-2-(2-chloro-6- cyano-3-fluorophenyl)malonate by NMR (900 mg), followed by clean title product isomer. 1H-NMR (400 MHz, CDCl3) delta ppm 1.46(s, 9H), 3.79 (s, 3H)5 5.15 (s, IH), 7.448 (d, J = 8.3 Hz, IH), 7.56 (dd, J = 6.0, 8.2, IH).

According to the analysis of related databases, 887267-38-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP &; DOHME CORP.; PASTERNAK, Alexander; SHAHRIPOUR, Aurash; TANG, Haifeng; TEUMELSAN, Nardos, H.; YANG, Lihu; ZHU, Yuping; WALSH, Shawn, P.; WO2010/129379; (2010); A1;,
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Application of 118431-88-2, 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. 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile, This compound has unique chemical properties. The synthetic route is as follows.

The compounds listed below may be prepared in manner similar to the method described above. COMPOUND 612: 1-[4-chloro-2-(methylsulphonyl)phenyl]-2-cyano-3-cyclopropylpropan-1,3-dione, m.p. 116 C., starting from 3-cyclopropyl-3-oxopropanonitrile and 4-chloro-2-(methylsulphonyl)-benzoyl chloride.

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

Reference:
Patent; Rhone-Poulenc Agriculture Limited; US5804532; (1998); A;,
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Adding a certain compound to certain chemical reactions, such as: 90389-96-1, name is 3-((Methylamino)methyl)benzonitrile, 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 90389-96-1, Computed Properties of C9H10N2

To a stirred mixture of 3-[(methylamino)methyl]benzonitrile (6.1 g, 41.7 mmol) and sodium bicarbonate (7.0 g, 83.4 mmol) in ACN (70 mL) was added dropwise tert-butyl 3-bromo- propanoate (7 mL, 41.7 mol). After being stirred at RT for 12 hours, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica, pet ether/EtOAc) to afford the title compound as a pale yellow liquid. 1H NMR (DMSOd6, 400 MHz) delta 7.70 (s, 2H), 7.60 (m, 1 H), 7.51 (m, 1 H), 3.49 (s, 2H), 2.58 (m, 2H), 2.36 (m, 2H), 2.09 (s, 3H), 1.38 (s, 9H).

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-((Methylamino)methyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SERONO S.A.; QUATTROPANI, Anna; MONTAGNE, Cyril; SAUER, Wolfgang; CROSIGNANI, Stefano; BOMBRUN, Agnes; WO2010/112461; (2010); A1;,
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Electric Literature of 499983-13-0,Some common heterocyclic compound, 499983-13-0, name is 4-Bromo-3-fluorophenylacetonitrile, molecular formula is C8H5BrFN, 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 3Preparation of 4-bromo-3-fluorophenylcyclopropanenitrile (V)A solution of 4-bromo-3-fluorophenylacetonitrile (1 g, 4.6 mmoles) in toluene (4 ml) is mixed with 0.6 ml (7 mmoles) of 1,2-dibromoethane, a 50% NaOH aqueous solution (4 ml), and tetrabutylammonium bromide (0.32 g, 1 mmoles). The mixture is kept under stirring at room temperature for 4 hours, then diluted with water and extracted with ethyl acetate. The organic phase is recovered, and the solvent is eliminated under vacuum to give a brown solid, which is subjected to silica gel chromatography purification, to afford an orange to yellow product in the solid form (1 g, yield 90%).

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

Reference:
Patent; Chiesi Farmaceutici S.p.A.; US2011/39934; (2011); A1;,
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Reference of 939-79-7, 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. 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

4-methyl-3- nitrobenzonitrile (Compound 11, manufactured by Tokyo Chemical Industry Co., Ltd.) (965.0 mg, 5.95 mmol) Was dissolved in carbon tetrachloride (10 mL), N-bromosuccinimide (1.270 g, 7.14 mmol) and azobisisobutyronitrile (390.8 mg, 2.38 mmol) were added, and under argon gas atmosphere, 2 And heated under reflux for days. After completion of the reaction, the reaction solution was cooled, water was added, and the mixture was extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (eluent: n-hexane / ethyl acetate = 8/1) to obtain Compound 12 (724 mg, 2.99 mmol, yield 50%).

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

Reference:
Patent; NIHON MEDI-PHYSICS COMPANY LIMITED; KYOTO UNIVERSITY; IZAWA, AKIHIRO; OKUMURA, YUKI; KOBASHI, NOBUYA; ABE, TSUTOMU; SAJI, HIDEO; KIMURA, HIROYUKI; (34 pag.)JP2015/93832; (2015); A;,
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Related Products of 69395-13-7, These common heterocyclic compound, 69395-13-7, name is 4-(2-Hydroxyethyl)benzonitrile, 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 1-(2-(4-Cyanophenyl)ethyl)methane sulphonate Methane sulphonyl chloride (0.856 g, 7.47 mmol) was added to a solution of 2-(4-cyanophenyl)ethanol (1.0 g, 6.80 mmol) and triethylamine (1.03 g, 10.18 mmol), in CH2 Cl2 (30 ml), at +5 C. The mixture was warmed to room temperature and stirred for 2 h before adding H2 O (15 ml), basifying with solid K2 CO3 and extracting with CH2 Cl2 (*3). The combined extracts were dried (Na2 SO4) and evaporated to afford the title-mesylate (1.52 g, 100%), delta (360 MHz, d6 -DMSO) 3.10 (2H, t, J=6.5Hz, CH2 -OMs), 3.12 (3H, s, OMs), 4.46 (2H, t, J=6.5Hz, CH2), 7.52 (2H, d, J=8.2Hz, Ar-H), 7.80 (2H, d, J=8.2Hz, Ar-H).

The synthetic route of 69395-13-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Sharp & Dohme Ltd.; US5807857; (1998); A;,
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Synthetic Route of 60758-86-3,Some common heterocyclic compound, 60758-86-3, name is 3-Ethoxy-4-methoxybenzonitrile, molecular formula is C10H11NO2, 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.

The reaction flask was charged with 400 mL of tetrahydrofuran and 62.5 g (0.8 mol) of dimethylsulfoxide,Stirring to cool to 0 C to 5 C,500 mL (0.8 mol) of a 1.6 M n-butyllithium n-hexane solution having the same temperature of 0 C. to 5 C. was added, and the mixture was stirred for 1.5 hours.Another 179.0 g (0.55 mol) of tributyltin chloride in 450 mL of tetrahydrofuran was added And 88.6 g (0.5 mol) of 3-ethoxy-4-methoxybenzonitrile (Formula III),Stirred for 0.5 hours, naturally warmed to 15 C to 20 C for 2 hours,1000mL purified water was added and the reaction was continued at 15 C to 20 C for 12 hours.The reaction was stopped, the solid obtained in the reaction solution was filtered, and the filter cake was washed with 100 mL each of purified water, n-hexane and tetrahydrofuran in that order. After drying to give a white solid 109.6g, calculated according to the molar yield of Compound III 85.2%, HPLC The degree is 98.1% and the ee is 97.3%.

The synthetic route of 60758-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Peking University Fangzheng Group Co., Ltd.; Chongqing Southwest Synthetic Pharmaceutical Co., Ltd.; Peking University Medical Treatment Industrial Group Co., Ltd.; Fu Biao; Zou Aifang; Luo Li; (9 pag.)CN106866475; (2017); A;,
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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. 3215-64-3, name is 2-(2,6-Dichlorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Product Details of 3215-64-3

EXAMPLE 10 2,7-Diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine (Prepared by the method of U.S. Pat. No. 3,534,039). To a solution of sodium 2-ethoxyethoxide prepared from 0.14 g of sodium and 60 mL of 2-ethoxyethanol was added 2.07 g of 2,4-diamino-5-pyrimidinecarboxaldehyde, and 2.79 g of 2,6-dichlorophenylacetonitrile. The mixture was heated at reflux for 4 hours, allowed to cool to room temperature, and the precipitated product was filtered and washed with diethyl ether to give 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]-pyrimidine, mp 325-332 C.

The synthetic route of 3215-64-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Warner-Lambert Company; US5620981; (1997); A;,
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These common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, 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. Recommanded Product: Diphenyl N-cyanocarbonimidate

A solution of 4-aminopidine (0.612 g, 6.5 mmol), diphenyl N-cyanocarbonimidate (1.540 g, 6.5 mmol) and triethylamine (1.0 mL, 6.5 mmol) in acetonitrile (15 mL) was stirred at 80 C for 2h and illowed to stir at room temperature for 12 h. The reactionmixture was concentrated under reduced pressure to give a residue. The residue was diluted with ethyl acetate, washed with water. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography on silica gel (methanoll dichloromethane = 10/90) to give titled compound (0.700 g, 47 %) as green thickmass.LCMS: mlz 239.10 [M+H] .

The synthetic route of Diphenyl N-cyanocarbonimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak; PANIGRAHI, Sunil Kumar; WO2014/111871; (2014); A1;,
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