Month: March 2021

Electric Literature of 51762-67-5, 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. 51762-67-5 name is 3-Nitrophthalonitrile, 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.

With 3-hydroxybenzoic acid (15mmol) and 3-nitro-phthalonitrile (15mmol) as reactants, the solvent is anhydrous DMSO (30ml), potassium carbonate (45mmol) under nitrogen and the presence, stirred at room temperature The reaction 30 hours, by thin layer chromatography to monitor the end of reaction.The reaction mixture was diluted with sand core funnel filtration, the filtrate was collected, and the filtrate was added to 500ml of ice water mixture, adjusted with 1M hydrochloric acid solution until the solution was acidic precipitation heavy precipitate, was allowed to stand, an organic microporous membrane, repeated washing more times until the solution was neutral, the solid was collected and lyophilized to give a white solid, further use DMF- water purified by recrystallization to give a white desired product, a yield of about 78%.

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

Reference:
Patent; Fuzhou University; Huang, Bindong; Chen, Xingwei; Zheng, Qiaofeng; Ke, Meirong; (19 pag.)CN105622682; (2016); A;,
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Electric Literature of 103146-25-4, A common heterocyclic compound, 103146-25-4, name is 4-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile, molecular formula is C20H23FN2O2, 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.

Experiment 36; Experiment 11 was repeated except that a mixture of 1-propanol and ethylacetate (31:69) was used as the solvent in stead of 1-propanol in a total volume of 4.5 V whereupon extra 2 V 1-propanol was added, 0.25 eq of (+)-O,O’-di-p-toluoyl-(S,S)-tartaric acid was used, and the holding time before filtration was 0.5 h.Molar yield: 28.6%, enantiomeric purity: 98.4% S.

The synthetic route of 103146-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; H. Lundbeck A/S; US2009/69582; (2009); A1;,
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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, Formula: C7H5FN2

NaOMe(25%wtinMeOH,325muL,1.42mmol,1.1eq.)wasaddedtoasolutionof2-amino-6-fluorobenzonitrile (176 mg, 1.29 mmol, 1.0 eq.) in DMF (1.00 mL) at roomtemperature, and stirred for 18 hours. The solution was concentrated in vacuo and theresidue stirred with H2O (10 mL) to give a beige precipitate. This was filtered underreducedpressure,theresiduedissolvedinEtOAcandconcentratedinvacuo,tituratedwithhexanes before remaining solvent was removed in vacuo giving 2-amino-6-methoxybenzonitrile(158mg,1.07mmol,83%)asabeigeamorphoussolid;mp143-145C,lit.136-140C.13

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

Reference:
Article; Sutherell, Charlotte L.; Ley, Steven V.; Synthesis; vol. 49; 1; (2017); p. 135 – 144;,
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Application of 105942-08-3, 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. 105942-08-3 name is 4-Bromo-2-fluorobenzonitrile, 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.

Step 1: Preparation of the starting material: 4-bromo-2-methoxy-benzonitrile. A mixture of 4-bromo-2-fluoro-benzonitrile (15.0 g, 75.0 mmol), methanol (30.4 mL, 350 mmol) and potassium carbonate (31. Ig, 225 mmol) in DMF (150 mL) was stirred under argon at 55 0C overnight. At this point TLC (100percent methylene chloride) revealed no starting material, and the reaction mixture was poured into ether (300 mL) and water (150 mL). The layers were separated, and the organic layer was washed with water (150 mL) and brine (50 mL), dried over Mg2SO4, filtrated, and concentrated under reduced pressure, providing (15.2 g, 95.5percent) of 4-bromo-2- methoxy-benzonitrile as a white solid. 1H-NMR (CDCl3) 7.41 (d, J = 8.1 Hz, IH), 7.16 (dd, J = 8.1, 1,6 Hz, IH), 7.13 (d, J = 1,6 Hz, IH), 3.93 (s, 3H); MS GC-MS (M+ = 211; RT= 6.15 min).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-fluorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; BAYER HEALTHCARE AG; WO2008/25509; (2008); A1;,
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Electric Literature of 76469-88-0,Some common heterocyclic compound, 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, 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.

Methyl 4-(cyanomethyl)benzoate (25g, 0.14mol) dissolved in 300mL methanol was add 160mL 1N NaOH and refluxed for3 hours. Most of the solvent was removed in vacuo. The residue was added 500mL water and acidified to pH 2-3 with concentrated HCl. The generated solid was filtered, washed with water and dried to give the title compound as white solid (21.2g, 92.2%): 1H NMR (400MHz, DMSO-d6) delta 12.89 (brs, 1H), 7.87 (d, J=8.2Hz, 2H), 7.37 (d, J=8.2Hz, 2H), 3.45 (s, 2H); MS(EI): 161[M]+.

The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Danqi; Shen, Aijun; Li, Jian; Shi, Feng; Chen, Wuyan; Ren, Jing; Liu, Hongchun; Xu, Yechun; Wang, Xin; Yang, Xinying; Sun, Yiming; Yang, Min; He, Jianhua; Wang, Yueqin; Zhang, Liping; Huang, Min; Geng, Meiyu; Xiong, Bing; Shen, Jingkang; European Journal of Medicinal Chemistry; vol. 87; (2014); p. 765 – 781;,
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Application of 1187-42-4, 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. 1187-42-4, name is Diaminomaleonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a mixture of 2,3-diaminomaleonitrile (1 mmol) and corresponding aromatic aldehyde (1 mmol) in H2O (5 mL), cerium (IV) ammonium nitrate (5 molpercent) was added and the reaction mixture stirred at room temperature for the desired time, as shown in Table 3. After completion of the reaction (reaction progress was monitored by TLC, ethyl acetate/n-hexane, 3:1), cold water (5?10 mL) was addedand the solid was filtered and washed with cold water/ethanol and air-dried to give the Schiff base product.

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

Reference:
Article; Kalhor, Mehdi; Seyedzade, Zahra; Research on Chemical Intermediates; vol. 43; 5; (2017); p. 3349 – 3360;,
Nitrile – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, 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 127946-77-4, name: 1-Amino-1-cyclopropanecarbonitrile hydrochloride

To a two-necked flask was added 1-((tert-butoxycarbonyl) amino) cyclohexanecarboxylic acid (301 mg, 1.24 mmol)1-amino-1-cyclopropyl cyanide hydrochloride (294 mg, 2.48 mmol) HATU (471 mg, 1.24 mmol) and DMF (6 mL), nitrogen protection, at 0C, triethylamine (0.52 mL, 3.72 mmol) was added, the reaction was stirred at 0C for 4 hours. Water (50 mL) was added to the reaction system, extracted with ethyl acetate (50 mL x2) combined organic phase, the organic phase was washed with saturated brine (50 mL x 2) dried over anhydrous sodium sulfate. Filtration, evaporation of the solvent under reduced pressure, the crude product was purified by silica gel column chromatography (petroleum ether / ethyl acetate (V / V) = 8/1), the title compound was obtained as a white solid (0.34 g, 90%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Amino-1-cyclopropanecarbonitrile hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Dongguan Dongyangguang Pharmaceutical Research And Development Co., Ltd.; Zhou Pingjian; Wang Xiaojun; Yang Chuanwen; Lin Jihua; Cao Shengtian; Yang Xinye; Zhang Yingjun; (33 pag.)CN106928113; (2017); A;,
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Reference of 76469-88-0, 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. 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 1 : A solution of A/fA/-diisopropylethytamine (2.4 mL, 17.1 mmol, 1 eq) in THF (10 mL) was cooled to -78C. A solution of /7-butyllithium in hexanes (2.5M, 6.85 mL, 17.1 eq) was added dropwise with stirring. The solution was warmed to 0C for 10 min, then cooled again to -78C. At -78C, a solution of methyl 4-(cyanomethyl)benzoate (3g, 20 mmol, 1 eq) in THF (8 mL) was added dropwise to the LDA solution (a dark red slurry formed). After stirring the resulting slurry for 10 minutes at -78C, 1-bromo-3,3- dimethylbutane (2.46 mL, 17.9 mmol, 1.05 eq) was added rapidly. The reaction was stirred for 30 minutes at -78C then was warmed to room temperature. After 1h, hexamethylphosphoramide (2.5 mL, 14 mmol) was added, and the reaction was stirred at room temperature for 16h. The reaction mixture was partitioned between EtOAc and 1N HCi. The aqueous layer was discarded, and the organic layer was washed with 1 HCI and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to afford a crude residue which waschromatographed on silica gel (gradient elution, 0% to 30% EtOAc in hexanes, SiO2) to afford the desired product as a white crystalline solid (2.49g, 54%),

The synthetic route of Methyl 4-(cyanomethyl)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SCHERING CORPORATION; WONG, Michael, K.; LAVEY, Brian, J.; YU, Wensheng; KOZLOWSKI, Josheph, A.; DEMONG, Duane, E.; DAI, Xing; STAMFORD, Andrew, W.; MILLER, Michael, W.; ZHOU, Guowei; YANG, De-Yi; GREENLEE, William, J.; WO2011/119559; (2011); 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. 425702-28-9, name is 4,5-Difluoro-2-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 4,5-Difluoro-2-methoxybenzonitrile

Step A: di-fert-Butyl (4-cvano-2-fluoro-5-methoxyphenyl)propanedioate A suspension of NaH (60% in mineral oil, 0.33 g, 8.3 mmol) in dry DMF (20 mL) was stirred and cooled to 0 C, and di-tert-butyl malonate (1.5 g, 7.1 mmol) was added. The mixture was allowed to warm to room temperature before addition of 4, 5-difluoro-2-methoxybenzonitrile (1.0 g, 5.9 mmol). The mixture was heated at 80 C for 4 h with stirring, then the reaction mixture was cooled to room temperature and poured into a mixture of ice-water (100 mL) and AcOEt (100 mL). The layers were separated, and the organic layer was washed successively with water, and brine, then dried over Na2S04 and concentrated. The residue was purified by flash chromatography (silica gel, EtOAc/hexanes, 0 -> 10%) to give the di-tert-butyl (4-cyano-5- fiuoro-2-methoxyphenyl) propanedioate. LCMS: [(M+l)-t-Bu,C02-t-Bu]+ = 210.

The synthetic route of 425702-28-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; WO2013/39802; (2013); A1;,
Nitrile – Wikipedia,
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Electric Literature of 52133-67-2, A common heterocyclic compound, 52133-67-2, name is Ethyl 2-cyano-4,4-diethoxybutyrate, molecular formula is C11H19NO4, 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.

To a solution of sodium ethoxide (210 mL, 563 mmol; 21 percent in EtOH) in absolute EtOH (290 mL) were added ethyl-2-cyano-4,4-diethoxybutanoate (45 g, 281 mmol) and 2,2- dimethyl-propionamidine (59 g, 256 mmol) and heated to reflux for 12 h. The mixture was concentrated, the residue was diluted with water (100 mL) and acidified (pH 6-7) with aqueous 2N HC1 solution. The precipitate was filtered, dried under vacuum and dissolved in EtOH (100 mL). H2S04 (10 mL) was added at 0 ¡ãC and the mixture was heated to reflux for 2 h. After cooling to 25 ¡ãC the solution was made basic (pH~8-9) with NH3 aq.. The precipitate was filtered and dried under vacuum to yield 2-tert-butyl-l, 7-dihydro-pyrrolo [2,3-d]pyrimidin-4-one (18 g, 47percent) as white solid which was used in the next step without further purification. MS(m/e): 192 (M+H).

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; GRETHER, Uwe; KIMBARA, Atsushi; NETTEKOVEN, Matthias; ROEVER, Stephan; ROGERS-EVANS, Mark; SCHULZ-GASCH, Tanja; WO2014/177527; (2014); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts