Category: nitriles-buliding-blocks

Reference of 60758-87-4, The chemical industry reduces the impact on the environment during synthesis 60758-87-4, name is 3,4-Diethoxybenzonitrile, I believe this compound will play a more active role in future production and life.

Reference Example 3 A solution of 29 g of 3,4-diethoxybenzonitrile and 23 g of thioacetamide in 120 ml of 10% hydrochloric acid-DMF was sirred at 90 C. for 3 hours and then 130 C. for 5 hours. After evaporation of the solvent, the residue was washed with diethyl ether (2*100 ml) and water (2*100 ml). The resulting crystals were collected by filtration and dried to obtain 21.7 g of 3,4-diethoxythiobenzamide.

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

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US6291487; (2001); B1;,
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Synthetic Route of 105-34-0,Some common heterocyclic compound, 105-34-0, name is Methyl 2-cyanoacetate, molecular formula is C4H5NO2, 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: A 10 mL round-bottomed flask was charged with carbonyl compound (1 mmol), active methylene compound (1 mmol), S-4 (12 mg and 20 mol% of the substrates), and water (3 mL). The reaction mixture was stirred at room temperature. The suspension was stirred at room temperature for the lengths of time shown in Table 4. The reaction progress was monitored by thin layer chromatography usingn-hexane-EtOAc (5:1) as eluent. After completing the reaction, the reaction mixture solidified in the round-bottomed flask. The solids were then dissolved in hot ethanol (30 mL). The catalyst was removed by filtration and washed with ethanol. The solid product was obtained after the ethanol was concentrated in vacuo.

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

Reference:
Article; Zhao, Xian-Liang; Yang, Ke-Fang; Zhang, Yan-Ping; Zhu, Ju; Xu, Li-Wen; Chinese Chemical Letters; vol. 25; 8; (2014); p. 1141 – 1144;,
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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. 123-06-8, name is Ethoxymethylenemalononitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethoxymethylenemalononitrile

Triethylamine (9.7mL, 69.6mmol) was added to tert-butylhydrazine hydrochloride (8.67g, 69.6mmol) After adding absolute ethanol (460mL) and stirring at room temperature to dissolve, Ethoxymethylenemalononitrile (8.5 g, 69.6 mmol) was added in small portions, the solution was heated to reflux for 3 hours, and then the solvent was evaporated in vacuo to obtain a crude orange product. It was extracted with a mixed solution of ethyl acetate (0.5 L) and water (0.25 L), dried over anhydrous magnesium sulfate, and the organic layer was evaporated to obtain an orange solid. Continue to wash the obtained solid with a cyclohexane solution containing 10% ethyl acetate to obtain crystalline solid 5-amino-1-tert-butyl 1hydro-pyrazole-4-cyano 9.54g (yield 83% ).

According to the analysis of related databases, 123-06-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sichuan University Huaxi Hospital; Chengdu Huaxi Jingzhun Medical Industrial Technology Institute Co., Ltd.; He Yang; Li Weimin; Zhou Xinglong; Wu Qiong; Wu Xiaoai; Chen Hai; Huang Ridong; Chai Yingying; (17 pag.)CN110642861; (2020); A;,
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Adding a certain compound to certain chemical reactions, such as: 658-99-1, name is 2-(3,4-Difluorophenyl)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 658-99-1, Application In Synthesis of 2-(3,4-Difluorophenyl)acetonitrile

Example A2 erythro- and threo-methyl 4-cyano-4-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)butanoate (Table 2, Examples erythro-Ibb748 and threo-Ibb748) Under protective gas (Ar), 5 ml of N,N-dimethylformamide and 0.067 g (1.244 mmol) of potassium tert-butoxide were added to 1.127 g (6.219 mmol) of methyl 3-(5-fluoropyridin-3-yl)acrylate and 1.000 g (6.530 mmol) of (3,4-difluorophenyl)acetonitrile in 15.0 ml of toluene, and the mixture was stirred at 70 C. for 5 h. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane. The mixture was washed successively with water, 0.1 N aqueous hydrochloric acid and saturated aqueous sodium chloride solution and the organic phase was dried over sodium sulphate. Removal of the solvent under reduced pressure and chromatography of the residue on silica gel gave 1.008 g (46% of theory) of a mixture of erythro- and threo-methyl 4-cyano-4-(3,4-difluorophenyl)-3-(5-fluoropyridin-3-yl)butanoate (erythro-Ibb748:threo-Ibb748=60:40). The configuration was assigned by comparison of the chemical shifts of the respective CHCN doublets at 4.12 ppm and 4.48 ppm, respectively, in the 1H-NMR (CDCl3).

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-(3,4-Difluorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER CROPSCIENCE AG; JAKOBI, Harald; MOSRIN, Marc; DIETRICH, Hansjoerg; GATZWEILER, Elmar; ROSINGER, Christopher Hugh; SCHMUTZLER, Dirk; (66 pag.)US2015/327546; (2015); A1;,
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Some common heterocyclic compound, 4475-95-0, name is 2-Amino-2-methylbutanenitrile, molecular formula is C5H10N2, 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. category: nitriles-buliding-blocks

5.00 g (50.94 mmol) of 2-amino-2-methylbutanonitrile [synthesis described in: Lonza AG, U.S. Pat. No. 5,698,704 (1997); Deng, S. L. et al. Synthesis 2001, 2445; Hjorringgaard, C. U. et al. J. Org. Chem. 2009, 74, 1329; Ogrel, A. et al. Eur. J Org. Chem. 2000, 857] were initially charged in 50 ml of THF and 6.5 ml of water, 21.83 g (157.92 mmol) of potassium carbonate were added and, at 0 C., 7.9 ml (56.04 mmol) of benzyl chlorocarbonate (benzyl chloroformate) were added. After the addition of 8 ml of THF and 3 ml of water, the reaction mixture was stirred overnight, slowly warming to RT. Water was then added, and the mixture was extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was dissolved in diethyl ether and precipitated with petroleum ether. The product was filtered off and the solid was washed with a little petroleum ether and dried under high vacuum. This gave 11.35 g of the target compound (93% of theory, purity 97%). LC-MS (Method 5): Rt=0.97 min MS (ESpos): m/z=233 (M+H)+1H NMR (400 MHz, DMSO-d6): delta=0.95 (t, 3H), 1.51 (s, 3H), 1.75-1.95 (m, 2H), 5.07 (s, 2H), 7.30-7.43 (m, 4H), 7.88-8.03 (m, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4475-95-0, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; VALOT, Gaelle; LINDNER, Niels; FOLLMANN, Markus; STASCH, Johannes-Peter; WUNDER, Frank; MARQUARDT, Tobias; DIETZ, Lisa; LI, Volkhart Min-Jian; (74 pag.)US2017/233345; (2017); A1;,
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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. 6609-57-0, name is 2-Ethoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-Ethoxybenzonitrile

Preparation 7 2-ethoxy-5-(4-ethyl-1-piperazinylsulfonyl)benzonitrile Commercially available 2-ethoxybenzonitrile (25 g, 0.17 Mol) was added dropwise to an ice cooled mixture of chlorosulfonic acid (50.8 mL, 0.765 Mol) and thionyl chloride (12.4 mL, 0.17 Mol) so as to keep the temperature below 10 C. The reaction was then stirred at ambient temperature for 18 h before being poured onto ice/water. This mixture was stirred 1 hr before the precipitated material was filtered off. The resultant solid was dissolved in acetone (300 mL) and triethylamine (25 mL, 0.179 Mol) was added followed by a slow addition of N-ethylpiperazine (25 mL, 0.198 Mol).

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 6609-57-0.

Reference:
Patent; Dunn, Peter James; Dunne, Catherine; US2002/13464; (2002); A1;,
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Adding a certain compound to certain chemical reactions, such as: 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile, 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 16588-02-6, Recommanded Product: 16588-02-6

A mixture of 3 -methyl- IH-1, 2;4-triazole (6.83 g, 82 mmol), 2- chloro-5-mtrobenzomtrile (15 g, 82 mmol), and potassium carbonate (34.1 g, 246 mmol) in anhydrous acetonitrile (200 mL) was heated at 70 0C for 16 h. The dark brown reaction mixture was allowed to cool to rt and was poured into water (500 mL). The aqueous mixture was extracted with EtOAc (3 x 200 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified using silica gel chromatography (40-100% ethyl acetate/hexane, linear gradient) to afford 2-(3-methyl~lH-l,2,4-triazol-l-yl)-5- nitrobenzonitrile (10.9 g, 58 % yield). LC-MS (M+H)+ – 230.1. 1H NMR (500 MHz, chloroform-D) delta ppm 2.53 (s, 3 H) 8.10 (d, J-9.16 Hz, 1 H) 8.56 (dd, J-9.16, 2.44 Hz, 1 H) 8.68 (d, J-2.44 Hz, 1 H) 8.93 (s, 1 H).

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:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MARCIN, Lawrence, R.; THOMPSON, Lorin, A., III; BOY, Kenneth, M.; GUERNON, Jason, M.; HIGGINS, Mendi, A.; SHI, Jianliang; WU, Yong-Jin; ZHANG, Yunhui; MACOR, John, E.; WO2010/83141; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 134997-74-3, name is 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile, 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 134997-74-3, Quality Control of 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile

To a stirred solution of 3-oxo-3,4-dihydro-2H-benzo[b][1 ,4]oxazine-6-carbonitrile (3.30 g, 1 9.0 mmol) in N,N-dimethylformamide (35 mL) was added sodium hydride (758 mg, 1 9 mmol, 60% dispersion in mineral oil) and iodoethane (3.84 g, 25 mmol, 1 .97 mL) at 0 C. The mixture was warmed to 20 00. After 3 h, the mixture was cooled to 0 C, quenched by addition of water (50 mL), and extracted with ethylacetate (60 mL x 4). The combined organic phases were washed with saturated aqueous sodium chloride solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give crude product that was purified by chromatography (silica, petroleum ether : ethyl acetate 50:1 to 5:1) to give 4-ethyl-3-oxo-3,4-dihydro-2H-benzo[b][1 ,4]oxazine-6-carbonitrile (1 .30 g, 6.43 mmol, 34 %) as a white solid. 1H NMR (400 MHz, CDC3) O 7.25 (dd, J 1.8, 8.3 Hz, 1 H), 7.17 (d, J 1 .8 Hz, 1 H), 6.98 (d, J8.3 Hz, 1H), 4.62 (s, 2H), 3.93 (q, J 7.2 Hz, 2H), 1.23 (t, J 7.2 Hz, 3H); LOMS (ESI) m/z 203.1 [M÷H]÷.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile, and friends who are interested can also refer to it.

Reference:
Patent; YUMANITY THERAPEUTICS; LUCAS, Matthew; LE BOURDONNEC, Bertrand; WRONA, Iwona; PANDYA, Bhaumik; TIVITMAHAISOON, Parcharee; OZBOYA, Kerem; VINCENT, Benjamin; TARDIFF, Daniel; PIOTROWSKI, Jeff; SOLIS, Eric; SCANNEVIN, Robert; CHUNG, Chee-Yeun; ARON, Rebecca; RHODES, Kenneth; (489 pag.)WO2018/81167; (2018); A1;,
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Synthetic Route of 64248-63-1, The chemical industry reduces the impact on the environment during synthesis 64248-63-1, name is 3,5-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

3-Fluoro-5-methoxybenzoic Acid In a 250 ml round bottom flask equipped with stir bar added 3,5-Difluorobenzonitrile (4.2 g, 30.4 mmol), sodium methoxide (10.4 ml, 45.6 mmol, 25% methanol) and dimethylformamide (40 ml). Stirred the resulting reaction mixture at room temperature, overnight. The reaction mixture was concentrated in-vacuo and residue was dissolved in dichloromethane (200 ml). The organic phase was washed sequentially with water (150 ml) and brine (150 ml), dried (sodium sulfate) and concentrated in-vacuo. The crude residue was purified on silica gel using 10% diethyl ether in hexanes to isolate 3-Fluoro-5-methoxybenzonitrile (1.63 g) as a white solid.

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, 3,5-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Wagenen, Bradford Van; Stormann, Thomas M.; Moe, Scott T.; Sheehan, Susan M.; McLeod, Donald A.; Smith, Daryl L.; Isaac, Methvin Benjamin; Slassi, Abdelmalik; US2003/55085; (2003); A1;,
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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. 950596-58-4, name is 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile

(f) Erlotinib free base:; To 2-amio-4,5-bis(2-methoxyethoxy)benzonitrile (4.57g, 0.0172moles) was added toluene (30ml), N’-(3-ethynylphenyl) N,N-dimethyl formamidine (3.44g, 0.0172moles) and acetic acid (0.5ml) refluxed the reaction mixture for about 4hrs cooled the reaction mass to room temperature, toluene layer was separated washed with water and chilled toluene layer to yield crude erlotinib and which was further recrystallized from a polar solvent such as methanol to get pure off- white crystalline compound(3g) having mp 149-153 0C.

The synthetic route of 950596-58-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VITTAL MALLYA SCIENTIFIC RESEARCH FOUNDATION; WO2007/138612; (2007); A2;,
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