Month: September 2021

Electric Literature of 873-74-5, 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. 873-74-5 name is 4-Aminobenzonitrile, 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.

The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is p-cyanoaniline, the reaction time is 12 h, and the other reaction and post-treatment processes are the same as in the embodiment 28. The preparation method of the trifluoromethyl aromatic amine of the present embodiment, the aromatic amine is aniline, and the nickel compound is nickel hydroxide.The base is potassium carbonate, and the reaction process parameters are: 1-trifluoromethyl-1,2-phenyliodo-3(H)-one (0.5 mmol, 1.0 eq).Aromatic amine (1.5 mmol, 3.0 eq), nickel hydroxide 10 mol%, potassium carbonate (1.5 mmol, 3.0 eq),DMSO (2 mL) was reacted at 35 C for 2 h, and the other reactions and workup procedures were the same as in Example 1.

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

Reference:
Patent; Zhengzhou Taijihongnuo Pharmaceutical Co., Ltd.; Wu Yusheng; Gao Xianying; Geng Yang; Han Shuaijun; Liang Apeng; Li Jingya; Zou Dapeng; Wu Yangjie; (19 pag.)CN108503552; (2018); 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. 19179-31-8, name is 3,5-Dimethoxybenzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H9NO2

To a solution of 3,5-dimethoxybenzonitrile (2 g, 12.2 mmol) in dichloromethane (20 was added slowly BBr3 (15 mL, 1 M, 15 mmol) at -50 C under N2. After addition, the mixture was stirred at -50 C for 2 h and stirred at r.t for 20 hr. The mixture was slowly poured into ice-water with stirring and extracted with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column (petroleum ether/ethyl acetate (2: 1) as eluent) to afford 3,5- dihydroxybenzonitrile (1.43 g). 1H NMR (DMSO-d6, 400 MHz): delta 10.02 (s, 2H), 6.56 (d, J= 2.0 Hz, 2H), 6.51 (t, J = 2.0 Hz? 1H).

The synthetic route of 19179-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ARRINGTON, Kenneth, L.; BURGEY, Christopher; GILFILLAN, Robert; HAN, Yongxin; PATEL, Mehul; LI, Chun Sing; LI, Yaozong; LUO, Yunfu; LEI, Zhiyu; XU, Jiayi; WO2014/58747; (2014); A1;,
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Related Products of 115279-73-7, A common heterocyclic compound, 115279-73-7, name is 1-(4-Aminophenyl)cyclopentanecarbonitrile, molecular formula is C12H14N2, 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 500 ml four-necked flask equipped with a stirrer, a thermometer and a distillation system, 100 g of toluene and 11.2 g (0.06 mol) of 1-(4-aminophenyl)cyclopentylcarbonitrile (V) were added. 0.25 g of 4-dimethylaminopyridine, maintaining an internal temperature of 95-105 C. A solution of 12.9 g (0.05 mol) of ethyl 2-[(pyridin-4-ylmethyl)amino]-3-pyridinecarboxylate (IV2) prepared in Example 4 and 30 g of toluene was added dropwise, and the mixture was dropped over 2 hours. Thereafter, the reaction was stirred at 110-115 C for 5 hours, and the formed ethanol was distilled off. After the reaction was completed, the temperature was lowered to 20-25 C, filtered, and the filter cake was washed with 20 g of toluene, the filtrate was combined, and toluene was distilled off under reduced pressure. The tert-butyl ether was recrystallized, filtered and dried to give 18.1 g of a white solid powder of eptatinib (I), yield 91.2%, liquid phase purity 99.92%, melting point 158.5-160.0 C.

The synthetic route of 115279-73-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Cui Qingrong; Liu Yuesheng; Qu Hu; Lv Qiangsan; Ju Lizhu; (10 pag.)CN109020881; (2018); A;,
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Adding a certain compound to certain chemical reactions, such as: 78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, 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 78473-00-4, Recommanded Product: 78473-00-4

Into a 1000 mL three-neck flask were put 9.4 g (50 mmol) of 4-amino-3,5-dichlorobenzonitrile, 26 g (253 mmol) of isobutylboronic acid, 54 g (253 mmol) of tripotassium phosphate, 2.0 g (4.8 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-phos), and 500 mL of toluene. The air in the flask was replaced with nitrogen, and this mixture was degassed while being stirred under reduced pressure. After the degassing, 0.88 g (0.96 mmol) of tris(dibenzylideneacetone)palladium(0) was added, and the mixture was stirred at 130 C. under a nitrogen stream for 8 hours to be reacted. Toluene was added to the reacted solution, and the solution was filtered through a filter aid in which Celite, aluminum oxide, and Celite were stacked in this order. The obtained filtrate was concentrated to give an oily substance. The obtained oily substance was purified by silica gel column chromatography. Toluene was used as a developing solvent. The resulting fraction was concentrated to give 10 g of a yellow oily substance in a yield of 87%. The obtained yellow oily substance was identified as 4-amino-3,5-diisobutylbenzonitrile by nuclear magnetic resonance (NMR) spectroscopy.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Amino-3,5-dichlorobenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Semiconductor Energy Laboratory Co., Ltd.; Seo, Satoshi; WATABE, Takeyoshi; MITSUMORI, Satomi; (178 pag.)US2017/92890; (2017); A1;,
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Related Products of 16932-49-3, These common heterocyclic compound, 16932-49-3, name is 2,6-Dimethoxybenzonitrile, 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.

Example 1 Synthesis of 2,6-Dihydroxybenzonitrile (2-Cyanoresorcinol) One potential method utilizes boron tribromide to demethylate 2,6-dimethoxybenzonitrile (1 in ) to generate 2,6-dihydroxybenzonitrile (2). Into a 250 mL 3-neck round bottom flask equipped with stir bar, nitrogen inlet, thermometer, and addition funnel was charged 2,6-dimethoxybenzonitrile (3.99 g, 24.5 mmol) and methylene chloride (27 mL). The solution was cooled to -78 C. by submerging the flask in a dry ice/acetone bath. A solution of boron tribromide (25 g, 99.8 mmol) in methylene chloride (27 mL) was added dropwise via the addition funnel over a period of 1 hour. The temperature was maintained at -78 C. for 2 hours. The mixture was allowed to rise to room temperature. The reaction was then stirred at room temperature overnight and refluxed at 55 C. for 10 hours. Excess boron tribromide was decomposed carefully by the addition of moist methylene chloride. Upon removal of the solvent, the crude product was passed through a column of silica gel using 5% acetone in methylene chloride as eluent to afford 1.42 g (43.0%) of a light brown solid, m.p. 197.5-199.6 C. 1H-NMR (DMSO-d6): 6.39-6.41 (d, 2H, Ar-H), 7.20-7.24 (t, 1H), 10.78 (s, 2H, Ar-O-H).

The synthetic route of 16932-49-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The United States of America, as represented by the Secretary of the Air Force; Tan, Loon-Seng; Wang, David Huabin; US9139696; (2015); B1;,
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Related Products of 6575-12-8,Some common heterocyclic compound, 6575-12-8, name is 2,6-Dibromobenzonitrile, molecular formula is C7H3Br2N, 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.

42b) 2-(2,6-Dibromophenyl)-3-{[4-(1,1-dimethylethyl)phenyl]methyl}-6-hydroxy-4(3H)-pyrimidinone; A 1 M solution of dimethylaluminium chloride in hexane (2.20 mL, 2.20 mmol) was added to a stirred mixture of 4-tert-butylbenzylamine (0.326 g, 2.00 mmol), 2,6-dibromobenzonitrile (0.587 g, 2.25 mmol) and toluene (6 mL) at room temperature. The mixture was stirred in a microwave reactor at 160 C. for 0.5 h, then cooled and the solvent removed under reduced pressure. Diethyl malonate (1.28 g, 8.00 mmol), 2-methoxyethanol (12 mL) and 4.37 M sodium methoxide in methanol (1.83 mL, 8.00 mmol) were added and the mixture refluxed under nitrogen for 18 h. After cooling, the mixture was poured into water (150 mL), washed with ether, acidified to pH 1 with 6 M aqueous hydrochloric acid, and extracted with ethyl acetate. The extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with ether and the solid collected, washed with ether and dried to give the title compound (0.361 g, 37%) as a cream solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 1.23 (s, 9 H) 4.86 (s, 2 H) 5.59 (s, 1 H) 6.74-6.80 (m, 2 H) 7.17-7.22 (m, 2 H) 7.43 (t, J=8.08 Hz, 1 H) 7.76 (d, J=8.08 Hz, 2 H) 11.86 (s, 1 H).

The synthetic route of 6575-12-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
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Application of 16588-02-6, 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. 16588-02-6, name is 2-Chloro-5-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 17 2-(3,4,5-Trichlorophenoxy)-5-nitrobenzonitrile In a 250 ml single-neck flask equipped with a magnetic stirrer and a reflux condenser fitted with a nitrogen bubbler were placed 8.68 g (0.0475 moles) of 2-chloro-5-nitrobenzonitrile 9.67 g (0.0489 moles) of 3,4,5-trichlorophenol, 6.75 g (0.0489 moles) of anhydrous K2 CO3, and 75 ml of acetonitrile. The mixture was heated to reflux and held there for 3 hrs. The reaction mixture was cooled to room temperature and diluted with 150 ml of water. The product separated as a solid. The solid was filtered off, washed thoroughly with water, and air-dried. The air-dried solid was recrystallized from a mixture of 200 ml of absolute ethanol and 100 ml of acetone to give 11.62 g (71% yield) of purified 2-(3,4,5-trichlorophenoxy)-5-nitrobenzonitrile as small white crystals, mp 162-164 C.

The synthetic route of 2-Chloro-5-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Dow Chemical Company; US4332820; (1982); A;,
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Related Products of 33143-29-2,Some common heterocyclic compound, 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, molecular formula is C12H11NO, 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 4 2,2-Dimethyl-3,4-dihydro-3-(t-butoxycarbonyl)amino-6-cyano-2H-1-benzopyran (E4) A solution of 6-cyano-2,2-dimethyl-2H-1-benzopyran (1.0g) and N,N-dichloro-t-butylurethane (1.1g) in toluene (20 ml) was heated at 50oC for 5 h. The solution was cooled, and solvent removed in vacuo . The residue was dissolved in dioxan (20 ml) at 0oC, a solution of ammonium acetate (2.08g) in water (20 ml) added, and zinc dust (1.76g) added portionwise. The mixture was stirred for 18 h at room temperature, decanted, and diluted with water and extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo . The residue was chromatographed on a silica gel column eluted with ethyl acetate:pentane (1:9) to give the title compound as a solid (1.17g, 72%) which recrystallized from 60-80opetrol as needles having m.pt. 141-2oC. 1H n.m.r. (CDCl3) delta 1.32 (s, 3H); 1.38 (s, 3H); 1.45 (s, 9H); 2.70 (dd, J=15, 4, 1H); 3.13 (dd, J=15, 4, 1H); 3.97 (m, 1H); 4.58 (d, J=9, N H); 6.87 (d, J=9, 1H); 7.40 (m, 2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,2-Dimethyl-2H-chromene-6-carbonitrile, its application will become more common.

Reference:
Patent; BEECHAM GROUP PLC; EP375449; (1990); A2;,
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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, name: 2-(2,6-Dichlorophenyl)acetonitrile

1.4 6-(2,6-dichlorophenyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7-amine.; 5.47 g of 60% NaH was added over 5 minutes to 21 g of the aldehyde obtained in the preceding step dissolved in 240 ml of DMF cooled to 5 C., then 29.05 g of 2,6-dichlorophenylacetonitrile was added over 20 minutes. Stirring was continued for 30 minutes at 5 C. then overnight at ambient temperature. The reaction medium was cooled to 5 C. and 65 ml of a saturated solution of NH4Cl was added followed by 500 ml of a water/ice mixture; a red precipitate was formed which was filtered, washed twice with water, completely drained, washed with ether using 100 ml of chloroform, then again with ether; after drying, a beige solid was obtained. MP=250-253 C., m=29.92 g. The ether and chloroform wash phases were concentrated to dryness and taken up in a little chloroform to which ether had been added: a second quantity of 3.15 g was obtained. Total m=33.07 g.

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; Sanofi-aventis; US2007/167469; (2007); A1;,
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Reference of 621-03-4, 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. 621-03-4, name is 2-Cyano-N-phenylacetamide belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Pyridine was added dropwise with stirring to cyanoacetamide 2a-e(15 mmol) in a round-bottom flask until complete dissolution of the cyanoacetamide. DMAP (18 mg, 0.15 mmol) and mercaptoacetic acid (3.2 ml, 46mmol) were added to the obtained solution. The obtained mixture was refluxed for 12 h in a flask equipped with a reflux condenser,then diluted with 0.5 HCl solution (5 ml).The precipitate of 1,3-thiazolidinone 1 was filtered off and washed with hot MeCN (15 ml). When necessary, the product was additionally purified by refluxing a suspension of thiazolidine in MeCN, followed by hot filtration

The synthetic route of 2-Cyano-N-phenylacetamide has been constantly updated, and we look forward to future research findings.

Reference:
Article; Obydennov, Konstantin L.; Galushchinskiy, Aleksei N.; Kosterina, Marya F.; Glukhareva, Tatiana V.; Morzherin, Yuri Yu.; Chemistry of Heterocyclic Compounds; vol. 53; 5; (2017); p. 622 – 625; Khim. Geterotsikl. Soedin.; vol. 53; 5; (2017); p. 622 – 625,4;,
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