Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 2032-34-0, name is 3,3-Diethoxypropanenitrile, 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 2032-34-0, Application In Synthesis of 3,3-Diethoxypropanenitrile

General procedure: Method I. A mixture of Py (4.4 ml) and AcOH (3.0 ml) was stirred and treated by the addition of 5-aminoazole1a-h (0.01 mol) and (2E)-(3-morpholin-4-yl)-acrylonitrile (2) (1.38 g, 0.01 mol). The obtained mixture was refluxed at 150C for 5 h. After refluxing, the mixture was cooled. The precipitate that formed was filtered off, washed with a small amount of EtOH, and dried. Method II. A solution (or suspension) of the appropriate aminoazole 1a-h (0.01 mol) in solvent (15 ml) (EtOH in the case of compound 3a, dioxane in the case of compounds 3b-h) was stirred at 50C and treated by adding 3,3-diethoxypropionitrile (4) (1.5 ml, 0.01 mol), then 36% HCl solution (0.86 ml, 0.01 mol). The reaction mixture was refluxed for 2.5-3 h, the suspension (or solution) was cooled to room temperature, and the target product was isolated by the method indicated for each particular compound. [1,2,4]Triazolo[1,5-a]pyrimidin-7-amine (3). Yield1.01 g (75%, method I), beige powder, mp 276-279C (MeCN). Method II. The obtained suspension was neutralized with Et3N, the precipitate was filtered off, washed with EtOH, CHCl3, and air-dried. The dry product was dissolved in 2 (20 ml) and treated by adding a solution of KOH (0.561 g) in 2 (10 ml), then stirred overnight at room temperature. The obtained suspension was neutralized with AcOH to pH ~7 and evaporated to dryness at reduced pressure, the dry residue was triturated with EtOH, filtered, and washed with EtOH. Yield 0.96 g (71%, method II), white powder, mp 276-278C. IR spectrum, nu, cm-1: 3244, 3298 (NH2). 1H NMR spectrum (400 MHz), delta, ppm (J, Hz): 6.30 (1H, d, J = 5.5,H-6); 8.14 (2H, br. s, NH2); 8.26 (1H, d, J = 5.5, H-5); 8.43(1H, s, H-2). 13C NMR spectrum (101 MHz), delta, ppm 90.8 (C-6); 149.3 (C-7); 153.5 (C-5); 154.4 (C-2); 155.9 (C-3a).Found, %: 44.29; H 3.88; N 52.10. C5H5N5. Calculated,%: 44.44; H 3.73; N 51.83.

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

Reference:
Article; Gazizov, Denis A.; Fedotov, Victor V.; Gorbunov, Evgeny B.; Ulomskiy, Evgeny N.; Yeltsov, Oleg S.; Rusinov, Gennady L.; Rusinov, Vladimir L.; Chemistry of Heterocyclic Compounds; vol. 55; 6; (2019); p. 573 – 577; Khim. Geterotsikl. Soedin.; vol. 55; 6; (2019); p. 573 – 577,5;,
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6621-59-6, name is 6-Bromohexanenitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. SDS of cas: 6621-59-6

6-[5-(1-methyl-2-pyrrolidinyl)-2-pyridinyl]hexanenitrile (6). A stirred mixture of 6-aminonicotine (0.62 g, 3.5 mmol) and NaH (80% in mineral oil, 0.16 g, 5.25 mmol) in dry toluene (20 mL) was refluxed for 2 h and then cooled to room temperature. 6-Bromohexane-nitrile (0.65 g, 3.7 mmol) was added and the reaction was left at ambient temperature over night. The solvent was evaporated and the residue was chromatographed [silica gel, CHCl3/MeOH/NH4OH (18:3:0.1)] to afford 0.40 g (41%) of 6; IR (film): 2270 cm-3 (CN); 1H-NMR (CDCl3, 270 MHz) delta 7.95 (d, J=2.5 Hz, 1H), 7.47 (dd, J=2.5, 8.5 Hz, 1H), 6.39 (d, J=8.5 Hz, 1H), 4.49 (m, 1H), 3.36-3.16 (m, 3H), 2.90 (t, J=9 Hz, 1H), 2.36 (t, J=7 Hz, 2H), 2.29-2.19 (m, 1H), 2.19-2.06 (m, 1H), 2.14 (s, 3H), 2.00-1.50 (m, 9H); 13C NMR (CDCl3, 68 MHz) delta 158.2, 147.4, 136.5, 126.4, 119.4, 106.9, 68.5, 56.7, 41.7, 40.0, 34.3, 28.7, 26.0, 25.0, 22.1, 16.7;

The synthetic route of 6621-59-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Independent Pharmaceutica AB; US6656469; (2003); B1;,
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Application of 654-70-6, 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. 654-70-6, name is 4-Cyano-3-trifluoromethylaniline belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a slurry of 4-amino-2- (trifluoromethyl) benzonitrile (30.09 g, 162 mmol) and NaBH3CN (21.35 g, 340 mmol) in CH2CI2 (160 mL) at ice bath temperature was added neat TFA (160 mL, 2.08 mol), dropwise at a rate such that the internal temperature remained below 5C (CAUTION : exothermic reaction with hydrogen gas evolution). TRIFLUOROACETALDEHYDE hydrate (52.2 g, 405 MMOL) was then added over 5 minutes (CAUTION : slightly exothermic reaction, with gas evolution). After 41 h, the mixture was slowly poured into satd NAHC03 (1 L) at 0C. The mixture was then completely neutralized by portionwise addition of solid NAHC03. The mixture was stirred 30 min and precipitated solids were collected by filtration. Organic and aqueous phases of the filtrate were separated, and the aqueous layer extracted with CH2CI2 (3 X 150 mL). Combined organic extracts were concentrated to dryness, combined with the solids collected previously, dissolved in EtOAc, washed (H20, brine), dried over NA2SO4, filtered through a short pad of Celite, and concentrated to dryness. The residue was filtered through a pad of silica gel (EtOAc/hexanes) and concentrated to dryness. Recrystallization from EtOAc/hexanes yielded 32.61 g of the title compound as slightly tan crystalline plates, mp 132. 5-134C :’H NMR (300 MHz, MeOH-d4) 8 7.59 (d, J = 8. 8 Hz, 1 H), 7.05 (d, J = 2.2 Hz, 1 H), 6.92 (dd, J = 8.7, 2.4 Hz, 1 H), 3.92 (q, J = 9.2 Hz, 2H).

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

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/795; (2005); A2;,
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Application of 654-70-6, A common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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.

Thionyl chloride (2.4 ml, 33.6 mmol) was added dropwise to (R)-3-bromo-2-hydroxy-2-methylpropionic acid (5.11).Gram, 28 mmol) in a solution of 30 ml of THF,The temperature of the drop is controlled at 0-12 C.It takes 10 minutes.The resulting mixture was stirred under the same conditions for 2 hours.The internal temperature was adjusted to about -5 C, and triethylamine (Et3N) (5.0 ml, 36.4 mmol, 1.3 eq) was slowly added to the reaction mixture, and the internal temperature was lower than 12 C during the addition.Stir for 20 minutes under the same reaction conditions.Then, a solution of 4-cyano-3-trifluoromethyl-phenylamine (4.0 g, 21 mmol) in 40 mL of THF was added dropwise, and the mixture was stirred at 50 C for two hours.The reaction solution was cooled to 20 ± 5 C, then water (15 ml, 2.9 vol) and toluene (20 ml, 4.0 vol) was added, and after stirring, the mixture was separated and the organic phase was washed with water (15 ml, 2.9 vol.). After the combination, it was concentrated to 5 ± 0.5 volume (6.4% by weight) by distillation under reduced pressure, and the temperature was kept below 50 C during the distillation. Add toluene (31 ml, 6 volumes) to the concentrate, dilute to 5 ± 0.5 volume (6.4 wt), adjust the temperature to 2.5 ± 2.5 C, stir at this temperature for one hour, add seed crystal (0.018 g, 0.005 wt) Stirring was continued for one hour, filtered, and the filter cake was washed twice with toluene (8.5 ml each time, 1.7 volumes each time). The batch is then dried in a vacuum oven.Get 5.8 grams(R)-3-Bromo-N-(4-cyano-3-trifluoromethyl-phenyl)-2-hydroxy-2-methylpropanamide.Yield 59%, HPLC (mobile phase is water and acetonitrile) purity 99% (220 nm), 99% (254 nm), optical HPLC purity 99%.

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; Yang Guohong; He Junze; Duan Meijuan; (34 pag.)CN108558760; (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. 22364-68-7, name is 2-(o-Tolyl)acetonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-(o-Tolyl)acetonitrile

General procedure: General: To a solution of phenylacetonitrile 1 (1.0 eq) in methyl formate (10 eq), THF was added. In anhydrous condition, solution of NaH (1.25 eq) in THF was added dropwise to the reaction mixture at 0 C and the resulting mixture was stirred at room temperature overnight. After the reaction, the mixture was quenched with H2O, and several drops of 1 N HCl were added until the pH of the solution is lowered to 4 to 5. Then the mixture was extracted with methylene chloride and dried with MgSO4. After filtration and evaporation, the resulting solution was concentrated under vacuum to give the product 2 as yellowish oil in 72%-100% yields.

The synthetic route of 22364-68-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Kim, Youngjae; Kim, Jeeyeon; Kim, Sora; Ki, Yooran; Seo, Seon Hee; Tae, Jinsung; Ko, Min Kyung; Jang, Hyun-Seo; Lim, Eun Jeong; Song, Chiman; Cho, Yoonjeong; Koh, Hae-Young; Chong, Youhoon; Choo, Il Han; Keum, Gyochang; Min, Sun-Joon; Choo, Hyunah; European Journal of Medicinal Chemistry; vol. 85; (2014); p. 629 – 637;,
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Related Products of 332-25-2, 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. 332-25-2, name is 4-(Trifluoromethoxy)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Hydroxylamine hydrochloride (2.8 g, 40 mmol),Sodium carbonate (2.7 g, 26 mmol) was dissolved in water (33 mL)4-Trifluoromethoxybenzonitrile (3.0 g, 16 mmol) andEthanol (17 mL) and heated at reflux for 6 hours.After cooling to room temperature, it was extracted with ethyl acetate (2 x 100 mL)The organic layers were combined, washed with saturated NaCl,Anhydrous Na2SO4 dried,The solvent was recovered to give 3.1 g of white powder in 89percent yield;

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

Reference:
Patent; Zhejiang University; Sheng Rong; Hu Yongzhou; Cao Ji; Li Shan; Qiu Ni; Zhao Mengdan; Yang Bo; He Qiaojun; (33 pag.)CN106366078; (2017); A;,
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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 21423-84-7 as follows. category: nitriles-buliding-blocks

Reference Example 148 Production of ethyl 2-chloro-4-methylbenzoate A mixture of 2-chloro-4-methylbenzonitrile (5.5 g, 36.28 mmol), conc. sulfuric acid (30 mL) and ethanol (30 mL) was heated under reflux for 22 hr. The reaction mixture was ice-cooled, and neutralized with 8N aqueous sodium hydroxide solution, and ethanol was evaporated. The residue was extracted with ethyl acetate, and the extract was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was diluted with ethyl acetate-hexane (1:10, 120 mL). The insoluble material was filtered off, and the filtrate was under reduced pressure and concentrated to give the title compound (3.23 g, 45%) as a pale-brown liquid. 1H NMR (300 MHz, DMSO-d6) delta:1.31 (3 H, t, J = 7.1 Hz), 2.35 (3 H, s), 4.30 (2 H, q, J = 7.1 Hz), 7.26 (1 H, d, J = 7.8 Hz), 7.41 (1 H, s), 7.71 (1 H, d, J = 7.8 Hz).

According to the analysis of related databases, 21423-84-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP2471789; (2012); A1;,
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Related Products of 654-70-6,Some common heterocyclic compound, 654-70-6, name is 4-Cyano-3-trifluoromethylaniline, molecular formula is C8H5F3N2, 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.

687 g of 4-amino-2-(trifluoromethyl)benzonitrile with 311 mul of thiophosgene in 4 ml of N,N-dimethylformamide was stirred for one hour at room temperature under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, washed with water and then concentrated by evaporation in a vacuum. The thus obtained crude isothiocyanate was combined with the cyanoamine that was produced and filtered by two hours of stirring from 743 mul of acetone cyanohydrin with 930 mg of 1,1-dimethylethyl 4-(2-aminoethyl)piperazine-1-carboxylate and 406 mg of a molecular sieve 3 A in 20 ml of tetrahydrofuran at room temperature, and it was heated to boiling for one hour with 0.57 ml of triethylamine in 40 ml of tetrahydrofuran. After concentration by evaporation in a vacuum, the title compound was obtained as a crude product, which was immediately further reacted.

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

Reference:
Patent; Schering AG; US2004/9969; (2004); A1;,
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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. 102151-33-7, name is 3-Chloro-4-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-Chloro-4-methoxybenzonitrile

To a solution of 3-chloro-4-methoxybenzonitrile (500 mg, 3.30 mmol) in 10 ml ethanol was added hydroxylammonium chloride (311 mg, 4.0 mmol) and triethylamine (392 mg, 4.0 mmol) and then the reaction mixture was stirred 16 h at 50 C. After cooling to RT, the solvent was evaporated and the crude – – was solved in ethyl acetate and dichloromethane and extracted with water. The organic phase was dried over magnesium sulfate, filtered and evaporated under vacuum to yield the title compound (124 mg, 19 % of theory). LC-MS (method 3B): RT = 0.79 min, m/z = 201 (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; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HAssFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUss, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; HEIERMANN, Joerg; HENGEVELD, Willem Jan; (764 pag.)WO2016/71216; (2016); 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. 79463-77-7, name is Diphenyl N-cyanocarbonimidate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C14H10N2O2

To a stirred solution of intermediate 11 (0.5g, 1.996 mmol) and diphenyl cyanocarbonimidate (0.475 g, 1.996 mmol) in acetonitrile (30 mL) was added triethylamine (0.0.833 mL, 5.988 mmol) at RT and stirred for l6h at RT. After completion of reaction, the reaction mixture was concentrated under reduced pressure. The residue obtained was purified by combiflash column on silica gel (hexanes/ethyl acetate=75/25) to give the title compound (0.5 g, 70%). LCMS: m/z 358.2 [M]+

According to the analysis of related databases, 79463-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; CHIKKANNA, Dinesh; KHAIRNAR, Vinayak V.; RAMACHANDRA, Muralidhara; SATYAM, Leena Khare; (139 pag.)WO2019/142126; (2019); A1;,
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