Month: May 2021

Reference of 420-04-2, These common heterocyclic compound, 420-04-2, name is Cyanamide, 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.

(1) Ethyl N-cyanoacetoimidate A solution of cyanamide (3.52 g), acetic anhydride (15.7 ml) and triethyl orthoacetate (15.0 ml) was stirred at 140 C. for 2.5 hours. After the reaction, the mixture was distilled under reduced pressure to give 5.29 g of a colorless transparent liquid (yield 58%). Boiling point: 50-60 C./2.5 mmHg IR (KBr): 2990, 2940, 2210, 1700, 1668, 1604 cm-1 1 H-NMR (CDCl3) delta: 1.35 (3H, t, J=7.1 Hz), 2.40 (3H, s), 4.29 (2H, q, J=7.1 Hz)

Statistics shows that Cyanamide is playing an increasingly important role. we look forward to future research findings about 420-04-2.

Reference:
Patent; The Green Cross Corporation; US5750545; (1998); 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. 420-04-2, name is Cyanamide, A new synthetic method of this compound is introduced below., name: Cyanamide

0.2 mol of the above intermediate and 0.2 mol of 50% monocyanamide aqueous solution were added, stirred uniformly, and 0.1 mol of anhydrous sodium hydrogen phosphate was added under stirring at room temperature to control the reaction temperature not exceeding 40 C, and the reaction time was 4 h, and analyzed by thin layer chromatography. The reaction progress was followed; after the reaction was completed, the filtration was carried out, the filter residue was washed with distilled water, and the washing water and the filtrate were combined, shaken, and allowed to stand for stratification; the aqueous layer was separated, and the aqueous layer was extracted with ethyl acetate three times. The ethyl acetate layer was combined with the oil layer and distilled under reduced pressure at 80 kPa for 2 h. A colorless clarified oil was obtained as the product, ethyl N-cyanoethyl imidate, yield: 95.3%.

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; Zhang Yu; (4 pag.)CN109721509; (2019); 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. 191014-55-8, name is 4-Fluoro-2-methoxybenzonitrile, A new synthetic method of this compound is introduced below., name: 4-Fluoro-2-methoxybenzonitrile

To a mixture of 4-fluoro-2-methoxybenzonitrile, (800 mg, 5.3 mmol) and conc.HCl (0.53 mL, 6.36 mmol, 1.2 eq.) in ethanol (20 mL) was added 10% Pd-C (100 mg; Aldrich), and the mixture hydrogenated at 1 atm hydrogen for 15 hrs at room temperature. To this mixture was added an additional amount of conc.HCl (1 mL) and 10% Pd-C (200 mg) and the reaction allowed to continue for another 40 hrs. The mixture was filtered through Celite and the filtrate concentrated in vacuo to dryness. The residue was triturated with ether to provide the title compound (895 mg, Yield 88%) as a white powder: 1H NMR (CDCl3, 500 MHz) delta ppm: 3.84 (3H, s, OMe), 3.91 (2H, d, J=5.5 Hz, N-CH2), 6.81 (1H, dt, J=2.5 Hz, J=J=8.5 Hz, Ar-H), 6.99 (1H, dd, J=2.5 Hz, J=11.3 Hz, Ar-H), 7.47 (1H, dd, J=7 Hz, J=8.5 Hz, Ar-H); 13C NMR (CDCl3, 125.8 Hz) delta ppm: 36.76, 56.03, 99.30, 99.51 106.28, 106.45, 117.93, 117.95, 131.60, 131.69, 158.56, 158.64, 162.28, 164.22. HRMS (ESI) calcd for C8H11FNO (M+H) 156.0825, found 156.0830.

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; Bristol-Myers Squibb Company; US2007/111984; (2007); 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. 89942-45-0, name is 2-(Hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C8H7NO

General procedure: To a 100 mL two-necked flask was added substituted benzylalcohol or 4,6-dimethylpyrimidine-2-thiol (2.60 mmol), NaOH (6.40 g, 1.60 mmol) and dimethylsulfoxide (30 mL). The flask was vacuumed and flushed three times with nitrogen. Then the solutionof 8 (0.20 g, 0.87 mmol) in dimethylsulfoxide (510 mL) was added, and the resulting mixture was heated to 80 C and kept at that temperature for approximately 12 h until the completion of the reaction (monitored by TLC). Subsequently, the mixture was cooled to room temperature and diluted with ethyl acetate (100 mL). The mixture was washed with brine to pH 7, and the organic phase was dried with anhydrous sodium sulfate. The organic phase was concentrated to get crude product, which was purified by column chromatography (ethyl acetate/ petroleumether 1:30 as eluent) to get 4a-ac in yields of 27.3-75.1%.

The synthetic route of 89942-45-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lu, Huan-Huan; Xue, Ping; Zhu, Yuan-Yuan; Ju, Xiu-Lian; Zheng, Xiao-Jiao; Zhang, Xun; Xiao, Ting; Pannecouque, Christophe; Li, Ting-Ting; Gu, Shuang-Xi; Bioorganic and Medicinal Chemistry; vol. 25; 8; (2017); p. 2491 – 2497;,
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Application of 5312-97-0, 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 5312-97-0 as follows.

To solution of 2,5-dimethoxybenzonitrile (1.5 g) in dry Et2O (7 mL) was added propyl magnesium chloride (2 M in Et2O, 9.2 mL) and the resulting mixture was heated to 40 C. for 2 h. The mixture was chilled and 4 M HCl (9 mL) was carefully added and it was stirred at ambient temperature for 16 h. The mixture was extracted with EtOAc, the combined organic layers were washed with water, were dried and the volatiles were removed under reduced pressure. The residue was purified by column chromatography (Interchim cartridge 15SiHP/120 g, Cy/EtOAc) to yield the desired compound (57% yield). [0569] LC-MS (Method 1): m/z [M+H]+=209.3 (MW calc.=208.25); Rt=3.5 min

According to the analysis of related databases, 5312-97-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gruenenthal GmbH; Nordhoff, Sonja; Wachten, Sebastian; Kless, Achim; Voss, Felix; Ritter, Stefanie; US2014/194452; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 914250-82-1, name is 3-Bromo-2-chlorobenzonitrile, 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 914250-82-1, COA of Formula: C7H3BrClN

Description for D14 3-bromo-2-chloro-Lambda/-hydroxybenzenecarboximidamide (D14) A mixture of 3-bromo-2-chlorobenzonitrile (2.0 g), sodium bicarbonate (1.55 g) and hydroxylamine hydrochloride (1.28 g) in ethanol (50 ml.) was heated at reflux for overnight. The inorganic precipitate was filtered off. The solid was washed thoroughly with ethanol. The filtrate was concentrated. The obtained solid was dried in vacuo to afford 3-bromo-2-chloro-Lambda/-hydroxybenzenecarboximidamide (2.13 g). MS (ES): C7H6BrCIN2O requires 248; found 249.1 (M+H+).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; GLAXO GROUP LIMITED; DENG, Guanghui; LIN, Xichen; MENG, Qinghua; REN, Feng; XIANG, Jianing; XU, Heng; ZHAO, Baowei; ZHANG, Haibo; WO2010/148649; (2010); A1;,
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These common heterocyclic compound, 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, 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. Quality Control of tert-Butyl 4-cyanobenzylcarbamate

To a solution of hydroxylamine hydrochloride (2.24 g, 32.3 mmol) in dimethyl sulfoxide (10.6 mL), triethylamine (4.51 mL, 32.4 mmol) was added and the resulting mixture was stirred at room temperature for an hour. The precipitating salt was filtered and washed with THF. The THF was distilled off under reduced pressure and after adding the foregoing compound (n-2) (1.50 g, 6.46 mmol), the resulting mixture was stirred at 75C for 15 hours. The reaction mixture was cooled to room temperature and after adding water, extraction was conducted with ethyl acetate. The organic layer was successively washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvents were distilled off under reduced pressure to give tert-butyl 4-(N’-hydroxycarbamimidoyl)benzylcarbamate (n-3) (amount, 1.70 g; yield, 99%).

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

Reference:
Patent; Kaken Pharmaceutical Co Ltd; kegami, Satoru; Watanabe, Atsushi; Hirano, Kimio; Oyama, Tadashi; (62 pag.)KR2016/18745; (2016); A;,
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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. 34662-24-3, name is 2-Chloro-3-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Chloro-3-nitrobenzonitrile

Example 1732- [4-(l-Benzofuran-5-yl)phenyl]-l-{[(3S)-l-(cyclopropylcarbonyl)-3- pyrrolidinyl] methyl}- lH-benzimidazole-7-carbonitrile(a) 2-({[(3S)-l-(Cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}amino)-3- nitrobenzonitrileA mixture of {[(3S)-l-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}amine (553 mg, 3.29 mmol), 2-chloro-3 -nitrobenzonitrile (500 mg, 2.74 mmol), and DIEA (1.431 mL, 8.22 mmol) were dissolved in 1,4-dioxane (10 mL) in a microwave Vial. The mixture was heated at 150 C for 1 hour. The mixture was evaporated, taken up in DCM and washed with water. The aqueous layer was extracted with DCM and the combined organics evaporated and purified by silica gel column chromatography using a gradient of 0-5% MeOH/DCM to afford the titled compound (800 mg, 2.55 mmol, 93 % yield) as an orange solid. 1H NMR (400 MHz, chloroform-d) delta ppm 0.71-0.88 (m, 2 H) 0.94-1.12 (m, 2 H) 1.59-1.69 (m, 1 H) 1.69-2.00 (m, 1 H) 2.11-2.41 (m, 1 H) 2.55-2.92 (m, 0 H) 3.16-4.11 (m, 6 H) 6.80 (ddd, J=10.04, 8.40, 7.58 Hz, 1 H) 7.79 (ddd, J=9.35, 7.71, 1.39 Hz, 1 H) 8.27- 8.49 (m, 1 H) 8.53-8.80 (m, 1 H).

According to the analysis of related databases, 34662-24-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE LLC; HALLMAN, Jason; LAUDEMAN, Christopher; LIU, Ronggang; MILLER, Aaron; MOORE, Michael, Lee; DOCK, Steven; MUSSO, David; PARRISH, Cynthia; WO2011/56635; (2011); A1;,
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Application of 129931-47-1, 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. 129931-47-1, name is 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Stage 1 1-(2-chloro-6-cyano-4-trifluoromethylphenyl)-5-(2-hydroxyisopropyl)-4-trifluoromethylpyrimidin-6-one was prepared from 3-chloro-4-fluoro-5-cyano-trifluoromethylbenzene and 5-(2-hydroxyisopropyl)-4-trifluoromethyl-pyrimidin-6-one (Preparation 2) according to the general method disclosed in EP 0 398 499 for the preparation of Compound A1 in Table A1. Melting Point: 125.6 – 127.6C, 1H NMR delta(CDCl3): 8.14(s,1H); 8.05(s,1H); 7.99(s,1H); 3.45(s,1H); 1.75(d,6H).

The synthetic route of 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; IMPERIAL CHEMICAL INDUSTRIES PLC; EP481604; (1992); A1;,
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These common heterocyclic compound, 80517-21-1, name is 4-Fluoro-2-nitrobenzonitrile, 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: 4-Fluoro-2-nitrobenzonitrile

4-fluoro-2-nitrobenzonitrile (0.2 mmol, 33.2 mg), tetrahydroxydiboron (0.6mmol, 53.8 mg), glacial acetic acid (0.24mmol, 14.5mg), cuprous chloride (0.04mmol, 4.0mg), Benzaldehyde (0·24mmol, 25·4mg), methanol (1ml), water (1ml) were added to the test tube, reacted at 60 C for 3h, after the completion of reaction, the reaction solution was extracted with ethyl acetate three times, the combined organic phases are concentrated to dryness, separated through column chromatography (petroleum ether: ethyl acetate =4:1), Yield:(45.0mg,93%)

The synthetic route of 4-Fluoro-2-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; China Three Gorges University; Zhou Haifeng; Sui Yuebo; Jiang Xiaolan; Yang Bing; Yu Tao; (16 pag.)CN108558778; (2018); A;,
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