Month: April 2021

Adding a certain compound to certain chemical reactions, such as: 194853-86-6, name is 4-Fluoro-2-(trifluoromethyl)benzonitrile, 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 194853-86-6, Quality Control of 4-Fluoro-2-(trifluoromethyl)benzonitrile

4-fluoro-2-trifluorobenzonitrile (55) (994 mg),5,5-dimethylhydantoin (56) (3.37 g),Potassium carbonate (1.11 g) was added to N, N-dimethylformamide (15 mL) and stirred under nitrogen atmosphere at 45 C. for 42 hours.After returning the reaction solution to room temperature, the reaction solution was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel flash column chromatography (developing solvent: chloroform: methanol = 50: 1) to give the title compound (57) (503 mg, yield 32.2%) as a white solid.

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

Reference:
Patent; Kyoto prefectural public university; Suzuki, Takasada; Ito, Yukihiro; Ota, Yosuke; (55 pag.)JP2017/71567; (2017); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 5414-21-1,Some common heterocyclic compound, 5414-21-1, name is 5-Bromovaleronitrile, molecular formula is C5H8BrN, 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.

Into a four-necked reactor equipped with a thermometer,In a nitrogen stream,5.0 g (30.3 mmol) of 2-hydrazinobenzothiazole was added,Was dissolved in 100 ml of DMF.To this solution were added 20.9 g (152 mmol) of potassium carbonate,5.17 g (30.3 mmol) of 5-bromovaleronitrile was added,And the mixture was stirred at 60 C. for 8 hours.After completion of the reaction,The reaction solution was cooled to 20 C.,The reaction solution was poured into 500 mL of water,And extracted with 500 ml of ethyl acetate.The ethyl acetate layer was dried over anhydrous sodium sulfate.After filtering off sodium sulfate,Ethyl acetate was distilled off under reduced pressure on a rotary evaporator to obtain a yellow solid. This yellow solid was purified by silica gel column chromatography (n-hexane: ethyl acetate = 60: 40) to obtain 3.41 g of Intermediate J (yield: 45.7 mol%) as a white solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromovaleronitrile, its application will become more common.

Reference:
Patent; ZEON CORPORATION; SAKAMOTO, KEI; OKUYAMA, KUMI; KIRIKI, SATOSHI; (84 pag.)JP2017/206504; (2017); A;,
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Electric Literature of 64248-64-2, The chemical industry reduces the impact on the environment during synthesis 64248-64-2, name is 2,5-Difluorobenzonitrile, I believe this compound will play a more active role in future production and life.

In a 3 L5 4-necked flask that had been evacuated and back-filled with argon, 2,5- difluorobenzonitrile (295.3 ml, 812.0 mmol) and 4-amino-3-methylphenol (100.0 g, 812.0 mmol) were dissolved in dry DMSO (2.75 M) with rapid stirring at room temperature. The solution was evacuated/backfilled with argon (3x). Potassium carbonate (185.2 g, 1340 mmol) (-325 mesh) was added. The reaction mixture was evacuated/backfilled with argon (3x) and warmed to 80 0C (internal probe) for 16 hours. TLC indicated complete conversion. The reaction mixture was cooled to room temperature and poured slowly into 2 L of ice water with rapid stirring. The residue in the round bottom flask was taken up in water repeatedly and poured into the ice water until a total volume of 3 L was achieved and all solids were in the ice water. The suspension was stirred rapidly for 2 hours as it came to room temperature. The brown solids were collected by filtration, washed with water (3 L), air dried, dried with latex dam, and dried under high vacuum at 40 0C for 44 hours to provide 194 g (99 %) of the desired product as a tan solid. MS (APCI +) m/z 243 (M+l) was detected. 1H NMR (400 MHz5 CDCl3) delta 7.38 (m, IH), 7.18 (m5 IH), 6.65-6.85 (m, 5H), 3.60 (br, 2H), 2.17 (s, 3H).

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, 2,5-Difluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ARRAY BIOPHARMA INC.; GRONEBERG, Robert; BURGESS, Laurence, E.; HARVEY, Darren; LAIRD, Ellen; MUNSON, Mark; RIZZI, James; RODRIGUEZ, Martha; EARY, Charles, Todd; WATSON, Daniel; WO2007/89646; (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. 127667-01-0, name is 2-Fluoro-5-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 127667-01-0

2-Fluoro-5-methoxy benzonitrile (70 mg, 0.46 mmol, 1.0 equiv.) and hydrazine monohydrate (0.3 ml, 6.0 mmol, 13.0 equiv.) were mixed in n-BuOH (2 ml) and heated the reaction mixture in a microwave oven at 180 0C for 45 mins. After it cooled to room temperature, the product indazole amine was precipitated (purified) by addition of n-hexane or n-heptane solvent. Further the precipitated solid was purified using MeOH: CH2Cl2 (1 :1) solvent. The solid was washed with little water (to remove the excess hydrazine), and was dried for couple of hours to obtain nice crystalline white solid of indazole amine (46 mg) in 60 % yield. HPLC: Shim-pack VP ODS 4.6 x 50 m column, Water: MeOH; 0.1% TFA, RT =1.38; LC-MS; M+H+ = 164.2.

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; LEXICON PHARMACEUTICALS, INC.; WO2008/89307; (2008); A2;,
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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. 55877-79-7, name is 5-Chloro-2-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 55877-79-7

General procedure: 2-Ethylbenzonitrile (7.6mmol) and KOH (24.8mmol) were suspended in ethane-1,2-diol (10mL) and stirred at 170C for 7h. Then, the reaction mixture was cooled down to rt, H2O (50mL) was added and the resulting mixture was extracted three times with ether (30mL). pH of the aqueous layer was adjusted to 1 by diluted HCl and the aqueous phase was extracted three times with ether (40mL). Organic phases were collected, extracted three times with H2O (40mL) and dried over Na2SO4. The solvent was removed and obtained compound was directly used in the next step. Yield: 89.0%, white solid; mp: 64-65C; IR: 3400-2300 (b, OH), 2977 (as CH3), 2955 (as CH2), 2869 (s CH3), 1681 ( CO), 1601, 1575, 1488, 1447 ( CC aromatic) cm-1; 1H NMR (DMSO-d6, 300MHz): delta 12.79 (1H, br s, COOH), 7.76 (1H, d, J=7.0Hz), 7.43 (1H, t, J=7.5Hz), 7.33-7.21 (2H, m), 2.90 (2H, q, J=7.4Hz, CH2), 1.14 (3H, t, J=7.4Hz, CH3); 13C NMR (DMSO-d6, 75MHz): delta 169.14, 145.12, 131.96, 130.54, 130.35, 130.34, 126.04, 27.03, 16.32.

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 55877-79-7.

Reference:
Article; Kozic, Jan; Novak, Zden?k; ?imal, Vaclav; Profant, Vaclav; Kune?, Ji?i; Vin?ova, Jarmila; Tetrahedron; vol. 72; 17; (2016); p. 2072 – 2083;,
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Reference of 118431-88-2, 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. 118431-88-2, name is 3-Cyclopropyl-3-oxopropanenitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

N-(3-Cyclopropyl-1-(2-methoxyethyl)-1H-pyrazol-5-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine (Cpd No. 266) Step 1: 3-Cyclopropyl-3-oxopropanenitrile (1.4 g, 8 mmol) and 2-methoxyethyl hydrazine-HCl (1.0 g, 8.0 mmol) were mixed in ethanol (20 mL) and heated at reflux for overnight. The reaction mixture was cooled to room temperature and ethanol was removed on a rotary evaporator. Water was added and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated on a rotary evaporator. The remaining residue was purified by flash column chromatography to yield 3-cyclopropyl-1-(2-methoxyethyl)-1H-pyrazol-5-amine in 0.89 g (4.92 mmol, 62% yield). 1H NMR (CDCl3, 300 MHz): 5.12 (s, 1H), 4.12-4.06 (m, 2H), 3.95 (s, 2H), 3.70-3.64 (m, 2H), 3.32 (s, 3H), 1.95-1.70 (m, 1H), 0.90-0.80 (m, 2H), 0.70-0.60 (m, 2H). ESI-MS calculated for C9H16N3O [M+H]+=182.13, Observed: 182.50.

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

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; Wang, Shaomeng; Zhao, Yujun; Zhou, Bing; Aguilar, Angelo; Liu, Liu; Bai, Longchuan; McEachern, Donna; Sun, Duxin; Wen, Bo; Luo, Ruijuan; Zhao, Ting; Chinnaiyan, Arul; Asangani, Irfan A.; Stuckey, Jeanne; Meagher, Jennifer Lynn; Ran, Xu; US2015/246923; (2015); A1;,
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Reference of 134227-45-5, These common heterocyclic compound, 134227-45-5, name is 3,4,5-Trifluorobenzonitrile, 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.

A mixture of 8-(pirhoeridin-3-ylacetyl)-8-azabicyclo[3.2.1]octan-3-ol hydrochloride (0.035 g, 0.00012 mol), 3,4,5-trifiuorobenzonitrile (0.0209 g, 0.000133 mol) and potassium carbonate (0.0419 g, 0.000303 mol) in N,N-dimethylformamide (0.700 mL, 0.00904 mol) was heated at 100 0C overnight. After quenched with water, the mixture was extracted with EtOAc. The organic layers were combined, washed with water and brine successively, dried, and evaporated to dryness. The residue was purified on RP-HPLC to give the desired product (36 mg 77%). LCMS (M+H) 390.2. The product was believed to have a 3-endo configuation based on the starting materials.

Statistics shows that 3,4,5-Trifluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 134227-45-5.

Reference:
Patent; INCYTE CORPORATION; WO2007/89683; (2007); A1;,
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Related Products of 30041-95-3, These common heterocyclic compound, 30041-95-3, name is Ethyl 2-(4-cyanophenoxy)acetate, 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.

General procedure: Intermediates 14 were prepared by following the knownprocedure [22, 29, 30]. The mixture of ethyl 2-chloroacetate(1 mmol), substituted phenols (1 mmol), and K2CO3(1.2 mmol) in acetonitrile was stirred in refluxing for 2 h(the course of the reactions was monitored by TLC), thenfiltered, and the mother liquid was evaporated in vacuo toafford corresponding substituted ethyl 2-phenoxyacetates,which were then reacted with hydrazine hydrate (80%) toyield substituted 2-phenoxyacetohydrazides 14 in>90%yield.

The synthetic route of 30041-95-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Yanyan; Lu, Xiumian; Shi, Jun; Xu, Jiahong; Wang, Fenghua; Yang, Xiao; Yu, Gang; Liu, Zhiqian; Li, Chuanhui; Dai, Ali; Zhao, Yonghui; Wu, Jian; Monatshefte fur Chemie; vol. 149; 3; (2018); p. 611 – 623;,
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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. 60702-69-4, name is 2-Chloro-4-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H3ClFN

a) (2S)-2-[(3-Chloro-4-cyanophenyl)amino]-4-[(1,1-dimethylethyl)oxy]-4-oxobutanoic acid2-Chloro-4-fluorobenzonitrile (2.13 g, 13.8 mmol), (2S)-2-amino-4-[(1,1-dimethylethyl)oxy]-4-oxobutanoic acid (2.6 g, 13.8 mmol) and NaHCO3 (3.5 g, 41.4 mmol) in DMSO (70 mL) and H2O (10 mL) were stirred at 95 C. for 15 h. After cooling, the reaction mixture was diluted with H2O (100 mL) and washed with Et2O (100 mL). The H2O layer was acidified to Congo Red midpoint and extracted with Et2O (2¡Á). The combined organic extracts were washed with H2O, dried over Na2SO4, filtered, and concentrated to give the titled product (3.59 g, 80%) as a foam. 1H-NMR (CDCl3) delta: 1.45 (9H, s), 2.89 (2H, m), 3.54 (1H, m), 4.42 (1H, m), 6.55 (1H, d, J=8.8 Hz), 6.70 (1H, s), 7.43 (1H, d, J=8.4 Hz). LC-MS (ES) m/e 325.4 (M+H)+.

According to the analysis of related databases, 60702-69-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; WASHBURN, David G.; HOANG, Tram H.; US2008/39517; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 612-24-8,Some common heterocyclic compound, 612-24-8, name is 2-Nitrobenzonitrile, molecular formula is C7H4N2O2, 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: To a suspension of a respective 2-nitro-benzonitrile 3a,b or 7a,b (15 mmol) in water (10 mL) was added sodium dithionite (60 mmol), and the reaction mixture was heated to 50C and stirred at this temperature for 3-4 h. Then, the temperature was raised to 65C and concentrated HCl (5 mL) was added dropwise in 30 min. The resulting mixture was cooled to 20C, and the pH was adjusted to ~10 using 50% aqueous sodium hydroxide solution. The formed precipitate was filtered, washed with cold water, n-hexane, and dried at 40oC to afford 2-nitro-benzonitriles 8a-d, respectively.

The synthetic route of 612-24-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Le-Nhat-Thuy, Giang; Dinh, Thuy Van; Pham-The, Hai; Nguyen Quang, Hung; Nguyen Thi, Nga; Dang Thi, Tuyet Anh; Hoang Thi, Phuong; Le Thi, Tu Anh; Nguyen, Ha Thanh; Nguyen Thanh, Phuong; Le Duc, Trung; Nguyen, Tuyen Van; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3741 – 3747;,
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