Tag: M.W=100-200

Related Products of 6306-60-1,Some common heterocyclic compound, 6306-60-1, name is 2-(2,4-Dichlorophenyl)acetonitrile, molecular formula is C8H5Cl2N, 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.

Preparation of alpha-(2,4-dichlorophenyl)-alpha-hydroxymethylene acetonitrile 0.6 g of metal sodium was added to dry ethanol to obtain an ethanol solution of sodium ethoxide. Then, a mixed liquid comprising 37.2 g of 2,4-dichlorophenyl acetonitrile and 22.2 g of ethyl formate, was added thereto under heating to 70 C. After the addition, the mixture was further heated and refluxed for 2 hours and then, left to stand for 1 day. The reaction solution was cooled to 0 C. and then subjected to filtration. After washing with diethyl ether, the sodium salt collected by filtration was added to 130 ml of distilled water, and 9 ml of acetic acid was dropwise added thereto under cooling at 0 C. After the dropwise addition, the mixture was stirred at room temperature for about 30 minutes. Then, the formed precipitate was collected by filtration and washed with water. It was dried to obtain 31.7 g (yield: 74%) of the desired product. Melting point: 162-163 C.

The synthetic route of 6306-60-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kumiai Chemical Industry Co., Ltd.; Ihara Chemical Industry Co., Ltd.; US6048823; (2000); A;,
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Application of 194853-86-6, 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 194853-86-6 as follows.

Potassium carbonate (304 mg, 2 .2 mmol) was dissolved in a minimum amount of water. Next, 4-fluoro-2-trifluoromethylbenzonitrile (378 mg, 2.0 mmol) and trans-4- aminocyclohexanol (460 mg, 4.0 mmol) dissolved in acetonitrile (10 mL) were added. The resulting mixture was then heated at 80C for 3 days. After cooling at room temperature, the mixture was concentrated under vacuum, taken up in ethyl acetate (15 mL), washed with saturated aqueous ammonium chloride (2×10 mL), and washed with water (10 mL). The organic phase was collected and dried over sodium sulfate, filtered, and concentrated under vacuum. The desired product was isolated as a colorless solid (456 mg, 80% yield).

According to the analysis of related databases, 194853-86-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INTERVET INTERNATIONAL B.V.; WO2009/77527; (2009); A1;,
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Synthetic Route of 123-06-8, 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. 123-06-8, name is Ethoxymethylenemalononitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of t-butylhydrazine hydrochloride (4.67 g, 53 mmol) and triethylamine (5.35 g, 53 mmol) in anhydrous ethanol (250 ml) was stirred and ethoxymethylene malononitrile (6.47 g, 53 mmol) was slowly added in portions. The mixture was heated at reflux for 3 hr. The solvent was removed in vacuo and the product was crystallized from ethyl acetate – hexane followed by ether to afford 5-amino-l-tert-butyl-lH-pyrazole-4-carbonitrile as light pale brown crystals (5.6 g, 34.1 mmol); LC/MS, API-ES, Neg, (M-H)”, 163.0.

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, Ethoxymethylenemalononitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FOLDRX PHARMACEUTICALS, INC.; WO2009/62118; (2009); A2;,
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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. 874-89-5, name is 4-(Hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., Safety of 4-(Hydroxymethyl)benzonitrile

General procedure: To 16 mL of acetonitrile/water (1:1 v/v) mixture was added 0.5-1.2 mmol of the starting compound. The contents were heated at reflux with introduction of oxone (cf. entries for each case) incrementally over the entire duration of the reaction. For secondary benzyl halides, the reactions were run at room temperature. The progress of the reaction in each case was monitored by TLC analysis. After completion of the reaction, the reaction mixture was cooled to room temperature and the organic matter was extracted with ethyl acetate. The combined organic extract was dried over anhyd Na2SO4 and concentrated in vacuo. Short pad silica gel column chromatography of the residue led to isolation of the pure product.

The synthetic route of 874-89-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Parida, Keshaba Nanda; Jhulki, Samik; Mandal, Susovan; Moorthy, Jarugu Narasimha; Tetrahedron; vol. 68; 47; (2012); p. 9763 – 9768,6;; ; Article; Parida, Keshaba Nanda; Jhulki, Samik; Mandal, Susovan; Moorthy, Jarugu Narasimha; Tetrahedron; vol. 68; 47; (2012); p. 9763 – 9768;,
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34403-48-0, name is 4-((Methylamino)methyl)benzonitrile, 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. Formula: C9H10N2

To a solution of compound 222 (1 mmol), Aldehyde/ketone (1 mmol), in THF was added NaBH3CN (2 mmol). The reaction mixture was stirred at room temperature overnight. After disappearance of the starting material as indicated by TLC, a solution of saturated NH4C1 solution (5 mL) was added dropwise at room temperature. The mixture was then diluted with Et20 (30 mL) and washed three times with water (30 mL), and brine (30 mL). Organic layer was dried over Na2S04, concentrated under vacuum, and the residue was purified by column chromatography to provide compound 223.

The synthetic route of 34403-48-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHWESTERN UNIVERSITY; SILVERMAN, Richard, B.; WANG, Hua; KHANFAR, Mohammad; WO2014/100833; (2014); A1;,
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Synthetic Route of 177476-76-5, These common heterocyclic compound, 177476-76-5, name is 4-Amino-3-methoxybenzonitrile, 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: Step (A): To a solution of racemic (2?S,3?R,4?S,5?R)-6-chloro-4?-(3-chloro-2-fluoro-phenyl)-2?-(2,2-dimethyl-propyl)-2-oxo-1,2-dihydro-spiro[indole-3,3?-pyrrolidine]-5?-carboxylic acid trifluoroacetic acid salt 17 (R3 = H, R1 = CH2C(CH3)3, Ref. 29) (0.2 g, 0.36 mmol) in dichloromethane (10 mL) was added diisopropylethylamine (0.18 g, 1.4 mmol), diphenylphosphinic chloride (Aldrich) (0.25 g, 1.1 mmol), respectively. The mixture was stirred at room temperature for 0.5 h, then methyl 4-amino-2-methoxybenzoate (Acros) (0.077 g, 0.43 mmol) or methyl 4-amino-3-methoxy-benzoate (Ark Pharm) (0.16 g, 0.9 mmol) was added. The reaction mixture was stirred at room temperature for 20 h. The mixture was concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was separated, washed with water, brine, dried over Na2SO4, then concentrated. The residue was purified by chromatography (3-20% of EtOAc in CH2Cl2) to give a white solid (yield 0.12 g, 54%).

Statistics shows that 4-Amino-3-methoxybenzonitrile is playing an increasingly important role. we look forward to future research findings about 177476-76-5.

Reference:
Article; Zhang, Zhuming; Ding, Qingjie; Liu, Jin-Jun; Zhang, Jing; Jiang, Nan; Chu, Xin-Jie; Bartkovitz, David; Luk, Kin-Chun; Janson, Cheryl; Tovar, Christian; Filipovic, Zoran M.; Higgins, Brian; Glenn, Kelli; Packman, Kathryn; Vassilev, Lyubomir T.; Graves, Bradford; Bioorganic and Medicinal Chemistry; vol. 22; 15; (2014); p. 4001 – 4009;,
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Synthetic Route of 5922-60-1, These common heterocyclic compound, 5922-60-1, name is 2-Amino-5-chlorobenzonitrile, 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: To a solution of 2-cyano-4-chloroaniline 3g (19.6 mmol) in 30 mL of AcOH was added dropwise 1,2 mL (23.6 mmol) of bromine and the resulting mixture was stirred at 50 oC overnight. The resulting precipitate was filtered by suction on a glass frit, washed with H2O and dry under vacuum. The solid was then added by portion to a hot (50 oC) stirred solution of isoamyle nitrite 10 mL in 10 mL of DMF. After 10 min the mixture was cooled to room temperature and poured into 100 mL of HCl 3N, subject to extraction with AcOEt (3 X 40 mL), dry over Na2SO4 and concentrated on a rotary evaporator. Purification of the residue by column chromatography yielded 2.08g (49 %) 9c as a white solid1H NMR (CDCl3), d = 7.50 (t, 1H, J=2.0 Hz, CHAr); 7.60 (t, 1H, J=2.0 Hz, CHAr); 7.65 (t, 1H, J=2.0 Hz, CHAr). 13C NMR (CDCl3), d = 115.6 (1C, Cq); 166.4 (1C, Cq); 123.8 (1C, Cq); 131.0 (1C, CHAr); 133.4 (1C, CHAr).

Statistics shows that 2-Amino-5-chlorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 5922-60-1.

Reference:
Article; Alagille, David; Dacosta, Herve; Chen, Yelin; Hemstapat, Kamondanai; Rodriguez, Alice; Baldwin, Ronald M.; Conn, Jeffrey P.; Tamagnan, Gilles D.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3243 – 3247;,
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Adding a certain compound to certain chemical reactions, such as: 67515-59-7, name is 4-Fluoro-3-(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 67515-59-7, Quality Control of 4-Fluoro-3-(trifluoromethyl)benzonitrile

4-Fluoro-3-(trifluoromethyl)benzonitrile (2.0g, 10.58mmol) was dissolved in dimethyl acetamide (35mL), morpholine (2.88mL, 31.73mmol) was added thereto, and the mixture was subjected to a reaction at 145C for 19 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (50mL), and the organic layer was washed with an aqueous sodium hydrogen carbonate solution (50mL). The organic layer was washed with water, dried with sodium sulfate, and the solvent was distilled under reduced pressure. The concentrated mixture was crystallized with ethyl acetate (lOmL) and n-hexane (80mL) to obtain the title compound as a brown solid (2.1g).1H NMR (DMSO-d6) delta 8.17 (s, 1H), 8.08 (d, 1H), 7.58 (d, 1H), 3.71 (m, 4H), 2.99 (m, 4H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-3-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; HANMI HOLDINGS CO., LTD.; KOREA INSTITUTE OF SCIENCE AND TECHNOLOGY; CATHOLIC UNIVERSITY INDUSTRY ACADEMIC COOPERATION FOUNDATION; SON, Jung Beom; JUNG, Seung Hyun; CHOI, Wha Il; JUNG, Young Hee; CHOI, Jae Yul; SONG, Ji Yeon; LEE, Kyu Hang; LEE, Jae Chul; KIM, Eun Young; AHN, Young Gil; KIM, Maeng Sup; CHOI, Hwan Geun; SIM, Tae Bo; HAM, Young Jin; PARK, Dong-sik; KIM, Hwan; KIM, Dong-Wook; WO2011/93684; (2011); A2;,
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Application of 59997-51-2, A common heterocyclic compound, 59997-51-2, name is 4,4-Dimethyl-3-oxopentanenitrile, molecular formula is C7H11NO, 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.

128 mL of water was added to 50 g (357 mmol) of the intermediate (c), and the mixture was stirred at room temperature, 98.2 g (785 mmol) of pivaloyl acetonitrile was added to this suspension, 12M hydrochloric acid water was added dropwise at the same temperature so that the pH became 3, The mixture was heated to an internal temperature of 50 C. and stirred at the same temperature for 6 hours. After completion of the reaction, 8N aqueous solution of calcium hydroxide was added to neutralize the solution to pH 6.4. The crystals thus precipitated were collected by filtration and washed with water until the inner temperature became 10 C. The obtained crystals were dried under reduced pressure at 60 C. and 30 mL of toluene was added to the obtained crude product In addition, it was dissolved by heating to 60 C. The resulting solution was allowed to stand at room temperature for 12 hours, and the precipitated crystals were collected by filtration, washed with cold toluene, dried at 60 C. under reduced pressure,The obtained intermediate (d) was obtained in 87.7 g (white powder, yield 69.3%), and the NMR measurement results of the obtained intermediate (d) are as follows.

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; FUJIFILM Corporation; Tateishi, Keiichi; Sasaki, Hiroki; Nagata, Yoshiaki; (37 pag.)JP2017/61660; (2017); 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. 243128-37-2, name is 4-Fluoro-3-methoxybenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., name: 4-Fluoro-3-methoxybenzonitrile

4-Fluoro-3-methoxybenzonitrile (98.2 g, 0.65 mol) was combined with 4-methyl-1 /-/- imidazole (53.4 g, 0.65 mol) and anhydrous potassium carbonate (138.2 g, 1 mol, 1.54 eq) in dimethylformamide (650 ml_), and the reaction mixture was stirred for 16 hours at 135-140 0C (internal temperature). The mixture was cooled to room temperature and filtered; the salts were washed with dichloromethane (3 x 30 ml_). The combined filtrates were evaporated in vacuo to afford a brown semisolid, which was suspended in water (500 ml_) and left to stand at 5 0C for 24 hours. The mixture was filtered, and the solid was washed with ice water (2 x 50 ml_), then dried in vacuo to afford a yellow solid (105.5 g). Crystallization from methanol (106 ml_) provided purified product (66.3 g) as yellowish crystals. These were boiled with acetone (100 ml_) for 5 minutes and the mixture was left to cool overnight. The mixture was filtered, and the crystals were washed with acetone (2 x 10 ml_) to afford the title compound as a white solid. Yield: 54.6 g, 0.256 mmol, 39%. 1H NMR (400 MHz, CDCI3) delta 2.31 (d, J=1.0 Hz, 3H), 3.94 (s, 3H), 6.97 (m, 1 H), 7.30 (m, 1 H), 7.37 (m, 2H), 7.79 (d, J=1.4 Hz, 1 H).

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 243128-37-2.

Reference:
Patent; PFIZER INC.; ALLEN, Martin, Patrick; AM ENDE, Christopher, William; BRODNEY, Michael, Aaron; DOUNAY, Amy, Beth; JOHNSON, Douglas, Scott; PETTERSSON, Martin, Youngjin; SCHWARZ, Jacob, Bradley; TRAN, Tuan, Phong; WO2010/100606; (2010); A1;,
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