Month: July 2021

Electric Literature of 1813-33-8, These common heterocyclic compound, 1813-33-8, name is 2-Chloro-4-(trifluoromethyl)benzonitrile, 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.

2-Chloro-4-(trifluoromethyl)benzonitrile (500 mg, 2.43 mmol) was diluted with toluene (3 mL), placed under nitrogen and cooled to -78C. DIBAL-H (4865 muL, 4.86 mmol) was added dropwise and the reaction was stirred for 1 hour. The reaction was warmed to 00C and acetic acid (2 mL) was added followed by 10 mL of water. After stirring for 2 hours, the reaction was extracted twice with ethyl acetate, washed with Rochelle’s salt, dried over MgSO4, filtered and concentrated. The material was purified using a biotage 25 cartridge running a gradient, 100%hexanes to 20%DCM/hexanes to yield 2-chloro-4-(trifluoromethyl)benzaldehyde (400 mg, 1.92 mmol, 78.8 % yield) as a clear oil.

The synthetic route of 1813-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2009/158426; (2009); A1;,
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Related Products of 77326-36-4, These common heterocyclic compound, 77326-36-4, name is 2-Amino-6-fluorobenzonitrile, 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.

It was prepared as described for 8. Starting from freshly sublimed 2-amino-6-fluorobenzonitrile (918 mg, 6.75 mmol) in 1,2-dichloroethane (8 mL) and enone 7 (R9 = allyl) (800 mg, 4.50 mmol) in 1,2-dichloroethane (40 mL), and heating the reaction mixture under reflux for 16 h, a crude product (1.75 g) was obtained and subjected to column chromatography [silica gel (62 g), CH2Cl2/MeOH/25% aqueous NH4OH mixtures as eluent]. On elution with CH2Cl2/MeOH/25% aqueous NH4OH 99:1:0.05, huprine 11 (762 mg, 58% yield) was obtained as a beige solid.A solution of huprine 11 (762 mg, 2.59 mmol) in MeOH (6 mL) was treated with 1.81 N methanolic HCl (4.3 mL, 7.78 mmol) and the resulting solution was evaporated under reduced pressure. After recrystallization of the resulting solid residue from AcOEt/MeOH 15:2 (34 mL), 11·HCl was obtained as a light brown solid (570 mg), mp >300 C (dec.) (AcOEt/MeOH 15:2). IR (KBr) nu 3600-2400 (max at 3394, 3314, 3201, 3166, 3071, 3020, 2926, 2902, 2829, 2774, 2669, 2604, C-H, N-H, and N+-H st), 1640, 1593, and 1548 (ar-C-C and ar-C-N st) cm-1; 1H NMR (500 MHz, CD3OD) delta 1.98 (dm, J = 12.5 Hz, 1H, 13-Hsyn), 2.05 (br d, J ? 17.5 Hz, 1H, 10-Hendo), 2.10 (dm, J = 12.5 Hz, 1H, 13-Hanti), 2.51 (ddm, J = 17.5 Hz, J’ = 5.5 Hz, 1H, 10-Hexo), 2.63 (d, J ? 7.0 Hz, 2H, 9-CH2-CHCH2), 2.83 (m, 1H, 7-H), 2.88 (ddd, J = 18.0 Hz, J’ = J = 2.0 Hz, 1H, 6-Hendo), 3.22 (dd, J = 18.0 Hz, J’ = 5.5 Hz, 1H, 6-Hexo), 3.40 (m, 1H, 11-H), 4.86 (s, NH2 and NH+), 4.88-4.91 (complex signal, 2H, 9-CH2-CHCH2), 5.63 (dm, J = 7.0 Hz, 1H, 8-H), superimposed in part 5.65 (ddt, J = 17.0 Hz, J’ = 10.0 Hz, J = 7.0 Hz, 1H, 9-CH2-CHCH2), 7.34 (ddd, J = 14.0 Hz, J’ = 8.5 Hz, J = 1.0 Hz, 1H, 2-H), 7.57 (ddd, J = 8.5 Hz, J’ = J = 1.0 Hz, 1H, 4-H), 7.83 (ddd, J = J’ = 8.5 Hz, J = 6.0 Hz, 1H, 3-H); 13C NMR (75.4 MHz, CD3OD) delta 27.2 (CH, C11), 28.1 (CH, C7), 29.3 (CH2, C13), 34.0 (CH2, C10), 35.9 (CH2, C6), 42.5 (CH2, 9-CH2-CHCH2), 107.4 (C, d, J = 12.1 Hz, C12a), 112.2 (CH, d, J = 23.0 Hz, C2), 115.8 (C, C11a), 116.3 (CH, C4), 116.4 (CH2, 9-CH2-CHCH2), 125.7 (CH, C8), 135.0 (CH, d, J = 11.5 Hz, C3), 137.2 (CH, 9-CH2-CHCH2), 137.3 (C, C9), 140.7 (C, C4a), 152.9 (C) and 155.4 (C) (C5a and C12), 161.2 (C, d, J = 253 Hz, C1). Anal. Calcd for C19H19FN2·HCl (330.83): C, 68.98; H, 6.09; N, 8.47; Cl, 10.72. Found: C, 68.65; H, 6.20; N, 8.35; Cl, 11.14.

Statistics shows that 2-Amino-6-fluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 77326-36-4.

Reference:
Article; Defaux, Julien; Sala, Marta; Formosa, Xavier; Galdeano, Carles; Taylor, Martin C.; Alobaid, Waleed A.A.; Kelly, John M.; Wright, Colin W.; Camps, Pelayo; Munoz-Torrero, Diego; Bioorganic and Medicinal Chemistry; vol. 19; 5; (2011); p. 1702 – 1707;,
Nitrile – Wikipedia,
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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. 2032-34-0, name is 3,3-Diethoxypropanenitrile, A new synthetic method of this compound is introduced below., Quality Control of 3,3-Diethoxypropanenitrile

Preparation of 3,3-Diethoxy-2-formylpropionitrile Potassium Salt (II) To a stirred solution of 3,3-diethoxypropane-nitrile (1,283.80 g, 1.98 moles) and methyl formate (148.80 g, 2.48 moles) in anhydrous THF (1.1 L) at 10 C. was added 1.0 M potassium tert-butoxide in THF (2.2 L, 2.2 moles). Temperature was maintained in the range of 10 C. to 15 C. throughout the 45 minute addition. Following the addition, the resulting slurry was stirred 2 hours at ambient room temperature. Hexane (400 mL) was then added and stirring was continued for another 20 min. The slurry was filtered and the cake washed with 1/1 hexanes/THF and dried overnight at 60 C. in a vacuum oven. The yield of pale tan powder was 302.5 grams (73.0%).

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; Chen, Jian Jeffrey; Dunn, James Patrick; Goldstein, David Michael; Stahl, Christoph Martin; US2003/171584; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 630-18-2, name is Pivalonitrile, 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 630-18-2, Product Details of 630-18-2

General procedure: To an ice cold solution of pivalonitrile (1f, 120 muL, 1.085 mmol) in Et2O (1.0 mL)was added an ethereal solution of 2-naphthylmagnesium bromide (2b, 0.75 M, 1.88mL, 1.410 mmol) and the reaction mixture was stirred at 60 C in a sealed tube for 2 h.After cooling to 0 C, the reaction mixture was treated with anhydrous MeOH (132muL), followed by the addition of CuBr2 (24.3 mg, 0.109 mmol) and anhydrous DMF(10.0 mL). The resulting reaction mixture was stirred at 80 C under an oxygenatmosphere for 6 h. Then the reaction was quenched by the addition of pH 9ammonium buffer solution and the organic materials were extracted with Et2O. Thecombined organic extracts were washed with water, and then with brine and driedover anhydrous MgSO4. The solvents were removed in vacuo and the resulting crudematerial was purified by flash column chromatography using hexane-EtOAc (90:10)to afford 2-naphthonitrile

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

Reference:
Article; Tnay, Ya Lin; Ang, Gim Yean; Chiba, Shunsuke; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1933 – 1943;,
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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. 4426-11-3, name is Cyclobutanecarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Safety of Cyclobutanecarbonitrile

A solution of borane in THF (1M, 296 mL, 296 mmol) was added to a solution of cyclobutanecarbonitrile (20 g, 247 mmol) in THI (60 niL) under argon, and the mixture heated under reflux overnight. The mixture was cooled in an ice-water bath and MeOH (120 niL) added dropwise while keeping the temperature of the mixture below 20 C. HCI inMeOH (4M, 300 mL) was added, againkeeping the temperature below 20 C. The resulting solutionwas heated under reflux for 2.5 h. After cooling, the mixture was concentrated. The residue was diluted with MeOH (100 niL) and concentrated, and this process was repeated. Ether was added to the residue and the mixture stirred for 30 minutes before filtering to give the title compound (25.9 g, 86%) as a white solid. H NNR (300 MHz, DMSO-d6) ppm 1.70-1.86 (m, 4H) 1.97-2.04 (m, 2H) 2,46-2.61 (m, lH) 2.75-2.84 (m, 2H) 8.02 (br s, 3H)

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 4426-11-3.

Reference:
Patent; Takeda Pharmaceutical Company Limited; BUFFHAM, William; CANNING, Hannah; DAVENPORT, Richard; FARNABY, William; MACK, Stephen; PARMAR, Alka; WRIGHT, Susanne; US2015/57298; (2015); A1;,
Nitrile – Wikipedia,
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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 610-66-2 as follows. Product Details of 610-66-2

2-Nitrobenzyl cyanide (1 g, 6.2 mmol) was dissolved in 4N hydrochloric acid dioxane solution (10 ml) and ethanol (2 ml) and the mixture was stirred at room temperature for 2 days. The solvent was evaporated and the obtained crude product was dissolved in ethanol (10 ml). Ammonium carbonate (1.0 g) was added, and the mixture was stirred overnight. After filtration of ammonium carbonate, the solvent was evaporated. Toluene (10 ml), diisopropylethylamine (1.2 ml, 7.3 mmol) and 2-amino-1,1,3-tricyano-1-propene (510 mg, 4.2 mmol) were added to the obtained crude product and the mixture was stirred at 110 C. for 2 hr. A treatment according to a conventional method using ethyl acetate as an extraction solvent gave a crude product, which was successively purified by silica gel column chromatography to give a nitrile intermediate (70 mg)

According to the analysis of related databases, 610-66-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Yamada, Tatsuhiro; Nakagawa, Tadakiyo; Tanaka, Yasuhiro; Fujita, Kohichi; Tagami, Tomoyuki; Ikenoue, Yuka; Fukuda, Shunsuke; Chujo, Yoshitomo; Suzuki, Manabu; Murata, Masahiro; US2005/250796; (2005); A1;,
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6011-14-9, name is 2-Aminoacetonitrile hydrochloride, 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. Recommanded Product: 6011-14-9

2-trifluoromethylpyridine-5-carboxylic acid (0.191 g, 1.0 mmol)And aminoacetonitrile hydrochloride (0.081 g, 1.0 mmol)Dissolved in 25 mL of dichloromethane,Add triethylamine (0.202 g, 2.0 mmol),Then EDC (0.287 mg, 1.5 mmol) was added.HOBt (0.20g, 1.5mmol),Reaction at 25 C for 3 h,After TLC detects the reaction,The reaction solution was first washed with water (20 mL*2).Wash with saturated brine (20ml*1),After drying with anhydrous sodium sulfate,Desolvent, get crude,The crude product was purified by column chromatography to give a white solid.M.p. 83-85 C, yield: 88%.

The synthetic route of 6011-14-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Kaiai Network Technology Co., Ltd.; Xu Liyong; (6 pag.)CN108623518; (2018); 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. 17417-09-3, name is 2-Fluoro-5-nitrobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 17417-09-3

General procedure: To a partial solution of the diazeniumdiolate 3 or 14 (1 equiv) in DMSO (4 mL/mmol of diazeniumdiolate salt) was added the fluoro compound (4-8) (1 equiv) in THF (2 mL/mmol of fluoro compound) at room temperature. The resulting solution was stirred at room temperature overnight. To this homogeneous solution, water was added (8 mL/mmol of diazeniumdiolate), producing a yellow precipitate that was collected by filtration, washed with water, and dried. The crude product was purified by flash column chromatography or by recrystallization.

According to the analysis of related databases, 17417-09-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Nandurdikar, Rahul S.; MacIag, Anna E.; Holland, Ryan J.; Cao, Zhao; Shami, Paul J.; Anderson, Lucy M.; Keefer, Larry K.; Saavedra, Joseph E.; Bioorganic and Medicinal Chemistry; vol. 20; 9; (2012); p. 3094 – 3099;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 134604-07-2, 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. 134604-07-2 name is 1-Cyano-2-bromo-5-nitrobenzene, 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.

To a solution of isobutylboronic acid (5.89 g), 2-bromo-5-nitrobenzo nitrile (12.5 g) and Cs2C03 (35.9 g) in toluene (150 mL) and water (5 mL) stirred under nitrogen at room temperature was added solid PdCI2(dppf)- CH2CI2 adduct (2.248 g) in one charge. The reaction mixture was stirred at 100 C for 16 h. After cooling the reacion, the solvent was removed in vacuo. The residue was purified by column chromatography to give 2-(2-methylpropyl)-5-nitrobenzonitrile (D56) (11 g) as a light yellow oil. 5H (CDCI3, 400MHz): 1.00 (6H, d), 2.06 (1 H, m), 2.86 (2H, d), 7.52 (1 H, d), 8.37 (1 H, dd), 8.51 (1 H, d).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Cyano-2-bromo-5-nitrobenzene, and friends who are interested can also refer to it.

Reference:
Patent; GLAXO GROUP LIMITED; DENG, Guanghui; LIN, Xichen; REN, Feng; ZHAO, Baowei; WO2011/134280; (2011); A1;,
Nitrile – Wikipedia,
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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 56043-01-7 as follows. Safety of 2-Amino-6-methylbenzonitrile

Example 1: n-Propyl- (2-cyano-3-methyl-phenyl) sulfonamide 1.1 : 2-Cyano-3-methyl-phenylsulfonylchloride; A solution of 11.6 g (88 mmol) of 2-amino-6-methylbenzonitrile (prepared, e. g. accord- ing to WO 94/18980) in 120 ml of glacial acetic acid was initially charged and 32.2 g of concentrated hydrochloric acid were slowly added at room temperature. The reaction mixture was stirred at room temperatures for 10 minutes and then a solution of 6.4 g (92 mmol) of sodium nitrite in 20 ml of water was added dropwise at 5-10C. The reac- tion mixture was stirred at 0C for one hour to obtain the diazonium salt. In a separate stirred flask, a saturated solution of sulfur dioxide in glacial acetic acid was prepared at 10C and a solution of 5.5 g of copper ( . t) chloride in 11 ml of water was added. The reaction mixture of the diazonium salt which had been prepared beforehand was then added dropwise to the solution of the copper salt. The resulting mixture was stirred at room temperature for additional 45 minutes. Then the reaction mixture was poured into ice-cooled water and the aqueous phase was extracted three times with dichloro- methane. The combined organic layers were dried over a drying agent and filtered. The filtrate was concentrated in vacuo to afford 16.4 g (87% of the theory) of the title com- pound having a melting point of 75-77C.

According to the analysis of related databases, 56043-01-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; WO2005/35486; (2005); A1;,
Nitrile – Wikipedia,
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