Author: Jessica.F

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;,
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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;,
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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;,
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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;,
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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 115279-73-7 as follows. Safety of 1-(4-Aminophenyl)cyclopentanecarbonitrile

To a jacketed reactor were charged 71 (1.0 equiv), 10% Pd/C (7.0 wt %), and MeOH (10 vols). The contents of the reactor were inerted with N2 and then pressurized with H2 to 6.0 bar. The jacket was initially set to 18 C. to contain the minor exotherm that ensued. After 2 h, the jacket temperature was adjusted to 35 C. to achieve an acceptable reaction rate. The reaction mixture was stirred under these conditions overnight. HPLC analysis of an aliquot of the reaction mixture revealed that conversion to the intermediate aniline was complete (<0.1% of the hydroxylamine intermediate remaining) To the reactor were then charged AcOH (1.0 equiv), formaldehyde (37% solution in MeOH, 2.7 equiv), and 10% Pd/C (3.0 wt %). The reaction mixture was again inerted with N2 and then pressurized with H2 to 6.0 bar and heated to 45 C. (0160) After 2 h, HPLC analysis indicated that the reaction was complete (<0.1% monomethyl intermediate remaining) The reaction mixture was inerted with N2 and then filtered through Celite while still at 45 C. The reactor and cake were washed with additional MeOH (2.0 vols), and the resulting filtrate was transferred to a clean jacketed reactor vessel. The solution was then distilled down to a level of 10 vols while maintaining a pot temperature of 40-50 C. (jacket temperature 55 C., 250 torr). This led to a homogenous solution at the conclusion of the distillation. The solution was then cooled to 20 C. over 1 h. Crystallization began to occur at 33 C. Water (5.0 vols) was then added dropwise over 1 h while maintaining the batch temperature at 20 C. The resulting slurry was aged overnight and then filtered. The reactor and filter cake were washed with ice-cold 1:1 MeOH:H2O (5.0 vols). After drying under vacuum at 40-45 C. to constant weight, 72 was obtained in 90% yield with an HPLC purity of 96.0% (2.8% dimer-related impurity). According to the analysis of related databases, 115279-73-7, the application of this compound in the production field has become more and more popular. Reference:
Patent; Atterocor, Inc.; Hunt, III, Stephen Warren; Phillips, Martin Douglas; Matunas, Robert; Chen, Herman; Betancourt, Aimesther; Uzarama, Charles; Thibert, Roch; (31 pag.)US2016/90354; (2016); A1;,
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1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, 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. Application In Synthesis of 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile

Synthesis Example 3: Synthesis of 3,4,6-trichloro-5-(2,6-dibromo-phenoxy)-phthalonitrile 5 g of 3,4,5,6-tetrachlorophthalonitrile, 4.75 g of 2,6-dibromophenol, 3.9 g of K2CO3, and 25 ml of N,N-dimethyl formamide were put in a 100 ml flask and stirred while heated at 70° C. When the reaction was complete, EA (ethyl acetate) was used for an extraction. After the extraction, the resultant was concentrated to obtain a solid. The obtained solid was dissolved in a small amount of dichloromethane, several times washed with hexane, filtered, and vacuum-dried to obtain 3,4,6-trichloro-5-(2,6-dibromo-phenoxy)-phthalonitrile.

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMSUNG SDI CO., LTD.; JEONG, Euisoo; SEO, Hyewon; SHIN, Myoungyoup; SHIN, Sunwoong; JUNG, Juho; HAN, Gyuseok; (25 pag.)US2018/335547; (2018); A1;,
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