Month: June 2021

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. 950596-58-4, name is 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, A new synthetic method of this compound is introduced below., name: 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile

Example 1 : Preparation of Erlotinib HydrochlorideTo a solution of 2-amino-4,5-bis(2-methoxyethoxy)benzonitrile (5.0 g) in isopropanol (25.0 ml) was added drop-wise a solution of triethyl orthoformate (4.0 g); 3-ethnylphenylamine (3.45 g) and acetic acid (0.2 ml). The mixture was stirred and heated at reflux for 4 hours. The reaction progress was monitored by TLC. After completion of the reaction, the reaction mass was cooled to room temperature and the pH was adjusted to 3.0 to 4.0 with isopropanolic hydrochloride (3.0 ml). The reaction mixture was stirred for 2 hours at room temperature. The solid was filtered, washed with isopropyl alcohol and dried on the air oven to obtain the titleCompound.Yield: 3.0 g

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; RANBAXY LABORATORIES LIMITED; MURUGESAN, Balaguru; VEMPALI, Anandam; SATHYANARAYANA, Swargam; THAPER, Rajesh, Kumar; PRASAD, Mohan; WO2010/109443; (2010); 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. 5414-21-1, name is 5-Bromovaleronitrile, A new synthetic method of this compound is introduced below., Formula: C5H8BrN

Sodium hydride paste (6.16 g. of 61% w/w suspension in liquid paraffin) was added portionwise over 30 minutes to a solution of 3-nitropyrazole (17.4 g.) in dry DMF (150 ml.) with external ice cooling to maintain the temperature at 20-30. The mixture was stirred for 45 minutes and to the almost clear solution was added 5-bromovaleronitrile (25 g.) over 30 minutes, at 25-30, and the mixture was stirred for 4 hours. Water (450 ml.) and EtOAc (450 ml.) was added and the upper layer was separated, dried (MgSO4) and evaporated in vacuo to an oil which was a mixture of 5-(3-nitropyrazol-1-yl)valeronitrile and 5-(5-nitropyrazol-1-yl)valeronitrile. The oil was divided into two 15 g. portions which were fractionated on a silica column (3.5 cm diameter*100 cm long) eluted at 2 atmospheres by EtOAc/60-80 petroluem ether (3:7 v/v). The 1.5 isomer was eluted first followed by the 1:3 isomer. The 5-(3-nitropyrazol-1-yl)valeronitrile had m.p. 32-33. To a solution of 5-(3-nitropyrazol-1-yl)valeronitrile (9.16 g.) in dry tetrahydrofuran (200 ml.) was added 5% w/w palladium on carbon (1.8 g.). The mixture was stirred at 20 under an atmosphere of hydrogen. 3.2 Liters of hydrogen were absorbed over 4 hours. The catalyst was filtered off and the filtrate was evaporated in vacuo to give 5-(3-aminopyrazol-1-yl)valeronitrile as an oil.

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; Imperial Chemical Industries PLC; US4447441; (1984); 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. 501-00-8, name is 2-(3-Fluorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Quality Control of 2-(3-Fluorophenyl)acetonitrile

(0086) In a charge of 200 ml of methanol, 25.9 g (=0.1 mol) of aldehyde of the formula (II), where R1=-COOCH3, R4=-CH3 and R5 and R6=-CH3, and 13.5 g (=0.1 mol) of 3-fluorophenylacetonitrile were introduced. Subsequently, the pH was adjusted to around 10 with ca. 1 g of a 50% aqueous potassium hydroxide solution and the reactor contents were heated to a temperature of 60 C. and then stirred for ca. 6 hours. The mixture was then cooled to 25 C. and the reaction product isolated on a Nutsche filter. The filter cake was washed with ca. 50 ml of methanol and ca. 500 ml of water (T=90 C.). The washed product was dried in a vacuum drying cabinet at a temperature of 80 C. and a pressure of 200 mbar. (0087) Yield: 24.5 g (corresponds to 65% of theory), melting point 311 C.

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; LANXESS Deutschland GmbH; BORST, Hans-Ulrich; LINKE, Frank; MICHAELIS, Stefan; (10 pag.)US2017/349752; (2017); A1;,
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Related Products of 2469-99-0, 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. 2469-99-0 name is 3-Oxobutanenitrile, 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.

Porphyrin 16 (40mg, 0,026mmol) and 2-cyanoacetic acid 10 (10mg, 0.11mmol) were dissolved in a THF solution (5mL). Then, piperidine (8muL) was added and the reaction mixture was heated at 65C for 24 h under N2. The resulting solution was evaporated to dryness under vacuum. Finally, the crude residue was purified by column chromatography over silica gel using CH2Cl2/MeOH as an eluent (in a 98:2 ratio) to obtain ZnP-3DoH-CNCOOH in 78% yield (28mg). 1H NMR (500 MHz, CDCl3): delta=8.83 (d, J=3.7Hz, 2H), 8.78 (sb, 4H), 8.72 (d, J=4.2Hz, 2H), 8.24 (d, J=6.9Hz, 2H), 7.64 (m, 5H), 6.97 (m, 6H), 3.79 (m, 12H), 0.92 (m, 12H), 0.50 (m, 36H), 0.27 (m, 18H) ppm. MS (MALDI-TOF): calcd. for C84H102N5O8Zn [M + H]+ 1372.7020; found 1372.701. UV-Vis in THF [lambdamax/nm (epsilon/mM-1 cm-1)]: 422 (399.7), 550 (16.6).

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

Reference:
Article; Nikolaou, Vasilis; Charisiadis, Asterios; Chalkiadaki, Sofia; Alexandropoulos, Ioannis; Pradhan, Sourava C.; Soman, Suraj; Panda, Manas K.; Coutsolelos, Athanassios G.; Polyhedron; vol. 140; (2018); p. 9 – 18;,
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Synthetic Route of 6011-14-9, A common heterocyclic compound, 6011-14-9, name is 2-Aminoacetonitrile hydrochloride, molecular formula is C2H5ClN2, 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.

Toluene (5 mL)(2,3-b] pyrazin-7-yl) aniline (36 mg, 0.12 mmol) was added to a solution of 4- (2- (1-methyl-1H-pyrazol-4-yl) -5H-pyrrolo [Triphosgene (33 mg, 0.11 mmol)Add two drops of triethylamine,110 reflux reaction 5h,The reaction solution was cooled to room temperature,Aminoacetonitrile hydrochloride (28 mg, 0.30 mmol) was added,Triethylamine (100 mg, 0.10 mmol)Stirred at room temperature for 12 h,Reaction by adding silica gel, direct spin dry mix,Column separation (dichloromethane / methanol (v / v) = 15/1)35 mg of a white solid was obtained in a yield of 75.8%.

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

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Liu Bing; Huang Jiuzhong; Zheng Changchun; Zhang Yingjun; Ouyang Luo; Mao Hongfen; Nie Biao; Xu Juan; Chen Hongfen; (137 pag.)CN106336413; (2017); A;,
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Synthetic Route of 3759-28-2, 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. 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A mixture of 1-aryl/alkyl-3,3-bis-methylsulfanyl-propenone (1.0 mmol), 2-cyanomethyl-benzonitrile (1 mmol, 142.0 mg), and powdered KOH (2 mmol, 112.0 mg) in dry DMSO (5 mL) was stirred at room temperature for 2 h. Completion of reaction was monitored by TLC. After completion, reaction mixture was poured onto ice-water with constant stirring and then neutralized with 10% HCl. The precipitate obtained was filtered, washed with water and dried over dry sodium sulfate. Many compounds were purified by recrystallization in dry methanol. Some compounds were purified through column chromatography using 15% ethylacetate in hexane as an eluent. Characterization data for some of the synthesized compounds are reported earlier.17

The chemical industry reduces the impact on the environment during synthesis 2-(Cyanomethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Singh, Surjeet; Althagafi, Ismail; Yadav, Pratik; Panwar, Rahul; Kumar, Abhinav; Pratap, Ramendra; Tetrahedron; vol. 70; 46; (2014); p. 8879 – 8884;,
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Adding a certain compound to certain chemical reactions, such as: 53312-80-4, name is 4-Amino-2-fluorobenzonitrile, 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 53312-80-4, category: nitriles-buliding-blocks

Water (10 mL) was added to a single-necked flask, and then thiophosgene (1.27g) was added dropwise. After stirring at 25 C for 0.5 h under nitrogen protection, Compound 59-1 (1.00 g) was added in batches, and the resulting mixture further reacted at 25 C for 2 h. The reaction mixture was extracted with dichloromethane (10 mL×3). The organic phase was washed with saturated brine (15 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated. The residue obtained from the concentration was purified by column chromatography to obtain Compound 59-2. 1H NMR (400 MHz, CDCl3) delta ppm 7.63(dd, J=8.38, 7.06Hz, 1H), 7.10-7.15 (m, 1H), 7.07 (dd, J=9.15, 1.87Hz, 1H).

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, 4-Amino-2-fluorobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chia Tai Tianqing Pharmaceutical Group Co., Ltd.; Medshine Discovery Inc.; SHEN, Chunli; WU, Chengde; CHEN, Shenglin; CHEN, Shuhui; ZHANG, Xiquan; TIAN, Xin; (200 pag.)EP3666772; (2020); A1;,
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Electric Literature of 3556-60-3,Some common heterocyclic compound, 3556-60-3, name is 3-Methoxy-4-methylbenzonitrile, molecular formula is C9H9NO, 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.

To a solution of 3-methoxy-4-methylbenzonitrile (300 mg, 2.03 mmol) in 10 ml ethanol was added hydroxylammonium chloride (212 mg, 3.06 mmol) and triethylamine (268 mg, 2.65 mmol) and then the reaction mixture was stirred overnight at 50 C. After cooling to RT, the solvent was evaporated and the crude was solved in ethyl acetate and extracted with water and brine solution. The organic phase was dried over magnesium sulfate, filtered and evaporated under vacuum to yield the title compound (274 mg, 75 % of theory). LC-MS (method IB): RT = 0.33 min, m/z = 181 (M+H)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Methoxy-4-methylbenzonitrile, its application will become more common.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; ELLERMANN, Manuel; VALOT, Gaelle; CANCHO GRANDE, Yolanda; HAssFELD, Jorma; KINZEL, Tom; KOeBBERLING, Johannes; BEYER, Kristin; ROeHRIG, Susanne; SPERZEL, Michael; STAMPFUss, Jan; MEYER, Imke; KOeLLNBERGER, Maria; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; HEIERMANN, Joerg; HENGEVELD, Willem Jan; (764 pag.)WO2016/71216; (2016); A1;,
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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. 66389-80-8, name is tert-Butyl 4-cyanobenzylcarbamate, This compound has unique chemical properties. The synthetic route is as follows., name: tert-Butyl 4-cyanobenzylcarbamate

130 g (0.56 mol) of product 3a, 58.4 g (0.84 mol) of hydroxylamine×HCl and 146 ml of DIEA were dissolved in 1.5 l of methanol. The mixture was boiled under reflux for 6 h and then stirred at room temperature overnight. The solvent was removed in vacuo, and the oily residue was dissolved in 1.5 l of acetic acid, mixed with 160 ml (1.68 mol) of acetic anhydride and stirred for 30 min. The solvent was removed in vacuo, and the residue was taken up with ethyl acetate and washed 3× with NaCl-saturated water and then dried over Na2SO4. The solvent was removed as far as possible in vacuo, and the product was crystallized from ethyl acetate. Yield: 110.6 g (0.36 mol) of crystalline solid, HPLC: 39.76% B

According to the analysis of related databases, 66389-80-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Stuerzebecher, Joerg; Steinmetzer, Torsten; Schweinitz, Andrea; Sturzebecher, Anne; Donnecke, Daniel; US2007/66539; (2007); 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 21423-81-4 as follows. Computed Properties of C8H6ClN

3-chloro-4-methylbenzonitrile (2 g, 13.2 mmol) was dissolved in carbon tetrachloride (20 ml), and N-bromosuccinimide (3.5 g, 19.8 mmol) and 2,2-azo-bis-isobutyronitrile (216 mg, 1.32 mmol) were added thereto, followed by stirring at room temperature for 12 hours. After completion of the reaction, the organic layer was separated using CH2Cl2 and H2O, and the separated organic layer was dried with MgSO4 and filtered. The filtrate was subjected to column chromatography (EA/n-Hex = 1:9), thereby obtaining 2-chloro-4-cyanobenzyl bromide (1.2 g, 5.2 mmol, 40 %).[1699] 1H NMR (400 MHz, CDCl3) delta 7.72 (s, 2H), 7.28 (s, 1H), 4.59 (s, 2H).

According to the analysis of related databases, 21423-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HYUNDAI PHARM CO., LTD.; LEE, In Hee; PARK, Chang Min; KIM, Se Hoan; CHAE, Hee Il; PYEON, Doo Hyeok; SHIN, Myoung Hyeon; HWANG, Jeong Un; MOON, Soon Young; HA, Tae Young; KIM, So Youn; CHOI, Hyuk Joon; YOO, Myoung Hyun; LEE, Jong Chan; KIM, Young Seok; RHEE, Jae Keol; WO2012/128582; (2012); A2;,
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