Month: January 2021

These common heterocyclic compound, 214623-57-1, name is 5-Amino-2-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. name: 5-Amino-2-methoxybenzonitrile

General procedure: A solution of 5-amino-2-alkoxybenzonitrile (20mmol), glacial acetic acid (50mL) and water (20mL) was added to the reaction flask at -10C under stirring, water-soluble sodium azide (30 mmol) was slowly added dropwise to the reaction mixture for 30 min, and the addition was completed,the reaction temperature is maintained steady 3h, extracted with dichloromethane, the organic layers combined, washed with brine, dried over anhydrous sodium sulfate , filtered, and concentrated to dryness under reduced pressure the crude product purified by column chromatography (ethyl acetate: petroleum ether = 1: 5) to give pure product.

The synthetic route of 5-Amino-2-methoxybenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHINA MEDICAL UNIVERSITY; MENG, FANHAO; ZHANG, TINGJIAN; WU, QINGXIA; WANG, LIN; SUN, QI; LIANG, JINGWEI; HE, XIN; (22 pag.)CN105294584; (2016); A;,
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Electric Literature of 26391-06-0, 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. 26391-06-0 name is 2-Cyano-N,N-diethylacetamide, 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.

Example 1 Preparation of N,N-diethyl-2-cyano-3-(-3-methoxy-4-hydroxy-5-nitrophenyl-)-acrylamide; (V) A suspension of 3-methoxy-4-hydroxy-5-nitro-benzaldehyde (100 g, 0.507 mol) in methanol (0.5 I) under nitrogen atmosphere at room temperature, is added with N,N-diethylamino-cyano-acetamide (142 g, 1.01 mol) and a sodium hydroxide solution (30.4 g, 0.761 mol) in methanol (0.5 1). The resulting mixture is reacted under mechanical stirring for 16 hours. After completion of the reaction, a 20% hydrochloric acid solution (0.5 I) is dropped in the mixture which is left to spontaneously cool to room temperature. The resulting product is filtered, washing with water (0.1 I for three times), then dried in the air. 155 g of product are obtained. Yield: 95%. 1H-NMR (300 MHz), delta (DMSO): 8.10 (d, 1 H); 7.85 (d, 1 H); 7.70 (s, 1 H); 3.40 (m, 4H); 1.15 (m, 6H).

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

Reference:
Patent; Dipharma Francis S.r.l.; EP1935873; (2008); A1;,
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Synthetic Route of 105-34-0, 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 105-34-0 as follows.

The mixture of benzaldehyde (0.5 mmol) and methyl cyanoacetate(0.5 mmol) in toluene 1 mL was incubated in the presence of Candida cylindracea lipase (30 mg) at 50 C for 4 days. The reaction was monitored by TLC analysis. After this time enzyme was filtered out and the solvent was evaporated in vacuo. The resulting residue was purified by column chromatography (silica gel, eluent ethyl acetate/hexanes) to obtain desired product 5a with 40% yield. 4.7. Characterization of obtained products 5a-u.4.7.1. Methyl (E)-2-cyano-3-phenylprop-2-enoate; (5a)White solid; melting point 89 C; 1H NMR (400 MHz, CDCl3) delta 8.20(s, 1H), 7.92 (dd, J=7.1, 1.5 Hz, 2H), 7.53-7.40 (m, 3H), 3.87 (s, 3H).13C NMR (100 MHz, CDCl3) delta 162.9, 155.3, 133.4, 131.4, 131.1, 129.3,115.4, 102.6, 53.4. All the resonances of 1H, 13C NMR spectra andmelting point were consistent with reported values [32]

According to the analysis of related databases, 105-34-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wilk, Monika; Trzepizur, Damian; Koszelewski, Dominik; Brodzka, Anna; Ostaszewski, Ryszard; Bioorganic Chemistry; vol. 93; (2019);,
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Synthetic Route of 1187-42-4,Some common heterocyclic compound, 1187-42-4, name is Diaminomaleonitrile, molecular formula is C4H4N4, 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 compound F (0.70 g, 1.46 mmol), diaminomaleonitrile (0.19 g, 1.76 mmol), 40 mL of ethanol, 40 mL of THF, and 0.23 mL of 12M hydrochloric acid were charged in a three-necked flask having a capacity of 300 mL, and the mixture was stirred while conducting heating at 40 C. for 24 hours. Water was added to the resultant solution, the resultant mixture was subjected to extraction with chloroform, and then the resultant extract was dried by adding sodium sulfate thereto. Sodium sulfate hydrate was removed by conducting filtration, and the solvent was distilled off from the filtrate using an evaporator. The resultant solid was purified by silica gel column chromatography (developing solvent: toluene) to obtain a red solid (yield amount: 0.52 g, yield: 64%).Chemical shift values (delta) of the compound measured by 1H NMR (400 MHz, CDCl3) were as follows: delta 9.16 (t, J=8.4 Hz, 2H), 8.76 (d, J=1.6 Hz, 1H), 8.70 (d, 8.4 Hz, 1H), 8.01 (dd, J=8.8 Hz, 2.0 Hz 1H), 7.96 (td, J=8.4 Hz, 1.2 Hz, 1H), 7.84 (td, J=8.4 Hz, 1.2 Hz, 1H), 7.66 (dt, J=8.8 Hz, 2.0 Hz 2H), 7.19-7.10 (m, 10H), 2.36 (s, 6H). It was confirmed by 1H NMR measurement that the obtained compound was a compound 2 (Da-CNBQx).

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

Reference:
Patent; KYUSHU UNIVERSITY, NATIONAL UNIVERSITY CORPORATION; Nippon Soda Co., Ltd.; YASUDA, Takuma; FURUE, Ryuhei; ISHIHARA, Hiroyuki; FUKUSHIMA, Yukio; (61 pag.)US2019/330162; (2019); A1;,
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Adding a certain compound to certain chemical reactions, such as: 1558-81-2, name is Ethyl 1-Cyano-1-cyclopropanecarboxylate, 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 1558-81-2, Formula: C7H9NO2

To a solution of ethyl 1 -cyanocyclopropanecarboxylate (1-127) (5 g, 36 mmol) in DME/MeOH (80 mL/8 mL) was added NaBH4 (10.65 g, 0.288 mol) in a portionwise manner at 0 ~ 5 C. The mixture was stirred at room temperature for 4 hr. TLC (petroleum ether: EtOAc=1 :1 ) showed the reaction was complete. The reaction mixture was diluted with saturated aq. NaHC03 (60 mL) and then extracted with 10% MeOH/CH2CI2 (8 x 100 mL). The combined organic layers were dried over Na2S04 and concentrated to give 1 -(hydroxymethyl)cyclopropanecarbonitrile (1-128) (3 g, 85%) as a light yellow oil, which was used without further purification.

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, Ethyl 1-Cyano-1-cyclopropanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; JOHNSON, Ted William; RICHARDSON, Paul Francis; COLLINS, Michael Raymond; RICHTER, Daniel Tyler; BURKE, Benjamin Joseph; GAJIWALA, Ketan; NINKOVIC, Sacha; LINTON, Maria Angelica; LE, Phuong Thi Quy; HOFFMAN, Jacqui Elizabeth; (335 pag.)WO2016/97918; (2016); A1;,
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Reference of 20925-27-3, 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. 20925-27-3 name is 4-Amino-2-chlorobenzonitrile, 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.

General procedure: In a typical experiment, a solution of sodium hydrogen carbonate (62.72 mmol) in 20 mL of water was stirred for 10 min and to it was added dichloromethane (20 mL) followed by substituted aniline (15.68 mmol). The reaction mixture was cooled to 0 C, thiophosgene (23.52 mmol) was introduced dropwise over a period of 30 min and continuously stirred at room temperature for 1 h. The reaction mixture was washed with brine solution; the organic layer was dried over anhydrous sodium sulphate and concentrated to get a crude gummy compound which was recrystalized in hexane under cold condition. The precipitate was filtered and dried to get the desired compound. The products were characterized by analytical and spectral methods.

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

Reference:
Article; Khatik, Gopal L.; Kaur, Jasmine; Kumar, Varun; Tikoo, Kulbhushan; Venugopalan; Nair, Vipin A.; European Journal of Medicinal Chemistry; vol. 46; 8; (2011); p. 3291 – 3301;,
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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 10406-25-4 as follows. HPLC of Formula: C8H8N2

(3) 0.1 g of intermediate C was added3, With the raw material0.1g in THF as a solvent at room temperature for 3h, the intermediate D-AWY113, yield 66%; specific reaction equation is as follows:

According to the analysis of related databases, 10406-25-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong University of Technology; Zhao, Suqing; Jiang, Zhengyun; Wu, Panpan; Zhang, Kun; Hong, Weiqian; Cui, Xiping; Chen, Yingshan; Hu, Qingqing; Jiao, Luoying; Xia, Nana; Chen, Ding; (21 pag.)CN106083742; (2016); A;,
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Synthetic Route of 10406-25-4, 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. 10406-25-4 name is 4-(Aminomethyl)benzonitrile, 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.

General procedure: A mixture of TBPB (1 mmol) and requisite aq NH3 or amine (1.1mmol) were charged in a round-bottom flask. The reaction mixture was stirred at r.t. for the indicated time, and progress of the reaction was monitored by TLC/GC. The crude product was directly purified by column chromatography (silica gel, 100-200 mesh, PE-EtOAc) to provide the desired pure product. The identity of the compound was confirmed by 1H NMR and 13C NMR spectroscopic methods.

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

Reference:
Article; Yadav, Dilip Kumar T.; Bhanage, Bhalchandra M.; Synlett; vol. 26; 13; (2015); p. 1862 – 1866;,
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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. 6136-68-1, name is 3-Acetylbenzonitrile, A new synthetic method of this compound is introduced below., Formula: C9H7NO

Part A. 3-(2-bromoacetyl) benzonitrile To a solution of 3-acetobenzonitrile (5 g, 0.0344 mol) in 45 ml glacial acetic acid was added pyridinium tribromide (11.3 g, 0.0355 mol). Reaction was stirred at room temperature under argon overnight. Reaction was then quenched with a saturated sodium sulfite solution (20 ml) and extracted with 3*25 ml dichloromethane. Combined organic phases were washed with 2*25 ml water, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude oil was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give 3-(2-bromoacetyl) benzonitrile (4.5 g, 58%) as a white solid. H1NMR (CDCl3) 4.371-4.403 (s, 2H); 7.613-7.664 (m, H); 7.838-7.888 (m, H); 8.192-8.261 (m, 2H)

The synthetic route of 6136-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cor Therapeutics, Inc.; US6399627; (2002); B1;,
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Related Products of 1735-53-1, 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. 1735-53-1, name is 4-Bromo-3-(trifluoromethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

Description for D29 2-(Trifluoromethyl)-4-biphenylcarboxylic acid (D29)The reaction was split into 4, using a quarter of the reagents in each: to a mixture of 4-bromo-3-(trifluoromethyl)benzonitrile (4 g, 16.00 mmol), phenylboronic acid (3.90 g, 32.0 mmol) and potassium carbonate (6.63 g, 48.0 mmol) in N,N-dimethylformamide (DMF) (64 ml) was added palladium tetrakistriphenylphosphine(O) (1.849 g, 1.600 mmol). Each reaction was heated in the microwave at 150 0C for 30 min. The combined reaction mixtures were filtered through celite, washed with ethyl acetate and the solvent removed in vacuo. The residue was partitioned between ethyl acetate (100 ml.) and water (100 ml.) and the organic phase washed with sodium bicarbonate solution (100 ml_). The organic phase was dried (MgSO4), filtered and the solvent removed in vacuo. The brown oil was triturated with dichloromethane and filtered to give a pale yellow solid, 2-(trifluoromethyl)-4-biphenylcarboxamide (2.47 g) which was used without further purification. To 2-(trifluoromethyl)-4- biphenylcarboxamide (2 g, 7.54 mmol) in ethanol (80 ml) was added potassium hydroxide (4.23 g, 75 mmol) and water and the mixture heated to 90 0C for 18 h. The reaction mixture was concentrated in vacuo and the residue partitioned between dichloromethane (100 ml.) and 2M HCI (100 ml_). The organic phase was isolated and dried (phase separator) and the solvent removed in vacuo to give the crude product. Purification using the Biotage Horizon, reverse phase cartridge, eluting 5- 100 % MeCN in water to give an off-white solid the title compound (960 mg) (N2123- 46-A5). MS (ES): C14H9F3O2 requires 266; found 265 (M-H+).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3-(trifluoromethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/74821; (2008); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts