Month: July 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. 198203-94-0, name is 2-Fluoro-3-methoxybenzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 2-Fluoro-3-methoxybenzonitrile

2- fluoro-3-methoxybenzonitrile (500 mg, 3.31 mmol) was dissolved in methanol (40 mL). This solution was cooled to 0 C. Nickel (II) chloride hexahydrate (79 mg, 0.33 mmol) and di-tertbutyl dicarbonate (1.44g, 6.62mmol) were added followed by sodium borohydride (876 mg, 23.16 mmol) portionwise. The reaction mixture was stirred, allowed to warm to rt and stirred for 3 days. The MeOH was removed in vacuo. The residue was dissolved in CHCI3 (150 mL), washed with sat NaHC03 (aq) (50 mL), water (50mL), brine (50mL), dried (Na2S04) and evaporated in vacuo. The residue was purified by chromatography (silica), eluent 20% EtOAc / 80% Pet. Ether, to give a white solid identified as (2-fluoro-3-methoxybenzyl)-carbamic acid tert-butyl ester (540 mg, 0.2 mmol, 64% yield). [MH]+ = 255.8

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; KALVISTA PHARMACEUTICALS LIMITED; DAVIE, Rebecca Louise; EDWARDS, Hannah Joy; EVANS, David Michael; HODGSON, Simon Teanby; PETHEN, Stephen John; ROOKER, David Philip; (139 pag.)WO2017/207983; (2017); 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. 25808-30-4, name is 2-(Methylamino)acetonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 25808-30-4

In a vessel load: 120 g of nitrobenzene and 53.3 g of aluminium chloride making attention to the exothermic effect, then 21.2 g of methylaminoacetonitrile hydrochloride were added. Then 27.1 g of veratrole and 0.6 g of anisole were poured into the mixture. In a few minutes a homogeneous solution was obtained, then hydrochloric acid was bubbled through the solution vigorously for 6 hrs at a temperature of 25° C.The mixture was then poured into 320 ml of water under cooling. Then the organic layer was separated at 75° C. and the aqueous layer underwent to vacuum distillation (50 ml are distilled off) in order to remove the latest traces of solvent. The obtained aqueous layer was then treated with 4.9 g of decolorizing charcoal for 1 hr at 80° C. Then the charcoal was filtered off and the panel washed with 50 ml of water which were joined together with the mother liqueur.

According to the analysis of related databases, 25808-30-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ALBANI, Davide; Arosio, Roberto; Merli, Valeriano; US2009/171110; (2009); A1;,
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Reference of 42872-83-3,Some common heterocyclic compound, 42872-83-3, name is 2-Bromo-5-methylbenzonitrile, molecular formula is C8H6BrN, 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 mixture of 2-Bromobenzonitrile (183.4 mg, 1 mmol), benzaldehyde (210.5 mg, 2 mmol),CuCl2 (17.2 mg, 0.1 mmol), Cs2CO3 (652.2 mg, 2 mmol), and L-proline (23.2 mg, 0.2 mmol) in H2O(2 mL) was added 27% aqueous ammonia (1 mL) in a tube under air atmosphere. Then the tubewas sealed, and the mixture was stirred at 100 C for 12 h. Next, the tube was opened to air and themixture was stirred at 100 C for another 12 h. After being cooled to room temperature, the resultingmixture was quenched with NH4Cl solution and extracted with ethyl acetate. The combined organiclayer was washed with brine, and then dried over anhydrous Na2SO4. The solvent was evaporatedunder reduced pressure and the crude product was purified by chromatography on silica-gel to afford2-phenylquinazolin-4(3H)-one (4aa) in 75% isolated yield.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-methylbenzonitrile, its application will become more common.

Reference:
Article; Liu, Zibin; Zeng, Li-Yan; Li, Chao; Yang, Fubiao; Qiu, Fensheng; Liu, Shuwen; Xi, Baomin; Molecules; vol. 23; 9; (2018);,
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Reference of 123-06-8, 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. 123-06-8, name is Ethoxymethylenemalononitrile, This compound has unique chemical properties. The synthetic route is as follows.

Example 5A8.7 g (53.5 mmol) of 4-fluorphenylhydrazine hydrochloride was suspended with 6.5 g (53.5 mmol) of ethoxymethylenemalononithle in 13 ml of ethanol, and 22.2 ml (160 mmol) of thethylamine were added. The reaction mixture was heated to 500C for 2 h. After cooling to room temperature the solvent was removed under reduced pressure. The remaining residue was treated with water (25 ml) and extracted three times with ethyl acetate. The organic layer was dried over sodium sulphate, filtered and the filtrate was concentrated under reduced pressure. The remaining residue was purified by preparative MPLC (SiO2, eluent CH2CI2). 5.0 g (46% of theory) of the product were obtained as an oil, that solidifies over night.LC-MS (Method 1 ): RT = 1.06 minMS (ESI pos): m/z = 203 (M+H)+.

The chemical industry reduces the impact on the environment during synthesis Ethoxymethylenemalononitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/68617; (2009); A1;,
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Electric Literature of 5332-06-9, A common heterocyclic compound, 5332-06-9, name is 4-Bromobutanenitrile, molecular formula is C4H6BrN, 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.

Reference Example 34-(benzylamino)butanenitrileBenzylamine (5.02 mL, 46 mmol) and calcium carbonate (23.65 g, 171.12 mmol) dissolved in anhydrous acetonitrile (115 mL) were stirred for 10 minutes at room temperature. After adding 4-bromonitrile (4.78 mL, 48.3 mmol), reaction was carried out at 100 C. for 2 days. A target compound (6.69 g, 38.395 mmol, 83.5%) was yielded as liquid by separating the reaction mixture in the same manner as Reference Example 1.1H NMR (CDCl3, 300 MHz) delta 7.37-7.29 (m, 5H), 3.79 (s, 2H), 2.77 (t, J=6.6 Hz, 2H), 2.48 (t, J=7.1 Hz, 2H), 1.88-1.79 (m, 2H).

The synthetic route of 5332-06-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Institute of Science and Technology; US2011/319619; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 62088-13-5, name is Ethyl 3-(3-cyanophenyl)-3-oxopropanoate, 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 62088-13-5, Application In Synthesis of Ethyl 3-(3-cyanophenyl)-3-oxopropanoate

Example K9 {2-[3-(3-Cyano-phenyl)-3-oxo-propionylamino]-4-furan-3-yl-phenyl}-carbamic Acid tert.-Butyl Ester Prepared from (2-amino-4-furan-3-yl-phenyl)-carbamic acid tert.-butyl ester (Example G11) and 3-(3-cyano-phenyl)-3-oxo-propionic acid ethyl ester (Pol. J. Chem. 1978, 25) according to the general procedure K. Obtained as an orange solid (460 mg). MS (ISP) 446 [(M+H)+], 463 [(M+NH4)+] and 468 [(M+Na)+]

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Hoffmann-La Roche Inc.; US6509328; (2003); B1;,
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Related Products of 38469-84-0, 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. 38469-84-0 name is 5-Methoxy-2-nitrobenzonitrile, 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.

Step 3 2-Amino-5-methoxybenzonitrile A 100 mL round bottom flask was charged with 5-methoxy-2-nitrobenzonitrile (1.7 g, 9.55 mmol), sodium dithionite (4.99 g, 29 mmol), water (15 mL) and EtOH (50 mL). The resulting mixture was heated at reflux for 1 h. Work-up: the reaction mixture was concentrated in vacuo to remove ethanol then extracted with EtOAc (50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo, to afford 1.4 g (quantitative) of the product as yellow oil. It was used in the next step without further purification.

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

Reference:
Patent; Kalypsys, Inc.; Alcon Research, Ltd; US2010/120741; (2010); A1;,
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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. 623-26-7, name is Terephthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Terephthalonitrile

EXAMPLE 2 Hydrogenation of Terephthalonitrile Into a 100-ml autoclave, were charged 3.2 g of terephthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5% by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 94.8 mol%, the yield of 4-cyanobenzylamine was 88.8 mol% and the yield of p-xylynenediamine was 5.8 mol%. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of Ni-diatomaceous earth pellets (manufactured by Nikki Chemical Co., Ltd.; Ni supported amount = 46% by weight). The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 100 mol%, the yield of 4-cyanobenzylamine was 0.5 mol% and the yield of p-xylynenediamine was 87.7 mol%. EXAMPLE 5 Hydrogenation of Terephthalonitrile Into a 100-ml autoclave, were charged 3.2 g of terephthalonitrile, 10.4 g of mesitylene, 10.0 g of liquid ammonia and 2.0 g of Pd-alumina pellets (manufactured by N.E. Chemcat Corporation; Pd content = 5% by weight), and the inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 94.8 mol%, the yield of 4-cyanobenzylamine was 88.8 mol% and the yield of p-xylynenediamine was 5.8 mol%. The reaction solution separated from the catalyst was charged into a 100-ml autoclave together with 10.0 g of liquid ammonia and 2.0 g of the catalyst A. The inner pressure was raised to 4.9 MPa by hydrogen gas. Then, the autoclave was shaken at 50C until the change of pressure was no longer appreciated. The analysis on the reaction product solution showed that the conversion of terephthalonitrile was 100 mol%, the yield of 4-cyanobenzylamine was 0.2 mol% and the yield of p-xylynenediamine was 92.1 mol%.

The synthetic route of 623-26-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITSUBISHI GAS CHEMICAL COMPANY, INC.; EP1449825; (2004); 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. 1735-88-2, name is 2-Cyano-N-(4-fluorophenyl)acetamide, A new synthetic method of this compound is introduced below., COA of Formula: C9H7FN2O

The compound prepared in step 1 (480 mg, 3.93 mmol) and the compound prepared in step 2 (538 mg, 3.02 mmol) were dissolved in N, N-dimethylformamide, and then piperidine (0.06 mL, 0.60 mmol) ) And acetic acid (0.23 mL, 3.93 mmol) were added sequentially, followed by stirring at 135 C. for 12 hours. After cooling to room temperature, extracted with ethyl acetate, the separated organic layer was dried over anhydrous sodium sulfate, and the residue obtained by concentrating the solvent under reduced pressure was purified by column chromatography to obtain the title compound (411 mg, yield: 56%, orange solid).

The synthetic route of 1735-88-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Welmakeo Bio Co., Ltd.; Lee Hyeon-ho; Park Jun-ho; Huh Seon-cheol; Moon Jae-hui; Shin Jae-sik; Hong Seung-u; Park Yun-seon; Kim Yo-sep; Lee So-hui; Kim Hyo-jin; Park Hye-bin; (48 pag.)KR2019/106802; (2019); A;,
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Related Products of 127946-77-4, 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. 127946-77-4, name is 1-Amino-1-cyclopropanecarbonitrile hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: N-protected amino acid was dissolved in dichloromethane (DCM). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl, 1.3 eq.) and hydroxybenzotriazole (HOBt ·xH2O, 1.3 eq.) were added at 0 C and the mixture was stirred for 50 min, after which thecorresponding amine (1.3 eq.) and N,N-Diisopropylethylamine (DIPEA, 1.3 eq.) were added at 0C. After stirring overnight, the mixture was washed with a 5% potassium sulfate solution(KHSO4), a 5% sodium bicarbonate solution (NaHCO3) and with water. After drying over sodiumsulfate (Na2SO4) and evaporation of the solvent, the residue was purified via columnchromatography.

The chemical industry reduces the impact on the environment during synthesis 1-Amino-1-cyclopropanecarbonitrile hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Silva, Daniel G.; Ribeiro, Jean F.R.; De Vita, Daniela; Cianni, Lorenzo; Franco, Caio Haddad; Freitas-Junior, Lucio H.; Moraes, Carolina Borsoi; Rocha, Josmar R.; Burtoloso, Antonio C.B.; Kenny, Peter W.; Leitao, Andrei; Montanari, Carlos A.; Bioorganic and Medicinal Chemistry Letters; vol. 27; 22; (2017); p. 5031 – 5035;,
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