Month: June 2021

Electric Literature of 94088-46-7,Some common heterocyclic compound, 94088-46-7, name is 2-Fluoro-6-methoxybenzonitrile, molecular formula is C8H6FNO, 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 A6.2 (228 g, crude) and 145 mL NH4OH in 1.0 L MeOH was added 30 g Raney Ni. The mixture was stirred in an autoclave at 40 oC under hydrogen atmosphere (25 atm) for 8 h. After filtration, the filtrate was concentrated under reduced pressure to get a pale yellow oil, which was purified by reduced pressure distillation to give the title compound (60 g, 54 %) as a colorless oil.1H NMR (500 MHz, DMSO-d6) delta ppm 1.58 (s, 2H), 3.67 (s, 1H), 6.75 (t, 1H), 6.82 (d, 1H), 7.22 (dd, 1H). LC- MS: [MH]+ = 156.1

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Fluoro-6-methoxybenzonitrile, its application will become more common.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue; ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (193 pag.)WO2017/221092; (2017); 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. 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8Cl4N2

3,4,5,6-tetrachlorophthalonitrile (5 g), isoamyl alcohol (5.9 g), 1,8-diazabicycloundec-7-ene (3.898 g), and tetrahydrofuran (50 ml) are in a 100 ml flask and then stirred while heated at 50° C. When a reaction is complete, an extraction is performed with EA (ethyl acetate). After the extraction, a liquid column-purified through column chromatography with EA/hexane is concentrated to obtain a solid, and the solid is vacuum-dried, obtaining a compound according to Synthesis Example 4.

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.; PAK, Chae Won; SEO, Hye Won; SHIN, Myoung Youp; JEONG, Eui Soo; CHOI, Seung Jib; (35 pag.)US2017/107224; (2017); A1;,
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Adding a certain compound to certain chemical reactions, such as: 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, 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 67515-59-7, COA of Formula: C8H3F4N

A mixture of 4-fluoro-3-trifluoro-methylbenzonitrile (Fluorochem 2223; 10 g; 52.8 mmol; 1 eq.) and morpholine (Fluka 69880; 9.25 ml 105.7 mmol; 2 eq.) was stirred at 600C for 8 hours. The mixture was cooled and diluted with water. The precipitate was filtered and dried to afford the title compound (12.9 g, 95%) as a white solid. HPLC (Method B) : Rt 3.61 min (purity 99.1 %). LC/MS : 257.1 (M+H)+. 1H NMR (CDCI3, 400MHz) delta 7.92 (1 H, s), 7.78-7.81 (1 H, d), 7.32-7.35 (1 H, d), 3.84-3.87 (4H, m), 3.04-3.06 (4H, m).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Fluoro-3-(trifluoromethyl)benzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MERCK SERONO S.A.; WO2009/43890; (2009); 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. 17216-62-5, name is Diethyl 2-(2-cyanoethyl)malonate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Diethyl 2-(2-cyanoethyl)malonate

(a) Diethyl 2-(2-cyanoethyl)-2-(5-nitropyrid-2-yl)malonate Sodium hydride (53% dispersion in oil) (30.71g, 0.66mole) was washed by decantation with xylene (2 * 150ml), ether (150ml), tetrahydrofuran (THF) (150ml) and finally suspended in THF (245ml). Diethyl 2-(2-cyanoethyl) malonate (156g. 0.73mole) in THF (80ml) was added dropwise over 1hr keeping the internal temperature at 18C to 22C (with ice bath cooling). The resulting suspension cleared over 15 minutes when 2-chloro-5-nitropyridine (88.3g, 0.55mole) was added to give a deep magenta solution. The resulting solution was refluxed for 1hr and the solvent was removed on the rotary evaporator. The resulting oil was partitioned between water (500ml) and chloroform (800ml), the pH was adjusted to ~7 (concentrated hydrochloric acid), and the chloroform was run off. The aqueous layer was extracted with a further (2 * 250ml) chloroform, the extracts were combined, dried over magnesium sulphate and the solvent was removed to give an amber oil (~245g). Ether (150ml) was added and the solution was allowed to crystallise to give the title compound (121.98g, 65%), m.p. 59.5-61C. (Found C, 53.7: H, 5.05; N, 12.35%. C15H17N3O6 requires C, 53.75; H, 5.1: N, 12.55%) NM, (CDCl3, 60 MHz); delta 1,37 (6H, t); 2.65 (4H, m); 4.26 (4H, q); 7.84 (1H, dd); 8,49 (1H, dd); 9.32 (1H, dd).

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 17216-62-5.

Reference:
Patent; SMITH KLINE & FRENCH LABORATORIES, LIMITED; EP287270; (1988); A1;,
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Application of 36282-26-5, 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 36282-26-5 as follows.

4-Fluoro-2-(5-(4-methoxybenzyl)-4,4-dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)benzonitrile. 2-Bromo-4-fluorobenzonitrile, tris(dibenzylideneacetone)dipalladium(0) (0.238 g, 0.26 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.231 g, 0.4 mmol) and potassium carbonate (5.72 g, 41.4 mmol) were stirred together. Added to this was a solution of 2-(4-methoxybenzyl)-3,3-dimethyl-1,2,5-thiadiazolidine 11-dioxide (8.00 g, 29.6 mmol) in dioxane (50 mL) and the resulting mixture stirred at 100 C. for 18 h. The cooled mixture was diluted with CH2Cl2 and the solids were removed by filtration. The solvent was evaporated leaving a yellow oil that was purified by flash chromatography (Biotage flash chromatography system, 5%-100% ethyl acetate/hexane) to give a cream colored solid that was triturated with ethyl acetate/hexane (1:4) to give the title compound as a white powder (4.6048 g, 42% yield). 1H NMR (500 MHz, CDCl3) delta: 7.71-7.65 (2H, m), 7.37 (2H, d, J=8.5 Hz), 7.12-7.08 (1H, m), 6.88 (2H, d, J=8.5 Hz), 4.28 (2H, s), 3.80 (3H, s), 3.78 (2H, s), 1.42 (6H, s).

According to the analysis of related databases, 36282-26-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/253677; (2009); A1;,
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Electric Literature of 53312-81-5, 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 53312-81-5 as follows.

General procedure: To the solution of carboxylic acid (1 eq.) in DCM were added HATU (1.05 eq.), amine (1.1 eq.) and DIPEA (2 eq.). The mixture was stirred for 16 h at room temperature. Afterwards, the solution was washed with water and brine. The resulting organic layer was dried over MgSO4, and the solvent was removed by evaporation. The crude material was purified by flash chromatography (CH2Cl2:MeOH).

According to the analysis of related databases, 53312-81-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Egyed, Attila; Bajusz, David; Keser?, Gyoergy M.; Bioorganic and Medicinal Chemistry; vol. 27; 8; (2019); p. 1497 – 1508;,
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Synthetic Route of 39095-25-5, 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. 39095-25-5, name is 2,5-Dimethylterephthalonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The 2,5-dimethylterephthalonitrile (1.560 g, 10.0 mmol) was precisely weighed with an analytical balance.Azobisisobutyronitrile (0.082 g, 0.5 mmol) and NBS (3.916 g, 22.0 mmol) were placed in a dry 250 mL single port round bottom flask.Then use a measuring cylinder to measure 100 mL of carbon tetrachloride and pour it into the flask.Put on the reflux condenser,Vacuum and protect with argonPlace the flask in an oil bath heated to 80C or more and stir vigorously.And using a flame gun to assist in the rapid reflux,After rapid reflux, the temperature of the reaction system was adjusted to 80 C. for 16 hours. After the reaction is completed,The reaction mixture was cooled to room temperature and filtered.After washing with CCl 4 (3×20 mL), the filtrate was concentrated under reduced pressure to a brown-red viscous oil.Add ethanol (20 mL) to dissolve it slightly by heating.Transfer to a beaker (100 mL) and wash the flask with ethanol (3 x 10 mL).Pour the lotion into the beakerAfter leaving at room temperature to a total volume of 10 mL or less, it was filtered to obtain a white powdery product.The crude product was subjected to silica gel column chromatography [eluent: v (n-hexane): v (ethyl acetate) = 12:1].White powder, yield 31.6% (0.98g),

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, 2,5-Dimethylterephthalonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zunyi Normal College; Huang Chibao; Zeng Boping; Liu Qibin; Zhang Daohai; (15 pag.)CN105085340; (2017); B;,
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Synthetic Route of 218632-01-0, The chemical industry reduces the impact on the environment during synthesis 218632-01-0, name is 3-Fluoro-4-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

3-((7-((benzyloxy)methyl)-3-(4-methoxybenzyl)-2-oxo-1-oxa-3-azaspiro[4.5]decan-7- yl)methyl)amino)-4-nitrobenzonitrile To a light yellow solution of 7-(aminomethyl)-7-((benzyloxy)methyl)-3-(4-methoxybenzyl)- 1-oxa-3-azaspiro[4.5]decan-2-one (4.27 g, 10.1 mmol) in MeCN (67.1 mL) was added potassium carbonate (2.78 g, 20.1 mmol) and 3-fluoro-4-nitrobenzonitrile (2.51 g, 15.1 mmol). the reaction was stirred at rt. After stirring 15 h, the reaction was filtered through a frit. The collected inorganics were washed with DCM/EtOAc. The filtrate was concentrated onto florisil and purified on a 80 g silica gel column (20 – 55 % EtOAc/hexanes, 30 min gradient; 55 % EtOAc/hexanes, 5 min.; 60 mL/min elution; 254 nm detection) to provide the title compound (5.02 g, 83 % yield) as a reddish-orange oil. MS (m/z) 571.0 (M+H+).

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, 3-Fluoro-4-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl; CHEUNG, Mui; EIDAM, Hilary, Schenck; GOODMAN, Krista, B.; HAMMOND, Marlys; HILFIKER, Mark, A.; PATTERSON, Jaclyn, R.; STOY, Patrick; YE, Guosen; WO2012/174342; (2012); 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. 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 33143-29-2

Generally, the reactions were performed using 0.3 mmol of substrate; 0.3 mmol of co-catalyst; 0.2 mmol of chlorobenzene (GC internal standard) and Jacobsen complex (15 mg, 0.024 mmol) as catalyst; in 4 mL of solvent with continuous stirring at the desired temperature. The oxidant (3 mmol) was added totally at the beginning of the reaction (slowly to prevent gas evolution) or progressively at a rate of 3 mmol h-1. The progress of the reaction was monitored by GC-FID, by removing small samples of the reaction mixture every 15 min. The relative proportions of compounds usually did not change from 30-45 min of reaction time, when oxidant was totally added at the beginning of the reaction or from 120-135 min when oxidant was progressively added to the reaction mixture.The epoxide stereoselectivity was determined by 1H NMR in comparison with published data for (-)-(1R,2S)-1,2-indene oxide [47,48] and (3R,4R)-6-cyan-2,2-dimethychromene [49] or by comparison of analytic standards for (R)-(+)-styrene oxide.

The synthetic route of 33143-29-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rocha, Mariana; Rebelo, Susana L.H.; Freire, Cristina; Applied Catalysis A: General; vol. 460-461; (2013); p. 116 – 123;,
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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. 3759-28-2, name is 2-(Cyanomethyl)benzonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H6N2

General procedure: Toa RB flask, 1-aryl/alkyl-3,3-bis-methylsulfanyl-propenone (1.0 mmol) and 2-cynomethyl-benzonitrile(1.0 mmol, 142.0 mg) was added. Then powderedKOH (2.0 mmol, 112.0 mg) and dry DMSO (5.0 mL) was added andreaction mixture was stirred for 2h at room temperature. Then reaction mixturewas quenched with ice-water and neutralized with 10% HCl and filtered. Crudewas purified by column chromatography using 15 % ethyl acetate in hexane as aneluent. All the compounds were characterized and reported earlier[1].

The synthetic route of 3759-28-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rai, Reeta; Dutta, Roshan Kumar; Singh, Surjeet; Yadav, Dharmendra Kumar; Kumari, Seema; Singh, Harpreet; Gupta, Rinkoo Devi; Pratap, Ramendra; Bioorganic and Medicinal Chemistry Letters; vol. 28; 9; (2018); p. 1574 – 1580;,
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