Tag: M.W=100-200

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 2042-37-7 as follows. HPLC of Formula: C7H4BrN

General procedure: In 50 mL round bottom flask, aryl halide (1.0 mmol), pyrazole (1.2 mmol), ligand (0.04 mmol), Cu2O (0.10 mmol), cesium carbonate (2.0 mmol), and dry solvent (20 mL) were placed under nitrogen atmosphere. The reaction mixture was heated in oil bath up to specified temperature under constant stirring for 20 h and then allowed to cool to room temperature. The reaction mixture was filtered through a plug of Celite in a fritted filter funnel and washed with ethyl acetate. If DMSO is used as solvent, it is extracted by washing the filtrate with 25 mL water for three times. The organic phase was dried over anhydrous MgSO4 and was removed under reduced pressure to provide the crude product which was purified by column chromatography on silica gel, using hexane and ethyl acetate in 3:1 ratio, respectively, as an eluent.

According to the analysis of related databases, 2042-37-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Damkaci, Fehmi; Alawaed, Abdulkhaliq; Vik, Erik; Tetrahedron Letters; vol. 57; 20; (2016); p. 2197 – 2200;,
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Electric Literature of 654-70-6, 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. 654-70-6 name is 4-Cyano-3-trifluoromethylaniline, 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.

1) Preparation of 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile (1.1) Compound 1.1 can be prepared by process “A”. To this end, 14.74 g (79.21 mmol) of 4-amino-2-trifluoromethylbenzonitrile were dissolved in 200 ml of dry acetonitrile. This solution was added dropwise with stirring to a 20% solution, heated to 70 C., of phosgene in toluene and then stirred for 1 h. The cooled reaction solution was concentrated under reduced pressure, and the residue was taken up with toluene and concentrated again under reduced pressure. Finally, the residue was dissolved in 150 ml of dry acetonitrile and the solution was admixed with 15.5 g (79.21 mmol) of tert-butyl 2-amino-2-methylpropionate hydrochloride with stirring. 12.02 g (118.8 mmol) of triethylamine were slowly added dropwise to the reaction mixture which was then stirred at room temperature for 45 min. Thereafter, the mixture was admixed cautiously with 50 ml of concentrated hydrochloric acid and stirred at 70 C. for 1 h. The cooled reaction mixture was concentrated under reduced pressure and the residue was admixed with ethyl acetate and water. The organic phase was removed, washed with saturated sodium carbonate solution and then with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel with 2:1 heptane/ethyl acetate. 21.2 g (90% yield) of 4-(4,4-dimethyl-2,5-dioxoimidazolidin-1-yl)-2-trifluoromethylbenzonitrile 1.1 with the melting point of 208-211 C. were obtained. ; 1) Preparation of 4-(2,4-dioxo-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrile (28.1) Compound 28.1 can be prepared by process “A”. To this end, 5.3 ml of phosgene solution (20% in toluene) were initially charged under argon atmosphere. At 75 C., a solution of 4-cyano-3-trifluoromethylaniline in 15 ml of dry acetonitrile was slowly added dropwise. After the addition had ended, the mixture was stirred at 75 C. for another 90 min. The mixture was concentrated under reduced pressure. The residue was then taken up repeatedly in toluene and concentrated again under reduced pressure. Finally, the residue was dissolved in 15 ml of dry tetrahydrofuran, admixed with 0.72 g of 1-amino-1-cyclohexanecarboxylic acid and dropwise with 1.05 ml of triethylamine, and the mixture was stirred at room temperature for 2 h. After standing overnight at room temperature, the reaction mixture was admixed with 5 ml of concentrated hydrochloric acid and stirred under reflux for 2 h. The cooled reaction mixture was admixed with saturated sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure. 0.62 g of 4-(2,4-dioxo-1,3-diazaspiro[4.5]dec-3-yl)-2-trifluoromethylbenzonitrile (28.1) was obtained. 1H NMR: 9.21, s, 1H, 8.30, d, 1H, 8.19, s, 1H, 8.02, d, 1H, 1.8-1.5, m, 9H, 1.4-1.25, m, 1H.

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

Reference:
Patent; SANOFI-AVENTIS; US2009/215728; (2009); 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. 64248-64-2, name is 2,5-Difluorobenzonitrile, A new synthetic method of this compound is introduced below., Computed Properties of C7H3F2N

26.1 4-(2-Cyano-4-fluoro-phenoxy)-piperidine-1-carboxylic acid tert-butyl ester The title compound was prepared a follows. 2-5-Difluorobenzonitrile (1.00 g, 7.2 mmol) was added at room temperature to a stirred mixture under argon of sodium hydride (55%, 207 mg, 9 mmol) in dimethylformamide (DMF) (10 ml). 4-Hydroxypiperidine-1-carboxylic acid tert-butyl ester (3.32 g, 17 mmol) was added in portions. The resulting mixture was stirred several hours at 50 C. before partitioning it between H2O and ethyl acetate (EtOAc). The organic layer was washed with sat. aq. NH4Cl sol. and brine and dried over MgSO4. Evaporation of the solvent yielded 2.24 g (97.2%, 7 mmol) of a light brown solid. MS (m/z): 321.1 (M+H+).

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; Gobbi, Luca Claudio; Jaeschke, Georg; Roche, Olivier; Rodriguez Sarmiento, Rosa Maria; Steward, Lucinda; US2008/103174; (2008); 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. 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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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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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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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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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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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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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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