Category: nitriles-buliding-blocks

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. category: nitriles-buliding-blocks

General procedure: To a solution of DAMN (0.54 g, 0.5 mmol) in acetonitrile (5 mL), the appropriate aromatic aldehyde (0.5 mmol) and CAN (5 molpercent) were added. The reaction mixture was stirred at room temperature for 1?3 min. Then, 5 mL acetonitrile and 40 molpercent of CAN were added again and the reaction mixture stirred at 50 °C for the desired time (Table 3). After completion of the reaction (reaction progress was monitored by TLC, ethyl acetate/n-hexane, 2:1), acetonitrile solvent was removed from the reaction mixture, and, by increasing the minimum ethanol and water, a precipitate was formed which was filtered and washed with cold water and ethanol. The product obtained in this way was pure.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1187-42-4, its application will become more common.

Reference:
Article; Kalhor, Mehdi; Seyedzade, Zahra; Research on Chemical Intermediates; vol. 43; 5; (2017); p. 3349 – 3360;,
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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. 21803-75-8, name is 4-Amino-3-chlorobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Amino-3-chlorobenzonitrile

Step 8 – Synthesis of Compound 6; To a stirred solution of sodium hydride (0.08 g, 0.2.07 mmol) in tetrahydrofuran (6 ml) in a sealed tube was added a solution of 4-amino-3-chloro benzonitrile (0.06 g, 0.42 itimo.) in tetrahydrofuran (9 mL) and the resulting reaction was allowed to stir for about 45 minutes. The reaction mixture was then cooled to 00C and a solution of compound IJ (0.15 g. 0.41 mmol) in tetrahydrofuran (9 mL) was added and the resulting reaction was heated to reflux and allowed to stir at this temperature for about 15 hours. The reaction was cooled to room temperature, quenched with water and extracted 2 times with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered, concentrated in vacuo. The resulting residue was purified using preparative thin layer chromatography (hexane/acetone (80/20)) to provide compound 6 (0.12 g, 60.13%). 6

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; SCHERING CORPORATION; NEELAMKAVIL, Santhosh, Francis; BOYLE, Craig D.; NEUSTADT, Bernard, R.; CHACKALAMANNIL, Samuel; GREENLEE, William, J.; WO2010/9208; (2010); A1;,
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Application of 5332-06-9, 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 5332-06-9 as follows.

General procedure: To a stirred solution of N-norhydromorphone (S10 in the SupplementaryMaterials, 0.406 g, 1.5 mmol) in DMF (10 mL) were added NaHCO3 (0.504 g, 6 mmol) and 1-(2-bromoethyl)-4-chlorobenzene (0.480 mL, 3.3 mmol). The mixture was heated at 90 C overnight,cooled to room temperature, filtered through Celite, and concentrated in vacuo. Water (10 mL) wasadded and the mixture extracted with CHCl3 (3 × 20 mL). The combined organics were washed withH2O (5 × 20 mL), dried over Na2SO4, filtered through Celite, and concentrated in vacuo to afford 2ifree base as a crude colorless oil. Purification of this oil by SiO2 column chromatography with 10%NH4OH in MeOH/CHCl3 (gradient, 0 ? 4% of 10% NH4OH) afforded 2i (0.420 g, 70%) as a colorlessoil.

According to the analysis of related databases, 5332-06-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Adler, Martin W.; Bergman, Jack; Chadderdon, Aaron M.; Crowley, Rachel Saylor; Geller, Ellen B.; Hanna, Ramsey D.; Hassan, Sergio A.; Herdman, Christine A.; Inan, Saadet; Irvin, Thomas C.; Jacobson, Arthur E.; Kaska, Sophia; Katz, Jonathan L.; Kopajtic, Theresa A.; Lee, Yong-Sok; Paronis, Carol A.; Prisinzano, Thomas E.; Rice, Kenner C.; Traynor, John R.; Wang, Meining; Withey, Sarah L.; Molecules; vol. 25; 11; (2020);,
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Some common heterocyclic compound, 4107-65-7, name is 2,4-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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. category: nitriles-buliding-blocks

Step a 2,4-dimethoxybenzonitrile (2 g) was mixed with pyridinium chloride (5.67 g) and the reaction mixture was fused at 210 C. for 2 hours. After being left to stand at room temperature overnight, the mixture was diluted with water and extracted into diethyl ether. The ether extracts were washed with water, dried over magnesium sulphate and concentrated to give a pink solid which was washed with petrol and air dried to give 2,4-dihydroxybenzonitrile (1.17 g) (m pt 176-178 C.).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4107-65-7, its application will become more common.

Reference:
Patent; Imperial Chemical Industries plc; US5120869; (1992); A;,
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Related Products of 31603-77-7, 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. 31603-77-7, name is 4-Biphenylacetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-([1,1′-biphenyl]-4-yl) acetonitrile I (e.g. Sigma-Aldrich, catalogue no.133612, CAS no. 31603-77-7) (100 g, 517.46 mmol) in ethylene glycol (1000 mL), a solution of potassium hydroxide (590 g, 10515 mmol) in water (1000 mL) was added and the resulting mixture was heated to 120 C and stirred for 16h. The reaction mixture was cooled to 0 C and acidified with concentrated HCI with stirring. The solid separated out wascollected by filtration, washed with water and dried. The solid was dissolved in ethyl acetate and the ethyl acetate layer was washed with water, dried over sodium sulfate and concentrated under reduced pressure to get white solid. The solid was taken in petroleum ether, stirred for -30 mm, filtered and dried to get 2-([i,i-biphenyl]-4-yl)acetic acid 2 as white solid. (107.2 g, 97.6%).1H-NMR (400 MHz, DMSO-d6): 3 12.41 (br. s, 1 H), 7.59-7.66 (m, 4 H), 7.44-7.47 (m, 2 H);7.34-7.37 (m, 3 H), 3.61 (5, 2 H) ppm; MS (MM-ES, APCI): negative mode 257.0 [M +HCO2f.

The synthetic route of 4-Biphenylacetonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; KLEINBECK-RINIKER, Florian Karl; MARTIN, Benjamin; PENN, Gerhard; VENTURONI, Francesco; SCHLAMA, Thierry; RUCH, Thomas; ALLMENDINGER, Thomas; WIETFELD, Bernhard; FILIPPONI, Paolo; (104 pag.)WO2017/98430; (2017); 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. 38487-85-3, name is 2-Amino-4-methoxybenzonitrile, A new synthetic method of this compound is introduced below., name: 2-Amino-4-methoxybenzonitrile

To a stirred solution of 2-amino-4-methoxy benzonitrile (19.4 g, 131 mmol) in acetonitrile (582 mL) was added NBS (18.66 g, 104 mmol) and the mixture was stirred for 1 h at 0 C. The reaction was quenched by addition of ice. The volatiles were concentrated under reduced pressure and the residue was extracted with ethylacetate (2 x 200 mL). The combined organic layers were washed with brine solution (200 mL), dried over sodium sulfate and concentrated under reduced pressure to afford 2-amino-5-bromo-4-methoxy benzonitrile (26 g, 114 mmol, 87% yield) as a brown solid. LCMS (ESI) m/e 227.6 (bromo pattern) [(M+H), calcd for C8H8BrN2O, 227.06]; LC/MS retention time (method C): ti = 1.46 mm.

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; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; MACOR, John E.; BRONSON, Joanne J.; DASGUPTA, Bireshwar; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; (226 pag.)WO2016/53794; (2016); A1;,
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Electric Literature of 20249-16-5, 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. 20249-16-5, name is 3-Oxocyclobutanecarbonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 59A 3,3-Difluorocyclobutanecarbonitrile Under argon, 14.57 g (153.2 mmol) of 3-oxocyclobutanecarbonitrile from Example 58A were initially charged in 200 ml of absolute dichloromethane, 40.48 ml (306.4 mmol) of diethylaminosulphur trifluoride dissolved in 50 ml of dichloromethane were added at 0 C. and the mixture was stirred at RT overnight. A little at a time, the reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, cooled to 0 C., and stirred for 30 minutes. The organic phase was separated off and the aqueous phase was extracted with 200 ml of dichloromethane. The combined organic phases were twice washed with water, dried over sodium sulphate, filtered and concentrated. This gave 15.2 g (85% of theory) of the title compound. GC-MS (Method H): Rt=1.43 min MS (ESpos): m/z=98 (M-F)+

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-Oxocyclobutanecarbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; VAKALOPOULOS, Alexandros; VALOT, Gaelle; FOLLMANN, Markus; WUNDER, Frank; STASCH, Johannes-Peter; MARQUARDT, Tobias; DIETZ, Lisa; LI, Volkhart Min-Jian; RAY, Nicholas Charles; BACHERA, Dominika; (71 pag.)US2017/50961; (2017); 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 179897-89-3 as follows. Recommanded Product: 179897-89-3

To a mixture of 5-bromo-2-fluorobenzonitrile (1.00 g, 5.00 mmol), (4- fluorophenyl)boronic acid (0.70 g, 5.00 mmol), and K2CO3 (2.073 g, 15.00 mmol) in 1,4- dioxane (12.0 mL) and water (4.0 mL) was added PdCl2(dppf) (10 mg, 0.014 mmol). After degassing with nitrogen for 2 min, the vial was capped and the reaction mixture was heated in a Biotage Initiator microwave reactor to 140 0C for 30 min. An identical reaction on the same scale was run in a separate vial and the crude reaction mixtures were combined. The combined reaction mixtures were diluted with EtOAc (50 mL) and washed with water (50 mL) and brine (2 x 50 mL). The organic layer was filtered through a pad of silica gel and washed through with EtOAc. Isolute Si-TMT (~ 0.5 g) was added and the mixture stirred at RT for 30 min, followed by filtration, and concentration in vacuo. Purification via flash column chromatography (0-20% EtOAc/hexanes) afforded the title compound (1.82 g, 85%) as a white solid. LC-MS m/z 216 (M+H)+, 1.20 min (ret time).

According to the analysis of related databases, 179897-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXO GROUP LIMITED; BULLION, Ann, Marie; BUSCH-PETERSEN, Jakob; EVANS, Brian; NEIPP, Christopher, E.; MCCLELAND, Brent, W.; NEVINS, Neysa; WALL, Michael, D.; WO2011/25799; (2011); A1;,
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Application of 916792-13-7, 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. 916792-13-7, name is 4-Bromo-2-fluoro-5-methylbenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 4-bromo-2- fluoro-5-methylbenzonitrile (40 g, 190 mmol) in a mixture of sulfuric acid (98 %) and TFA (v/v=4:l, 480 mL) was stirred at 80 0C for 16 h. After the mixture was cooled to room temperature, the resulting mixture was poured into ice-cold water. The resulting precipitate was collected by filtration, washed with water and dried under reduced pressure to give the title compound (41 g, 95 % yield) as a white solid. MS (ESI) m/z 232.0 [M+l]+.

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-Bromo-2-fluoro-5-methylbenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; ELSNER, Jan; HARRIS, Roy, L.; LEE, Branden; MORTENSEN, Deborah; PACKARD, Garrick; PAPA, Patrick; PERRIN-NINKOVIC, Sophie; RIGGS, Jennifer; SANKAR, Sabita; SAPIENZA, John; SHEVLIN, Graziella; TEHRANI, Lida; XU, Weiming; ZHAO, Jingjing; PARNES, Jason; MADAKAMUTIL Loui; FULTZ Kimberly; NARLA, Rama K.; WO2010/62571; (2010); A1;,
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Synthetic Route of 50594-78-0, 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. 50594-78-0 name is 5-Fluoro-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 1 :To a solution of 2-methoxyethanol (9.6 ml_, 122 mmol) in THF at O0C was added NaH (60% in oil, 4.8 g, 122 mmol). The mixture was stirred at O0C for 15 min. To this solution was added 5-fluoro-2-nitrobenzonitrile (15.0 g, 103 mmol). The solution was then allowed to warm to RT and stirred at ambient temperature for 48 hours. The solution was partitioned between EtOAc and water. The water layer was extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified via flash chromatography (SiO2: gradient elution, 100:0 to 10:90 hexanes: EtOAc) to afford the ether (21.7 g, 95%) as a light yellow liquid.

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

Reference:
Patent; SCHERING CORPORATION; WO2009/5646; (2009); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts