Month: June 2021

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. 939-79-7, name is 4-Methyl-3-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: nitriles-buliding-blocks

To a mixture of 4-bromobenzaldehyde (2; 100g, 543 mmol) and piperidine (26 mL, 260 mmol) was added 4-cyano-2-nitrotoluene (1; 92 g, 567mmol). The resulting slurry was heated at 125 C for 4 h until it became a solid. After cooling to room temperature, CH2Cl2 (200 mL) was added to the solid mass and the mixture was stirred for 30 min. To the resulting mixture was added hexane (200mL), and the suspension was stirred at room temperature overnight. The solid was filtered, washed with hexane (1 L), and dried under vacuum to provide 178 g (99 %) of product as yellow solid, which was used in the next step without further purification.

The synthetic route of 939-79-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nguyen, Son T.; Williams, John D.; Butler, Michelle M.; Ding, Xiaoyuan; Mills, Debra M.; Tashjian, Tommy F.; Panchal, Rekha G.; Weir, Susan K.; Moon, Chaeho; Kim, Hwa-Ok; Marsden, Jeremiah A.; Peet, Norton P.; Bowlin, Terry L.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 15; (2014); p. 3366 – 3372;,
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Synthetic Route of 19924-43-7,Some common heterocyclic compound, 19924-43-7, name is 2-(3-Methoxyphenyl)acetonitrile, molecular formula is C9H9NO, 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: Amidoxime Formation To a solution of nitrile (1 eq.) in EtOH (12 mL mmol-1) was added hydroxylamine (50% v/v in H20, 4 mL mmol-1) and the reaction mixture heated under reflux for 5 hours. After removal of all volatiles under reduced pressure the crude produce was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(3-Methoxyphenyl)acetonitrile, its application will become more common.

Reference:
Patent; IMPERIAL INNOVATIONS LIMITED; LEATHERBARROW, Robin; TATE, Edward; YU, Zhiyong; RACKHAM, Mark; WO2013/83991; (2013); A1;,
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Related Products of 52798-01-3, These common heterocyclic compound, 52798-01-3, name is Methyl (4-cyanophenyl)acetate, 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.

(4-Cyano-phenyl)-acetic acid methylester (1.054 g, 6.02 mmol), hydroxylamine hydrochloride (0.690 g, 9.93 mmol) and sodium bicarbonate (0.834 g, 9.93 mmol) were dissolved in MeOH (12.03 mL) at RT. The mixture was stirred at 60 C for 5 h, diluted with EtOAc (200 mL) and 40 ml water added. The aqueous layer was extracted with EtOAc (100 mL). The combined organic phases were washed with brine (40 mL) and dried over sodium sulfate. Solvent was removed to yield 1.2 g (5.76 mmol) of yellow oil, which was dried on high vacuum over night. The crude mixture was used without further purification.

Statistics shows that Methyl (4-cyanophenyl)acetate is playing an increasingly important role. we look forward to future research findings about 52798-01-3.

Reference:
Patent; NOVARTIS AG; HEBACH, Christina; JOLY, Emilie; KALLEN, Joerg; TERNOIS, James Gilbert; TINTELNOT-BLOMLEY, Marina; WO2013/8162; (2013); A1;,
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Related Products of 5866-98-8, 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. 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 11A 6-Chloro-2-ethylamino-3-nitro-benzonitrile A solution of ethylamine in THF (2 M, 13.8 mL, 27.6 mmol) was added slowly to a solution of 2,6-dichloro-3-nitrobenzonitrile (3.0 g, 13.8 mmol) in THF (30 mL) at -5 C. After 1.5 h, the solution was diluted with EtOAc (150 mL) and washed with 0.5 N HCl and brine. Organics were dried (MgSO4) and concentrated in vacuo. Purification by silica gel chromatography (8:1:1 hexanes/CHCl3/EtOAc) gave 2.57 g (82%) of the title compound as an orange solid. 1H NMR (400 MHz, CDCl3): delta 8.51 (br s, 1H), 8.30 (d, 1H, J=8.8 Hz), 6.78 (d, 1H, J=8.4 Hz), 3.89-3.97 (m, 2H), 1.41 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc’d for C9H8N3O2Cl, 226, 228; found 226, 228.

The synthetic route of 2,6-Dichloro-3-nitrobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Feng, Jun; Gwaltney, Stephen L.; Wallace, Michael B.; Zhang, Zhiyuan; US2005/272765; (2005); A1;,
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Reference of 40497-11-8, 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 40497-11-8 as follows.

0.01 mol of ethyl 2,3-dicyanopropionate was added to a three-necked flask. The prepared diazonium salt solution was dropped into the flask. The reaction was complete for 2 h. Adding aqueous ammonia, adjust the pH to 9-10. Reaction at room temperature for 2h. After completion of the reaction, the reaction mixture was extracted with 40 mL of dichloromethane. The organic layer was washed with water (2 x 30 mL), washed with saturated sodium chloride solution (1 x 40 mL), and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 2.10 g of product, yield 75.2%.

According to the analysis of related databases, 40497-11-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Nanjing University of Technology; Wan, Rong; Wu, Shaohua; Guo, Chunwei; Guan, Xilin; Chen, Fuli; Han, Zhenyu; Fu, Xiaohuan; (14 pag.)CN105601632; (2016); A;,
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Electric Literature of 77326-36-4, 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. 77326-36-4, name is 2-Amino-6-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 2: Methyl- (2-cyano-3-methoxy-phenyl) sulfonamide; 2.1 : 2-Amino-6-methoxy-benzonitrile A solution of 70 g (0.5 mol) of 2-amino-6-fluoro-benzonitrile (prepared, e. g. according to US 4,504, 660) in 250 ml of N, N-dimethylformamide was initially charged and a solu- tion of 30.6 g (0.55 mol) sodium methoxide in 70 ml of methanol was added dropwise at room temperature while stirring. The mixture was then refluxed for 5 hours under stirring. The completion of the reaction was monitored by TLC. Additional 25 g of so- dium methoxide in 35 ml methanol were added and the reaction mixture was refluxed for additional 4 hours while stirring. The reaction mixture was concentrated under re- duced pressure, the resulting residue was triturated with water, sucked off and the ob- tained solids were dissolved in ethyl acetate. The resulting solution was concentrated in vacuo. The obtained residue was triturated with petroleum ether and sucked off to afford 48 g (63% of theory) of a brownish solid having a melting point of 143-146C.

The synthetic route of 2-Amino-6-fluorobenzonitrile has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF AKTIENGESELLSCHAFT; WO2005/35486; (2005); A1;,
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Related Products of 145689-34-5, 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. 145689-34-5 name is 2-(2,3-Difluorophenyl)acetonitrile, 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 65; 2-[1-(2,3-Difluoro-phenyl)-ethyl]-4,5-dihydro-1H-imidazole; a) rac-2-(2,3-Difluoro-phenyl)-propionitrile; A solution of 1.586 g (16 mmol) diisopropylamine in 25 ml tetrahydrofuran was cooled with sodium chloride/ice to -10 C. A solution of 9 ml (14 mmol) 1.6 M butyl lithium in hexanes was added drop-wise. After stirring for 10 min the resulting LDA solution was cooled to -78 C. and a solution of 2.00 g (13 mmol) 2,3-difluorophenyl-acetonitrile in 5 ml tetrahydrofuran slowly added. The reaction mixture was stirred at -78 C. for 40 min, then 2.22 g (16 mmol) methyl iodide were added and the cooling bath was removed after 5 min. The mixture was stirred for 2.5 h at room temperature, and then aqueous ammonium chloride solution was added. The mixture was extracted twice with ethyl acetate. The combined organic layers were dried over MgSO4, filtered and evaporated. The residue was purified using column chromatography (SiO2, heptanes/ethyl acetate 9:1) to yield 1.12 g of rac-2-(2,3-difluoro-phenyl)-propionitrile as a light yellow liquid; MS (EI): 167.1 (M+·), 152.1 (((M-CH3)+·), 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2,3-Difluorophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Galley, Guido; Zbinden, Katrin Groebke; Hoener, Marius; Kolczewski, Sabine; Norcross, Roger; Stalder, Henri; US2007/197621; (2007); 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 17354-04-0 as follows. Formula: C10H10N2O4

General procedure: Piperidine (0.03 ml, 5 mol %) was added to a warm solution of the appropriate salicylaldehyde 5 (5 mmol) and 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile (1.12 g, 5 mmol) in EtOH (10 ml). The resulting solution was refluxed with stirring for 5 h. The mixture was treated with a solution of concentrated H2SO4 (0.55 ml) in EtOH (2 ml) and refluxed with stirring for 2 h. The obtained precipitate was filtered, washed with EtOH (10 ml), hot H2O (40 ml) and finally with EtOH (10 ml), and dried at 100 C.

According to the analysis of related databases, 17354-04-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Irgashev, Roman A.; Karmatsky, Arseny A.; Slepukhin, Pavel A.; Rusinov, Gennady L.; Charushin, Valery N.; Tetrahedron Letters; vol. 54; 42; (2013); p. 5734 – 5738;,
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Some common heterocyclic compound, 916792-13-7, name is 4-Bromo-2-fluoro-5-methylbenzonitrile, molecular formula is C8H5BrFN, 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. Recommanded Product: 4-Bromo-2-fluoro-5-methylbenzonitrile

To a solution of 4-bromo-2-fluoro-5-methylbenzonitrile (10.0 g, 46.7 mmol) in N,N-dimethylacetamide (30 mL) was added Pd(dppf)Cl2 (5.1 g, 7.0 mmol) and MeOH (10 mL), followed by TEA (14.3g, 140.1 mmol). The mixture was heated at 90 C overnight under carbon monoxide (5 MPa). The mixture was cooled to RT and the mixture was diluted with water, extracted with EA. The combined organic layers were concentrated to give the crude product, which was purified by silica gel chromatography eluting with EA/petroleum ether from 5% to 10% to give methyl 4-cyano-5-fluoro-2-methylbenzoate (7.33 g, 81%) as a white solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 916792-13-7, its application will become more common.

Reference:
Patent; BIOTHERYX, INC.; MERCURIO, Frank; CHAN, Kyle, W.H.; SULLIVAN, Robert; ERDMAN, Paul, E.; FUNG, Leah; (105 pag.)WO2018/169777; (2018); 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. 3215-64-3, name is 2-(2,6-Dichlorophenyl)acetonitrile, A new synthetic method of this compound is introduced below., Product Details of 3215-64-3

A mixture of 6-chloro-4-(ethyl amino) nicotinaldehyde (Scheme 1 compound 6) (1.20 g, 6.52 mmol), 2-(2,6-dichlorophenyl)acetonitrile (1.57 g, 8.47 mmol) and K2C03 (2.70 g, 19.56 mmol) in dry DMF (12 mL) was heated to 100 C under nitrogen atmosphere for 16 h. After TLC showed the starting material was completely consumed, the reaction mixture was cooled to RT, diluted with EtOAc (100 mL), washed with water (2 x 30 mL) and brine (20 mL) then dried over Na2S04 and concentrated to give a residue which was purified by flash chromatography on silica gel (eluting with petroleum ether/EtOAc 100/0 gradually increasing to 70/30) to give 7-chloro-3-(2,6-dichlorophenyl)-l-ethyl-l,6-naphthyridin-2(lH)-imine (1.5 g, 45%) as a black gummy solid. 1H NMR (400 MHz, DMSO-d6): delta 8.45 (d, J= 4.7 Hz, 1H), 7.66 (d, J= 8.1 Hz, 2H), 7.56 (t, J= 7.2 Hz, 1H), 7.50 (s, 1H), 7.45 (s, 1H), 6.85 (d, J= 10.0 Hz, 1H), 4.30 (s, 2H), 1.22-1.16 (m, 3H). MS [ESI, MH+] = 352.05.

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; MANNKIND CORPORATION; TOLERO PHARMACEUTICALS, INC.; ZENG, Qingping; FARIS, Mary; MOLLARD, Alexis; WARNER, Steven L.; FLYNN, Gary A.; WO2014/52365; (2014); A1;,
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