Month: May 2021

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. 10365-94-3, name is 1,3,5-Benzenetricarbonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3,5-Benzenetricarbonitrile

(3) 100 g of 1,3,5-benzotrinitrile and 3 g of Raney-Ni, 400 mL of ethanol are added to a 1 L hydrogenation reactor, and H2 is continuously charged, so that the pressure of the system is always maintained at 8 MPa during the reaction. After the reaction was performed at a reaction temperature of 110 C. for 1.5 h, the temperature was lowered. When the temperature in the reaction vessel was lowered to room temperature, the gas was purged, and 1,3,5-benzenetrimethylamine (having a purity of 99% or more) was obtained by filtration and recrystallization. The yield was 88% by weight.

According to the analysis of related databases, 10365-94-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Sinopec Yangzi Petrochemical Co., Ltd.; Sinopec Corporation; Sun Hailong; Li Na; Gao Yilong; Wei Yanyu; Chen Xinhua; Miao Jun; Kan Lin; Bai Jiye; Chen Shaohui; Yang Aiwu; Xu Yuexing; (30 pag.)CN105001032; (2018); B;,
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Application of 262298-02-2,Some common heterocyclic compound, 262298-02-2, name is 4-Methoxy-2-methylphenylacetonitrile, molecular formula is C10H11NO, 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 2 1-cyano-1-(2-methyl-4-methoxyphenyl)propan-2-one Under argon atmosphere, to a solution of the compound prepared in reference example 1 (11.7 g) in ethyl acetate (60 ml), metallic sodium (2.3 g) was added in numbers. The mixture was stirred for 2 hours at 50 §C. Ethyl acetate (40 ml) was added to the reaction mixture, and the mixture was refluxed for 2.5 hours and then it was stirred overnight at room temperature. A precipitation matter was collected by filtration, and it was washed with diethyl ether. The obtained crystal was dissolved into water (300 ml). The solution was adjusted pH 4 by adding 2N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated to give the title compound (12.06 g) having the following physical data. TLC: Rf 0.45 (n-hexane: ethyl acetate = 1: 1).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Methoxy-2-methylphenylacetonitrile, its application will become more common.

Reference:
Patent; ONO PHARMACEUTICAL CO., LTD.; EP1354884; (2003); A1;,
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Synthetic Route of 35764-15-9, These common heterocyclic compound, 35764-15-9, name is 2-Bromo-4-(trifluoromethyl)benzonitrile, 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.

Into a 5 mL microwave vial were charged methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5- tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoate (300 mg, 0.85 mmol), 2-bromo-4- (trifluoromethyl)benzonitrile (425 mg, 1.70 mmol), cesium carbonate (1.38 g, 4.25 mmol), tetra-n- butylammonium iodide (314 mg, 0.85 mmol), POPd (43 mg, 0.085 mmol), water (0.6 mL) and NN- dimethylformamide (3 mL). The reaction mixture was subjected to microwave irradiation at 150 0C for 10 mins. After cooling, the reaction mixture was extracted with ethylacetate. The organic layer was washed with brine, dried, and concentrated under reduced pressure to afford the residue which was purified by silica gel column to yield the title compound.

The synthetic route of 35764-15-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; WEI, Zhi-Liang; GOWLUGARI, Sumithra; KAUB, Carl; WANG, Zhan; CAO, Yeyu; KINCAID, John; WO2010/33168; (2010); A2;,
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Application of 5312-97-0, A common heterocyclic compound, 5312-97-0, name is 2,5-Dimethoxybenzonitrile, molecular formula is C9H9NO2, 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.

Intermediate 42a) To solution of 2,5-dimethoxybenzonitrile (1.5 g) in dry Et20 (7 mL) was added propyl magnesium chloride (2 M in Et20, 9.2 mL) and the resulting mixture was heated to 40 C for 2 h. The mixture was chilled and 4 M HCI (9 mL) was carefully added and it was stirred at ambient temperature for 16 h. The mixture was extracted with EtOAc, the combined organic layers were washed with water, were dried and the volatiles were removed under reduced pressure. The residue was purified by column chromatography (Interchim cartridge 15SiHP / 120 g, Cy / EtOAc) to yield the desired compound (57% yield). LC-MS {Method 1): m/z [M+Hf = 209.3 (MW calc. = 208.25); R, = 3.5 min.

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; GRUeNENTHAL GMBH; NORDHOFF, Sonja; WACHTEN, Sebastian; KLESS, Achim; VOSS, Felix; RITTER, Stefanie; WO2014/108336; (2014); 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 64113-85-5 as follows. category: nitriles-buliding-blocks

General procedure: The heterocyclic derivative (0.99 mmol) and 5 mL THF is cooled to -78 oC, n-BuLi solution ( 0.5, mL, 1.2 eq) is added, the mixture is stirred 1 hr, after which 2-cyano-4-methyhlbiphenyl (192 mg, 0.99 mmol, dissolved in 5 mL THF) is added dropwise, The solution is then stirred 1 hr at -78 oC, then allowed to warm to room temperature and stirred for 6 hr. After this, 10 mL of 6M HCl is added and the mixture is stirred overnight. The solution is then basified with 10M NaOH and the products are partitioned between ether and water. The aqueous layer is further extracted (2x with ether) and the combined extracts are washed with brine, dried over anhydrous sodium sulfate, and filtered. The solvent is then removed under reduced pressure and the crude mixture is purified by column chromatography (1:1, hexanes: ethyl acetate).

According to the analysis of related databases, 64113-85-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Stentzel, Michael R.; Klumpp, Douglas A.; Tetrahedron Letters; vol. 60; 25; (2019); p. 1675 – 1677;,
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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. 6283-71-2, name is Dimethyl 2-cyanosuccinate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Dimethyl 2-cyanosuccinate

Preparation 100; 1- [2, 6-dichloro-4-pentafluorothiophenyl]-5-hydroxy-1 H-pyrazole-3-carbonitrile; Sodium nitrite (1.32 g, 19.1 mmol) was added carefully to sulphuric acid (concentrated, 6.8 ml), whilst cooling the solution to 0°C. The solution was heated to 60°C for 30 min, allowed to cool and then diluted with acetic acid (12 ml). To the solution was added 2, 6-dichloro-4-pentafluorothiophenylamine (WO 9421606 A1, 5.0 mg, 17.4 mmol) in acetic acid (11 ml) and the reaction mixture was heated at 55°C for 1 h. To a solution of dimethyl 2-cyanosuccinate (Hall, H. K. , Jr.; Ykman, P. , J. Am. Chem. Soc. (1975), 97 (4), 800-807,3. 09 g, 18.1 mmol) in acetic acid (24 mi) and water (36 ml) was added dropwise the solution of the diazonium salt, followed by sodium acetate (24.2 g) in water (42 ml). The reaction mixture was then stirred at room temperature for 30 min. The reaction mixture was poured into ice/water (200 ml) and the mixture was extracted with dichloromethane (4 x 60 ml). The combined extracts were then washed with ammonium hydroxide (48 ml), dried and concentrated in vacuo. To a solution of sodium methoxide (25 wt. percent, 11.5 ml, 50.1 mmol) in methanol (450 ml) was added dropwise a solution of the residue in methanol (100 ml). The reaction mixture was then stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and to the residue was added water. This solution was adjusted to pH 1 by addition of hydrochloric acid (4N) and the mixture was extracted with dichloromethane (3 x 100 ml). The combined extracts were dried (MgS04) and concentrated in vacuo. The residue was purified by column chromatography, eluting with hexane/ethyl acetate [3: 1]. The appropriate fractions were combined and concentrated to give the titled compound (4. 5g). Experimental MH+ 379.8 ; expected 380.0

The synthetic route of 6283-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/90313; (2005); A1;,
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Application of 916792-09-1,Some common heterocyclic compound, 916792-09-1, name is 2-Bromo-4-fluoro-6-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.

2-Bromo-4-fluoro-6-methyl-benzonitrile (IX) (0.428 g, 2 mmol) was heated in 70% aqueous sulfuric acid (2 mL)overnight at 150 00 The reaction mixture was poured into ice and extracted with ethyl acetate (4 x 2 mL). The organic phase was washed with water (4 x 2 mL), brine (2 x 2 mL), dried over Na2SO4, filtered and concentrated to give 300 mg of crude 2-bromo-4-fluoro-6-methyl-benzamide (VIII). Pure sample was obtained by recrystallization from benzene. 1H NMR (400.5 MHz, DMSO-d6) ppm 3.31 (s, 3H), 7.17 (dd, JH-F = 9.8 Hz, JH-H 2.2 Hz, 1H), 7.41 (dd, JH-F 8.6Hz, JH-H = 2.2 Hz, 1H), 7.89 (br. s, 1H), 7.65 (br. s, 1H).

The synthetic route of 916792-09-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; PAPEO, Gianluca Mariano Enrico; KRASAVIN, Mikhail Yurievitch; ORSINI, Paolo; SCOLARO, Alessandra; WO2014/64149; (2014); A1;,
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Adding a certain compound to certain chemical reactions, such as: 406719-76-4, name is Methyl 4-cyano-2-methoxybenzoate, 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 406719-76-4, Application In Synthesis of Methyl 4-cyano-2-methoxybenzoate

A mixture of 4-cyano-2-methoxy-benzoic acid methyl ester (1.01 g, 5.28 mmol) in methanol (50 mL) was added to Raney-nickel 2800 slurry in water (a few grams washed with methanol to remove the water, Aldrich) and it was put under a 50 psi hydrogen atmosphere for 16 hrs. The mixture was filtered through Celite under an argon atmosphere and concentrated and then purified by flash chromatography to give 4-aminomethyl-2-methoxy-benzoic acid methyl ester (385.7 mg, 34.7%).

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, Methyl 4-cyano-2-methoxybenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bartkovitz, David Joseph; Chu, Xin-Jie; Liu, Jin-Jun; Morgan Ross, Tina; Zhang, Zhuming; US2011/86854; (2011); A1;,
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10444-38-9, name is Ethyl 4-cyanobutanoate, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C7H11NO2

General procedure: A 1 M solution of LiHMDS in THF (5.1 eq) was added slowly to a solution of NH2OBn.HCl (1.1 eq.) in THF (4 mL/mmol) at -78C. The mixture was stirred 30 min before the addition of the nitrile (1 eq). After total consumption of the starting materials (TLC), the reaction was quenched with a saturated aqueous solution of NH4Cl, warmed up to room temperature, and extracted three times with AcOEt. The collected organic layers were dried over Na2SO4, filtered and evaporated to dryness under reduced pressure.

The synthetic route of 10444-38-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nguyen-Trung, Anh Thu; Tritsch, Denis; Grosdemange-Billiard, Catherine; Rohmer, Michel; Bioorganic and Medicinal Chemistry Letters; vol. 23; 6; (2013); p. 1643 – 1647;,
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These common heterocyclic compound, 28442-78-6, name is 2-Chloroisophthalonitrile, 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. Quality Control of 2-Chloroisophthalonitrile

EXAMPLE 55A 3-Amino-2-carbomethoxy-7-cyano-benzthiophene 2-chloro-1,3-dicyanobenzene (972 mg, 6.0 mmol) was treated with 1 eq of methyl thioglycolate and 1 eq sodium carbonate in methanol as described in Example 41A to give the title compound in 65% yield. 1H NMR (300 MHz, D6-DMSO d 3.83 (s, 3H), 7.38 (bs, 2H), 7.62 (t, J=8 Hz, 1H), 8.10 (d, J=8 Hz, 1H), 8.50 (d, J=8 Hz, 1H). MS (DCI/NH3) m/e 250 (M+NH4)+.

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

Reference:
Patent; Abbott Laboratories; US5597823; (1997); A;,
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