Month: June 2021

Synthetic Route of 658-99-1, 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. 658-99-1, name is 2-(3,4-Difluorophenyl)acetonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation 10 4-Cyano-4-(3,4-difluorophenyl)-5-(1,3-dioxolan-2-yl)pentanoic acid A solution of 3,4-difluorobenzyl cyanide (20g, 0.13mol) in tetrahydrofuran (20ml) was added dropwise to a solution of lithium bis(trimethylsilyl)amide (1.0M, 144ml, 0,14mol) in tetrahydrofuran at 0C under nitrogen. The reaction mixture was allowed to warm to room temperature and stirred for 2 hours, after which time it was cooled to 0C and a solution of 2-bromomethyl-1,3-dioxolane (15ml, 0.14mol) in tetrahydrofuran (15ml) was added followed by tetra-n-butylammonium iodide (2g, 5.4mmol). The reaction mixture was warmed to room temperature and stirred for 18 hours. A further portion of solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (1M, 144ml, 0.14mol) was added dropwise to the reaction mixture at 0C and then the mixture was allowed to warm to room temperature over 5 hours. The reaction mixture was cooled to 0C and a solution of ethyl 3-bromopropionate (18ml, 0.14mol) in tetrahydrofuran (20ml) was added dropwise. The reaction mixture was allowed to warm to room temperature and stirred for 18 hours. A solution of sodium hydroxide (7.8g, 0.20mol) in water (50ml) was added to the crude reaction mixture at 0C and the mixture then allowed to warm to room temperature. The reaction mixture was stirred for 36 hours. The reaction mixture was partitioned between water and diethyl ether, the organic layer re-extracted with water and the combined aqueous layers were acidified to pH 1.0 with aqueous hydrochloric acid (2N). The aqueous layer was extracted with ethyl acetate (x2), dried over Na2SO4and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluding with a gradient system of dichloromethane gradually changing to dichloromethane: methanol: acetic acid (95: 5: 1, by volume) to afford the title compound as a brown oil (15.0g, 37%) which solidified on standing. 1H-NMR (CDCl3): delta = 7.30 (1H, m), 7.20 (2H, m), 4.80 (1H, m), 3.95 (2H, m), 3.80 (2H, m), 2.50 (2H, m), 2.30 (2H, m), 2.20 (2H, m). m/z: 312 (MH+).

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-(3,4-Difluorophenyl)acetonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER INC.; Pfizer Limited; EP992493; (2000); A1;,
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Reference of 185147-07-3, These common heterocyclic compound, 185147-07-3, name is 2-Fluoro-3-methylbenzonitrile, 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 81 : 3-Methyl-2-(2H-1 ,2,3-triazol-2-yl)benzonitrile.To a mixture of 2-fluoro-3-methylbenzonitrile (4.0 g, 29.6 mmol) and 2H-1 ,2,3- triazole (2.04 g, 29.6 mmol) in DMF (80 mL) was added potassium carbonate (8.26 g, 59.2 mmol). The resulting mixture was heated to 120 C for 2h. The mixture was cooled, diluted with water and extracted with EtOAc. The organic layers were combined, dried over Na2S04, filtered and concentrated. The residue was purified by FCC (Si02, ethyl acetate/hexanes, gradient 0-50%) to yield the title compound (1 .5 g, 26%). MS (ESI) mass calcd. for Ci0H8N4, 184.2; m/z found, 185.1 [M+H]+. 1H NMR (500 MHz, CDCI3): 7.95 (s, 2H), 7.66 (d, J = 7.7, 0.7 Hz, 1 H), 7.59 (d, J = 7.8, 0.6 Hz, 1 H), 7.50 (dd, J = 9.8, 5.7 Hz, 1 H), 2.20 (s, 3H).

The synthetic route of 185147-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; LETAVIC, Michael; RUDOLPH, Dale, A.; SAVALL, Brad, M.; SHIREMAN, Brock, T.; SWANSON, Devin; WO2012/145581; (2012); A1;,
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Application of 4088-84-0, A common heterocyclic compound, 4088-84-0, name is 2-Fluoro-5-trifluoromethylbenzonitrile, molecular formula is C8H3F4N, 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.

General procedure: 2-Fluoro-5-trifluoromethyl-benzonitrile (Matrix, 5.0 g, 26.5 mmol) and hydrazine (Aldrich, 1.28 g, 40 mmol) in IPA (10 mL) were heated to reflux for 2 hours. The solvent was removed to afford the title compound as white solid (5.3 g, 100%). MS: 202 (MH+).

The synthetic route of 4088-84-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Xuqing; Hufnagel, Heather; Hou, Cuifen; Opas, Evan; McKenney, Sandra; Crysler, Carl; O’Neill, John; Johnson, Dana; Sui, Zhihua; Bioorganic and Medicinal Chemistry Letters; vol. 21; 20; (2011); p. 6042 – 6048;,
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Adding a certain compound to certain chemical reactions, such as: 35202-54-1, name is 4,5-Dimethoxy-1-cyanobenzocyclobutane, 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 35202-54-1, name: 4,5-Dimethoxy-1-cyanobenzocyclobutane

A study using a number of bacterial inducers (propionitrile, benzonitrile, 4-bromobenzonitrile) showed that propionitrile provided the best induction of nitrilase activity with 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile. (0103) The bacterial strains were induced with propionitrile at 72 mM for 72 hours, and the cells were taken up in 50 mL (twice concentrated, conc. 10 mg of cells per ml) of 0.1M phosphate buffer KH2PO4/K2HPO4 pH=7.3 and 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile was added at a concentration of 10 mM in 2percent of DMSO v/vfinal. (0104) The fungal strains were induced with valeronitrile. (0105) All the reaction mixtures were stirred at 220 rpm at 30° C. in the case of the bacteria and at 27° C. in the case of the fungi and monitored for 96 hours by reverse-phase HPLC and by chiral-phase HPLC according to the methods described below: Reverse-Phase Analysis Chiral-Phase Analysis (0107) Chiralpak IC 250*4.6 column (0108) 30percent absolute ethanol+0.1percent TFA+70percent heptane+0.1percent TFA (0109) 1 ml/min 30° C. 288 nm The results obtained are collated in the Table below:

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; LES LABORATOIRES SERVIER; Pedragosa-Moreau, Sandrine; Lefoulon, Francois; (12 pag.)US9476071; (2016); B2;,
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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. 5866-98-8, name is 2,6-Dichloro-3-nitrobenzonitrile, A new synthetic method of this compound is introduced below., name: 2,6-Dichloro-3-nitrobenzonitrile

To a stirred solution of 2,6-dichloro-3-nitrobenzonitrile (750.0 g, 3.45 mol, 1.0 equiv.) in ethanol (7.5 L, 10.0 V) at 15-20 C. was slowly added hydrazine hydrate (519.0 g, 10.36 mol, 3.0 equiv.) while maintaining the reaction mass below 25 C (Observation: Addition is slightly exothermic and solid formation will begin upon addition). The reaction mixture temperature was slowly raised to room temperature and then the mixture was stirred for 3 h (Observation: the quantity of solids will increase during this time). After completion of the reaction (monitored by TLC), the mixture was diluted with water (7.5 L, 10.0 V) and further stirred for 1 h at room temperature. The solids were isolated via filtration and then were washed with water (2.25 L, 3.0 V). The wet solid was washed with a 1 : 1 ratio mixture of acetone (1.875 L, 2.5 V) and hexanes (1.875 L, 2.5 V). Bulk residual water was removed from the solids by maintaining vacuum filtration for 60-90 min. The wet solid was finally dried in a hot air oven for 7-8 h at 50 C (until moisture content reaches below 1.5%) to get the dried product, 4-chloro-7-nitro-li/-indazol-3 -amine (549.0 g, 75% yield) as a brick red-colored solid. NMK (400 MHz, CDCb): d 10.36 (bs, 1H), 8.20 (d, J= 8.4 Hz, 1H), 7.07 (d, J= 8.40 Hz, 1H), 4.73 (bs, 2H).

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; VIIV HEALTHCARE UK (NO.5) LIMITED; BOWSHER, Michael S.; GILLIS, Eric P.; IWUAGWU, Christiana; PARCELLA, Kyle E.; PEESE, Kevin M.; (125 pag.)WO2020/95177; (2020); A1;,
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Electric Literature of 691877-03-9, 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 691877-03-9 as follows.

A solution of 1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-5- (methoxycarbonyl)-3-methyl-1H-pyrazol-4-ylboronic acid (50 mg, 0.10 mmol), , 3-bromo-5- (trifluoromethyl)benzonitrile (31 mg, 0.12 mmol), Pd(PPh3)4 (12 mg, 0.10 mmol), Na2CO3 (54 mg, 0.51 mmol) in degassed 1,4-dioxane and H2O (4:1, 2.1 mL) was heated at 85 C for 18 hours. Water (5 mL) was added and the mixture was extracted with EtOAc (3x5mL). The combined organic layers were dried with sodium sulfate, filtered and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica gel using a solution of ethyl acetate in hexanes (2 to 10%) and afforded the title compound (23 mg, 0.037 mmol, 36%).

According to the analysis of related databases, 691877-03-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BANTAM PHARMACEUTICAL, LLC; SIDDIQUI, M., Arshad; CIBLAT, Stephane; DERY, Martin; CONSTANTINEAU-FORGET, Lea; GRAND-MAITRE, Chantal; GUO, Xiangyu; SRIVASTAVA, Sanjay; SHIPPS, Gerald, W.; COOPER, Alan, B.; BRUNEAU-LATOUR, Nicolas; LY, Vu, Linh; (314 pag.)WO2016/196644; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 87376-25-8, name is 2-Amino-4-nitrobenzonitrile, 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 87376-25-8, Product Details of 87376-25-8

General procedure: A mixture of 2-aminobenzonitrile 1a (0.3 mmol), trans-beta-nitrostyrene 2a (0.3 mmol), and CuBr (0.03mmol) in DMSO (2 mL) was stirred at 120 C for 8 hours till almost completed conversion of thesubstrates by TLC analysis. Then 30% NaCl solution (50 mL) was added to the mixture, which was thenextracted with EtOAc three times (3×50 mL). The extract was dried over anhydrous Na2SO4 andconcentrated in vacuo. The crude product was purified by column chromatography on silica gel (eluent:petroleumether/EtOAc) to afford the product 3a (70.8 mg, 89%) as a yellow solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Cai, Qun; Chen, Hui; Liao, Meng; Liu, Yi; Peng, Na; Sheng, Hui-Yang; Yang, Mian; Chemistry Letters; vol. 49; 5; (2020); p. 526 – 529;,
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2032-34-0, name is 3,3-Diethoxypropanenitrile, 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. Recommanded Product: 3,3-Diethoxypropanenitrile

General procedure: Method I. A mixture of Py (4.4 ml) and AcOH (3.0 ml) was stirred and treated by the addition of 5-aminoazole1a-h (0.01 mol) and (2E)-(3-morpholin-4-yl)-acrylonitrile (2) (1.38 g, 0.01 mol). The obtained mixture was refluxed at 150C for 5 h. After refluxing, the mixture was cooled. The precipitate that formed was filtered off, washed with a small amount of EtOH, and dried. Method II. A solution (or suspension) of the appropriate aminoazole 1a-h (0.01 mol) in solvent (15 ml) (EtOH in the case of compound 3a, dioxane in the case of compounds 3b-h) was stirred at 50C and treated by adding 3,3-diethoxypropionitrile (4) (1.5 ml, 0.01 mol), then 36% HCl solution (0.86 ml, 0.01 mol). The reaction mixture was refluxed for 2.5-3 h, the suspension (or solution) was cooled to room temperature, and the target product was isolated by the method indicated for each particular compound.

The synthetic route of 2032-34-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gazizov, Denis A.; Fedotov, Victor V.; Gorbunov, Evgeny B.; Ulomskiy, Evgeny N.; Yeltsov, Oleg S.; Rusinov, Gennady L.; Rusinov, Vladimir L.; Chemistry of Heterocyclic Compounds; vol. 55; 6; (2019); p. 573 – 577; Khim. Geterotsikl. Soedin.; vol. 55; 6; (2019); p. 573 – 577,5;,
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These common heterocyclic compound, 123-06-8, name is Ethoxymethylenemalononitrile, 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. category: nitriles-buliding-blocks

To a stirred (m)ethanolic solution (only 5b in methanol) of hydrazine hydrate (17.2 mmol) was added enol ether 3a-d (17.2 mmol) dropwise at rt. The reaction mixture was heated under reflux for 1-1.5 h. After cooling the crude product was filtered and recrystallized from the appropriate solvent or purified by column chromatography.

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

Reference:
Article; Tarabova, Denisa; Soralova, Stanislava; Breza, Martin; Fronc, Marek; Holzer, Wolfgang; Milata, Viktor; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 752 – 760;,
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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. 4640-67-9, name is 3-(4-Fluorophenyl)-3-oxopropanenitrile, A new synthetic method of this compound is introduced below., Quality Control of 3-(4-Fluorophenyl)-3-oxopropanenitrile

General procedure: 4.2.1. Method (A) A mixture of 3 (1.18 g, 5 mmol), beta-ketonitrile (5 mmol) and 4-anisaldehyde (0.68 g, 5 mmol) in acetic acid (20 ml) and in the presence of TEA (1 ml) was heated under reflux for 4 h. The reaction mixture was poured into crushed ice (20 ml) and the solid obtained was collected by filtration, washed with water (3 × 10 ml) and recrystallized from ethanol to give pure 4. 4.2.2. Method (B) The procedure was similar to that described in Method A except that the mixture was capped in closed vessels and irradiated in a microwave oven at 150 C for 15 min using Synthos 3000 (500 W). The reaction was worked and the solid obtained was recrystallized from ethanol to give 4.

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:
Article; El-Borai; Rizk; Abd-Aal; El-Deeb; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 92 – 96;,
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