Month: July 2021

Reference of 1558-81-2, These common heterocyclic compound, 1558-81-2, name is Ethyl 1-Cyano-1-cyclopropanecarboxylate, 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.

Example 97A (Enantiomer 1)Step V ” l-(hydroxymethyl)cycJopropanecarbonitriotale; HO “^ANi NAt r.t to a solution of ethyl 1-cyanocyclopropanecarboxylate (1.0 g, 7.2 mmol; Aldrich, Cat. No. 543055) in tetrahydrofuran (15 mL) was added lithium tetrahydroborate (0.31 g, 14 mmol) portionwise with stirring. The resuting mixture was heated at reflux for 3 h. After cooling, it was quenched with water. The product was extracted with ethyl acetate. The extract was washed with water and brine, dried over Na2SO4. After filtration the filtrate was concentrated to yield 0.41 g of the product which was used directly in next step reaction without further purification.

The synthetic route of 1558-81-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INCYTE CORPORATION; ZHANG, Colin; QIAN, Ding-quan; ZHUO, Jincong; YAO, Wenqing; WO2010/75270; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 97165-77-0, name is 3,5-Dibromobenzonitrile, 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 97165-77-0, Quality Control of 3,5-Dibromobenzonitrile

3,5-dibromobenzene cyanide (20.0 mmol) under nitrogen protection,1-THP-4-pyrazoleboronic acid pinacol ester (48.0 mmol) and 1,4-dioxane (120 mL) and water (30 mL) were added to a 250 mL round bottom flask.Add magnetron stirring, then add K2CO3 (60.0mmol)And Pd(PPh3)4 (1.0 mmol), the reaction was stirred at 100 C for 24 hours. After the reaction is completed, the solvent of the reaction system is spin-dried.The residue was dissolved in ethyl acetate (200 mL).Wash with water (150 mL × 2) and saturated brine (200 mL),After drying over anhydrous Na 2 SO 4 , filtered and concentrated.The crude product was purified by column chromatography (SiO2, petroleum ether / ethyl acetate = 20:1 to 1:1).After concentration, 3,5-bis(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)phenyl cyanide was obtained as a pale yellow solid (yield: 84%).

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; Beijing University of Technology; Li Jianrong; Kong Xiangjing; Zhang Yongzheng; He Tao; (10 pag.)CN109851559; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 668-45-1, name is 2-Chloro-6-fluorobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Chloro-6-fluorobenzonitrile

a 2-Chloro-6-methoxybenzonitrile 2-Chloro-6-fluorobenzonitrile (Aldrich, 5.0 g, 32.1 mmol) was dissolved in MeOH (100 mL), NaOMe (7.4 mL of 25% wt. solution, 32.1 mmol) and refluxed 18 h. The mixture was concentrated poured into EtOAc/H2O and extracted with EtOAc to give the title compound (5.3 g, 59%).

According to the analysis of related databases, 668-45-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SmithKline Beecham Corporation; US6294531; (2001); B1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 6621-59-6, name is 6-Bromohexanenitrile, A new synthetic method of this compound is introduced below., Product Details of 6621-59-6

General procedure: To a magnetically stirred solution of 131 mg isoindigo 1(0.5 mmol) in 3 cm3 DMF, 59.4 mg sodium methoxidesolution (1.1 mmol) was added in 2 cm3 DMF at roomtemperature. The reaction mixture stirred for 30 min, followedby the addition of the alkyl bromide (3 mmol) andthe reaction stirred for 6 h at 45 C. The mixture waspoured into 10 cm3 H2O, extracted with 20 cm3 CH2Cl2,dried (MgSO4), and the solvent was removed underreduced pressure. The residue was subjected to silica gelcolumn chromatography using hexane-ethyl acetate aseluent.

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; Khalili, Gholamhossein; Willis, Anthony C.; Keller, Paul A.; Monatshefte fur Chemie; vol. 149; 11; (2018); p. 2103 – 2111;,
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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. 19472-74-3, name is 2-Bromophenylacetonitrile, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6BrN

General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60-90 C)-EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60-90C)-EtOAc, 10:1 to 30:1] to give 3af; Yield: 59.2 mg (93%); fluorescent yellow solid; mp 205.6-207.1 C.

The synthetic route of 19472-74-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jiang, Zeng-Qiang; Miao, Da-Zhuang; Tong, Yao; Pan, Qiang; Li, Xiao-Tong; Hu, Ren-He; Han, Shi-Qing; Synthesis; vol. 47; 13; (2015); p. 1913 – 1921;,
Nitrile – Wikipedia,
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Related Products of 3939-09-1, These common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, 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: Aromatic or aliphatic nitriles (2 mmol) were dissolved in 5 ml of [bmim]HSO4 and the reaction mixture was heated at 60-65 C for 1-3 h. The progress of reaction was monitored by TLC. After completion of reaction, as checked by TLC, the reaction mixture was poured into water containing crushed ice. The product was precipitated out, filtered and dried. The yield of the final product was high (>90%) in all cases. All final products obtained were found sufficiently pure so it didn?t need further purification.The filtrate was concentrated under vacuum, washed with diethylether twice and concentrated under high vacuum. After proper drying under reduced pressure, approximately 95% ionic liquid was recovered from the reaction and compared with the original ionic liquid to check its authenticity. The efficiency of recovered ionic liquid in conversion of nitriles to acids was found unchanged in comparison to the original one and we reused it up to 5-6 cycles without any significant loss of its activity.

Statistics shows that 2,4-Difluorobenzonitrile is playing an increasingly important role. we look forward to future research findings about 3939-09-1.

Reference:
Article; Kumar, Satyanand; Dixit, Sandeep Kumar; Awasthi, Satish Kumar; Tetrahedron Letters; vol. 55; 28; (2014); p. 3802 – 3804;,
Nitrile – Wikipedia,
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Synthetic Route of 2469-99-0,Some common heterocyclic compound, 2469-99-0, name is 3-Oxobutanenitrile, molecular formula is C4H5NO, 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 stirring suspension of 4-hydrazinylisoqui- noline (0.32 g, 2.0 mmol) and 3-oxo-butyronitrile (0.16 g, 0.19 mmol) in ethanol (10 mE) was heated at 80 C. for 3 h. After cooling to room temperature, 20% aqueous sodium hydroxide (1 mE) was added to the reaction mixture and was further heated at 80 C. for 1 h. The reaction mixture was cooled to room temperature and concentrated in vacuo. The crude residue was dissolved in 1: 1 dichloromethane/methanol (40 mE) and the phases were separated. The organic layer was dried (Na2SO4), and filtered through a pad of Celite. The filtrate was concentrated in vacuo and the crude residue was purified by flash chromatography (Si02, 50-100% ethyl acetate in hexanes) to give the desired product (0.36 g, 1.6 mmol, 81%)

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

Reference:
Patent; ChemoCentryx, Inc.; Cappel, Markus; (83 pag.)US2018/9797; (2018); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 622-75-3, name is 2,2′-(1,4-Phenylene)diacetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2,2′-(1,4-Phenylene)diacetonitrile

Add 3,4-bis (2-oxiranylmethoxy) benzaldehyde (0.01mol, 0.25g), terephthalonitrile (0.0045mol, 0.7000g), and 150mL of ethanol to a 250mL single-necked bottle in this order. After stirring for about 10 minutes, solid sodium hydroxide (0.02 mol, 0.80 g) was added, and the reaction was stopped after about 5-6 hours.After the reaction system was cooled to room temperature, suction filtration was performed to collect the solid product, washed with water, and dried to obtain a crude product. The crude product was recrystallized from a mixed solvent of DMF and ethanol (V: V = 3: 1) to obtain 2.65 g of a pure product. The yield was 94%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 622-75-3.

Reference:
Patent; Xiangtan University; Zhang Hailiang; Tan Huiping; Yuan Yongjie; Yang Bohao; (15 pag.)CN110407772; (2019); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 3939-09-1,Some common heterocyclic compound, 3939-09-1, name is 2,4-Difluorobenzonitrile, molecular formula is C7H3F2N, 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.

Step 1: To a 0 C. solution of LiHMDS (360 mL, 359.5 mmol) in 148 THF (200 mL) was added drop wise, 439 2,4-difluorobenzonitrile (20 g, 143.8 mmol) in THF (100 mL). The reaction was warmed to rt and stirred for 4 hrs and c.HCl (100 mL) was added drop wise to keep the temperature below 30 C. 81 EtOAc was added and the aqueous layer was collected. The pH was adjusted to 10 by the careful addition of 6N 344 NaOH and the organic layer collected, dried and evaporated to dryness to give 440 2,4-difluoro benzimidamide (10 g, 44%) which was used without further purification in Step 2.

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

Reference:
Patent; CYSTIC FIBROSIS FOUNDATION THERAPEUTICS, INC.; Strohbach, Joseph Walter; Limburg, David Christopher; Mathias, John Paul; Thorarensen, Atli; Denny, Rajiah Aldrin; Zapf, Christoph Wolfgang; Elbaum, Daniel; Gavrin, Lori Krim; Efremov, Ivan Viktorovich; (159 pag.)US2018/141954; (2018); A1;,
Nitrile – Wikipedia,
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Application of 10412-93-8, These common heterocyclic compound, 10412-93-8, name is N-Benzyl-2-cyanoacetamide, 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.

5.6. Synthesis Of (E)-2-(benzylaminocarbonyl)-3-(3-iodo-4,5-dihydroxyphenyl)acrylonitrile A preferred method of synthesis of (E)-2-(benzylaminocarbonyl)-3-(3-iodo-4,5-dihydroxyphenyl)acrylonitrile (Compound 6) is as follows: A mixture of 0.4 g of 2-cyano-3-(4-hydroxy-3-iodo-5-methoxy)phenylacrylonitrile (which was prepared by condensation of 4-hydroxy-3-iodo-5-methoxybenzaldehyde with N-benzylcyanoacetamide) and 0.5 ml of BBr3 in 20 ml dichloromethane was stirred for 2 hours at room temperature. Workup (H2 O, ethyl acetate) gave 0.16 g of a yellow solid (41 yield) having a melting point of 220 C. The product gave the following analytical data: NMR (acetone-d6) delta 8.05(1H,S,vinyl), 7.85(1H,d,J=2.1 Hz), 7.70(1H,d,J=2.1 Hz), 7.30(5H,in), 4.6(2H,S).

Statistics shows that N-Benzyl-2-cyanoacetamide is playing an increasingly important role. we look forward to future research findings about 10412-93-8.

Reference:
Patent; Sugen, Inc.; Yissum Research Development Co. of the Hebrew University of Jerusalem; US5792771; (1998); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts