Category: nitriles-buliding-blocks

50397-74-5, name is 4-Amino-3-bromobenzonitrile, 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. name: 4-Amino-3-bromobenzonitrile

50.0 g (253.76 mmol) of 4-amino-3-bromobenzonitrile, 4-bromobenzoyl chloride 55.7 g (253.76 mmol) of (4-bromobenzoyl chloride) and 500 mL of pyridine were added thereto, followed by stirring at reflux for at least 12 hours. After the reaction was completed, the solvent was distilled off under reduced pressure. Solid to pale yellow by solidification with diisopropyl ether (IPE) 75.6 g (yield: 78.3%) of a mixture (intermediate (12)) was obtained.

The synthetic route of 50397-74-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Raepto Co., Ltd.; Seok Mun-gi; Go Byeong-su; Im Cheol-su; Kim Hyeon-a; Kim Gyu-sik; Park Yong-pil; Han Gap-jong; Oh Yu-jin; (37 pag.)KR102059550; (2019); B1;,
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Adding a certain compound to certain chemical reactions, such as: 38487-85-3, name is 2-Amino-4-methoxybenzonitrile, 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 38487-85-3, Formula: C8H8N2O

EXAMPLE 28 9-Amino-3,4-dihydro-6-methoxyacridin-1(2H)-one 2-Amino-4-methoxybenzonitrile (7.51 g) was suspended in 75 ml of benzene containing 6.&sl0; g of cyclohexane-1,3-dione and 1.1 g of p -toluenesulfonic acid monohydrate. The reaction mixture was brought to reflux, at which time a homogeneous solution was obtained. After 15 minutes a thick precipitate developed, which was stirred in the refluxing solvent for an additional 15 minutes. At the end of this time thin layer chromatography (TLC, hereafter) showed that the starting material had been consumed, so the precipitate was filtered off, taken up in 2-butanone, and washed with sodium bicarbonate solution. The organic phase was dried and evaporated to a solid, which was triturated with ether to give 1&sl0;.61 g of the enamine, mp 194-196C. This material was suspended in 25&sl0; ml of tetrahydrofuran to which was then added 11.9 g of milled potassium carbonate and &sl0;.85 g of CuCl. The reaction mixture was then refluxed for a total of 48 hours, with additional portions of CuCl (&sl0;.5&sl0; g at a time) added at 6 hour and at 3&sl0; hour. At the end of this time methanol (1&sl0;&sl0; ml) was added to the reaction mixture and reflux was continued for 15 minutes. It was then filtered through diatomaceous earth, evaporated, and purified by flash chromatography (1&sl0;% methanol-dichloromethane). Obtained in this manner was 5.1 g of product that was suitable to be carried on to the next step. A 1.5 g portion was recrystallized from methanol to give 1.12 g of analytically pure material, mp 244-246C.

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; HOECHST-ROUSSEL, PHARMACEUTICALS INCORPORATED; EP179383; (1991); B1;,
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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 19179-31-8 as follows. category: nitriles-buliding-blocks

General procedure: 2-cyanopyridine (2.5g, 24.01mmol) was dissolved in EtOH (60mL) treated with K2CO3 (5.97g; 43.22mmol; 1.8 equiv) and H2NOH·HCl (3.0g; 43.22mmol; 1.8 equiv) and heated to reflux for 12h. The mixture was diluted with diethyl ether when it was cooled to room temperature. The product was collected by filtration, washed with water, and dried under an infrared lamp. The compound was used without further purification. Yield: 1.5g (45.5%).

According to the analysis of related databases, 19179-31-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xu, Li-Li; Wu, Yu-Feng; Wang, Lei; Li, Cui-Cui; Li, Li; Di, Bin; You, Qi-Dong; Jiang, Zheng-Yu; European Journal of Medicinal Chemistry; vol. 157; (2018); p. 1376 – 1394;,
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Adding a certain compound to certain chemical reactions, such as: 1483-54-1, name is 2-Amino-4-(trifluoromethyl)benzonitrile, 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 1483-54-1, Product Details of 1483-54-1

Potassium iodide (5.6 g, 34 mmol) and sodium nitrite (2.4 g, 35 mmol) were added to a solution of 2-amino-4-trifluoromethyl-benzonithle (2.58 g, 14 mmol) in acetonithle (60 ml_). The resultant mixture was cooled to 0 C in an ice-water bath with magnetic stirring. Ice-cold concentrated HCI (14 ml_) was added slowly drop-wise to the reaction mixture, causing the reaction mixture to become cloudy and deep red in color. The reaction mixture was stirred at 0 C for 30 minutes, then warmed to room temperature. Stirring at room temperature proceeded for 3 hours. The reaction mixture was poured into water, and the resulting suspension was extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered, and concentrated to give a purple liquid. A solution of this crude product and dichloromethane (200 ml_) was evaporated onto silica gel, and the dry silica gel-supported product was loaded onto a silica gel column. Manual flash chromatography using 5% ethyl acetate in hexanes afforded 2-iodo-4-trifluoromethyl-benzonithle as 3.58 g (87%) of a purple, crystalline solid.

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-Amino-4-(trifluoromethyl)benzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; FIROOZNIA, Fariborz; GILLESPIE, Paul; LIN, Tai-An; MERTZ, Eric; SIDDURI, Achyutharao; SO, Sung-Sau; TAN, Jenny; THAKKAR, Kshitij Chhabilbhai; WO2010/55005; (2010); A1;,
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Some common heterocyclic compound, 67515-59-7, name is 4-Fluoro-3-(trifluoromethyl)benzonitrile, molecular formula is C8H3F4N, 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. Product Details of 67515-59-7

A solution of 1.1 g (5.9 mmol) of 4-fluoro-3- trifluoromethylbenzonitrile and 485 mg (6.5 mmol) of [(S)- (+)-2-BUTANOL] in 10 mL of THE at-10 C was treated with 235 mg (5.9 mmol) of sodium hydride. The resulting mixture was stirred cold for 2 h, then quenched with 10 mL of [H2O.] The quenched solution was extracted with 30 mL [OF ET20,] dried over [MGS04] and concentrated. Chromatography on a Biotage 40M cartridge using 4: 1 v/v hexanes/EtOAc as the eluant afforded 550 mg of the title compound [: 1H] NMR (500 Mhz) [5] 0.99 (t, J=7.6, 3H), 1.35 (d, J=6.2, 3H), 1.58-1. 83 (m, 2H), 4.51 (septet, 1H), 7.04 (d, J=8.7, 1H), 7.75 (d, J=8.7, 1H), 7.85 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 67515-59-7, its application will become more common.

Reference:
Patent; Merck & Co., Inc.; WO2003/105771; (2003); A2;,
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Reference of 13338-63-1, A common heterocyclic compound, 13338-63-1, name is 3,4,5-Trimethoxyphenylacetonitrile, molecular formula is C11H13NO3, 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.

Method 1: Under a nitrogen atmosphere, in a glove box, Add 0.02 mmol of Pd2(dba)3·HCCl3 (tris(dibenzylideneacetone)dipalladium·chloroform), 0.04 mmol of tBuDavePhos. (2-di-tert-butylphosphonium-2-(N,N-dimethylamino)biphenyl) or 2-di-tert-butylphosphine-2′-(N,N-dimethylamino)-1,1′-biphenyl, 0.52 mmol of diphenylphosphine oxide, 1.5 equivalents of t-BuOK (potassium tert-butoxide), Adding to the Schlenk reaction tube in turn, then adding 0.4 mmol of 3,4,5-trimethoxybenzyl nitrile compound, vacuuming and backfilling with nitrogen; Under a nitrogen atmosphere, a solvent of 3 ml of 1,4-dioxane was added, and the reaction was continued at 120 C for 16 h. After the reaction is completed, it is cooled to room temperature and separated by column chromatography. The target product was obtained: 3,4,5-trimethoxybenzyldiphenylphosphine oxide in a yield of 96%.

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; Hunan University; Zhang Jishu; Qi Tafamingrenqingqiubugongkaixingming; (13 pag.)CN109438512; (2019); A;,
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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 935-02-4 as follows. Computed Properties of C9H5N

The mixture of phenol (0.1 g, 1.1 mmol), 3-phenylpropiolonitrile (0.13 g, 1.0 mmol), sodium carbonate (0.11 g, 1.0 mmol) in DMF (2 mL) was stirred at room temperature for 12 h. The reaction was monitored by TLC. After the completion of the reaction, the mixture was extracted with ethyl acetate (3×10 mL), and the liquor was washed with saturated brine (3×10 mL). The resulting organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to give product (0.22 g, 99% ). (Z)-3-Phenoxy-3-phenylacrylonitrile (3a)5 Colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.47 (d, J = 7.0 Hz, 2H), 7.34 (d, J = 7.2 Hz, 1H), 7.29 (d, J = 7.8 Hz, 2H), 7.23 – 7.18 (m, 2H), 7.01 (t, J = 7.4 Hz, 1H), 6.93 (d, J = 7.8 Hz, 2H), 5.32 (s, 1H). 13C NMR (150 MHz, CDCl3) delta 168.43, 155.72, 131.47, 129.75, 128.93, 126.92, 124.24, 118.16, 115.32, 115.09, 81.83. Anal. Calcd. for C15H11NO: C, 81.43; H, 5.01; N, 6.33. Found: C, 81.49; H, 4.99; N, 6.30.

According to the analysis of related databases, 935-02-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Du, Yan; Li, Zheng; Tetrahedron Letters; vol. 59; 52; (2018); p. 4622 – 4625;,
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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 868-54-2 as follows. Application In Synthesis of 2-Aminoprop-1-ene-1,1,3-tricarbonitrile

General procedure: A mixtureof 1 mmol of the corresponding aromatic aldehyde, 0.132 g (1 mmol) of malononitrile dimer, 0.125 g (0.2 mmol) of Triton X-100, and one drop of triethylamine in 5 mL of water was stirred at room temperature until the reaction was complete (TLC). The precipitate was ground with water, filtered off, washed with water, and recrystallized from propan-2-ol.

According to the analysis of related databases, 868-54-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ershov; Bardasov; Alekseeva, A. Yu.; Ievlev, M. Yu.; Belikov, M. Yu.; Russian Journal of Organic Chemistry; vol. 53; 7; (2017); p. 1025 – 1029; Zh. Org. Khim.; vol. 53; 7; (2017); p. 1014 – 1018,5;,
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Application of 50594-78-0,Some common heterocyclic compound, 50594-78-0, name is 5-Fluoro-2-nitrobenzonitrile, molecular formula is C7H3FN2O2, 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 2: 5-(4-Methylpiperazinyl)-2-nitrobenzenecarbonitrile 5-Fluoro-2-nitrobenzenecarbonitrile (1.02 equivalents) and N-methylpiperazine (1.0 equivalents) were dissolved in NMP. Triethylamine (2.1 equivalents) was added, and the resulting solution heated at 100 C. for 1 hour. The solution was cooled to room temperature and poured into H2O. A precipitate formed which was filtered to yield the desired product as a green solid. LC/MS m/z 247.3 (MH+), Rt 1.46 minutes.

The synthetic route of 50594-78-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CHIRON CORPORATION; US2005/256157; (2005); A1;; ; Patent; Chiron Corporation; US2005/261307; (2005); A1;,
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Adding a certain compound to certain chemical reactions, such as: 145689-34-5, name is 2-(2,3-Difluorophenyl)acetonitrile, 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 145689-34-5, Quality Control of 2-(2,3-Difluorophenyl)acetonitrile

Step 5: A stirred solution of 4-(5-difluoromethoxy-3-trifluoromethyl-pyrazol-1-yl)-benzaldehyde (40.5 mg, 0.13 mmol) and 2,3-difluorobenzylacetonitrile (20.3 mg, 0.13 mmol) in Ethanol (1 mL) was treated with 40% aqueous KOH (0.1 mL) at room temperature. The mixture was stirred for 1 hour. The resultant white precipitate was collected by filtration and washed with water to provide 5-difluoromethoxy-1-{4-[2-(2,3-difluoro-phenyl)-2-isocyano-vinyl]-phenyl}-3-trifluoromethyl-1H-pyrazole (30 mg, 51% yield) as a white solid: 1H-NMR (CDCl3) delta 6.39 (s, 1H), 6.62 (t, 1H, J=70.8 Hz), 7.14-7.28 (m, 2H), 7.36-7.42 (m, 1H), 7.65 (s, 1H), 7.80 (d, 2H, J=8.7), 8.02 (d,2H,J=8.7) ppm. ESMS calculated for C20H10F7N3O: 441.1; Found: 442.0 (M+H)+.

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; Chen, Shoujun; Ying, Weiwen; Jiang, Jun; Ono, Mitsunori; Sun, Lijun; US2005/272699; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts