Month: March 2021

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 34916-10-4 as follows. Formula: C7H9NO

To a stirred solution of R-06i-3 (4.00 g, 32.48 mmol) and KHMDS (1 .0 M, 42.87 mL, 42.87 mmol) in THF (200 mL) under N2at -78 C was added PhNTf2(14.85 g, 41 .57 mmol) and the reaction mixture was stirred at 20 C for 8 hours. Then, the mixture was cooled to 20 C and concentrated in reduced pressure at 40 C. The residue was poured into water and extracted with ethyl acetate. The combined organic phase was washed with brine, dried with anhydrous Na2S04, filtered and concentrated in vacuum. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate = 50/1 to 1 :1 ) to give R-06i- 4 (3.00 g, 36%) as a colorless oil. ESI-MS (M+1 ): 256.1 calc. for C8H8F3N03S: 255.0.

According to the analysis of related databases, 34916-10-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FUNDACION PARA LA INVESTIGACION MEDICA APLICADA; AGUIRRE ENA, Xabier; OYARZABAL SANTAMARINA, Julen; PROSPER CARDOSO, Felipe; RABAL GRACIA, Maria Obdulia; SAN JOSE ENERIZ, Edurne; SANCHEZ ARIAS, Juan Antonio; VILAS ZORNOZA, Amaia; (96 pag.)WO2018/229139; (2018); 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 1835-65-0 as follows. Product Details of 1835-65-0

General procedure: A 1.0 M solution of LiN(SiMe3)2 (2.2 mL, 2.2 mmol) in THF was added at -90 C in an argon atmosphere to a vigorously stirred solution of 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl (314 mg, 2.0 mmol) in absolute THF (30 mL). The reaction mixture was stirred at -90 C for 30 min. Then, a solution of tetrafluorophthalonitrile (400 mg, 2.0 mmol) in THF (5 mL) was added at -90 C under argon, stirring was continued, and the reaction was monitored by TLC (Silufol F254, EtOAc as an eluent). After 2 or 6 h, the cooling was stopped, the reaction mixture was allowed to warm up to room temperature and was brought into contact with air. Flash chromatography (SiO2, column 3 * 4 cm, EtOAc as an eluent) yielded dark brown solid mixture after solvent removal under reduced pressure at room temperature. The obtained solid mixture was separated by column chromatography (SiO2, column 3 * 20 cm, CH2Cl2 as an eluent), which afforded a dark green fraction of radical 1 and dark green fraction of radical 2. Both fractions were concentrated under reduced pressure to a volume of ~5 mL. Next, n-heptane (5 mL) was added, and the mixtures were kept at a temperature of 0-5 C for slow crystallization of radicals 1 and 2. 4.3. 2-(3,4-Dicyano-2,5,6-trifluorophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl (1) Yield 101 mg (15%); dark green crystals; mp 166.9 – 167.2 C (uncorrected). IR (KBr) max/cm-1: 430, 447, 474, 501, 542, 611, 629, 667, 694, 746, 781, 870, 899, 941, 955, 982, 1065, 1070, 1138, 1173, 1223, 1277, 1379, 1431, 1458, 1481, 1527, 1504, 1585, 1624, 1732, 2243 (C?N), 2569, 2631, 2854, 2928, 2947 3005, 3425; UV-vis (C2H5OH) lambdamax/nm (lg epsilon): 560 (2.37), 402 (3.32), 306 (4.21), 230 (4.19), 203 (4.45); UV-vis (KBr) lambdamax/nm: 425, 331, 307, 245, 233, 212; Anal. calcd for C15H12F3N4O2: C 53.42, H 3.59, F 16.90, N 16.61; found: C 53.50, H 3.25, F 16.97, N 16.74; HRMS: calcd. for C15H14F3N4O2 [M+] 337.0907; found 337.0912. 4.4. 2-(2-Amino-4,5-dicyano-3,6-difluorophenyl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazol-3-oxide-1-oxyl (2) Yield 134 mg (20%); dark green crystals; mp 179.5 – 179.8 C (uncorrected). IR (KBr) max/cm-1: 422, 436, 476, 501, 546, 615, 661, 673, 690, 761, 870, 895, 931, 947, 980, 1059, 1111, 1140, 1153, 1173, 1228, 1271, 1294, 1321, 1373, 1402, 1439, 1466, 1500, 1566, 1630, 1761, 2231 (CN), 2249 (CN), 2632, 2717, 2854, 2928, 2995, 3014, 3226, 3336; UV-vis (C2H5OH) lambdamax/nm (lg epsilon): 561 (2.58), 350 (3.92), 316 (4.08), 266 (4.41), 234 (4.33), 204 (4.16); UV-vis (KBr), lambdamax/nm: 401, 350, 269, 213, 211; Anal. calcd for C15H14F2N5O2: C 53.89, H 4.22, F 11.37, N 20.95; found: C 52.64, H 3.85, F 11.35, N 20.25; HRMS: calcd. for C15H14F2N5O2 [M+] 334.1110; found 334.1108.

According to the analysis of related databases, 1835-65-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fedyushin, Pavel; Panteleeva, Elena; Bagryanskaya, Irina; Maryunina, Kseniya; Inoue, Katsuya; Stass, Dmitri; Tretyakov, Evgeny; Journal of Fluorine Chemistry; vol. 217; (2019); p. 1 – 7;,
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Electric Literature of 453565-55-4, 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. 453565-55-4, name is 5-Fluoroisophthalonitrile, This compound has unique chemical properties. The synthetic route is as follows.

5-Morpholinoisophthalonitrile.; A mixture of 5-fluoroisophthalonitrile (1.00 g, 6.84 mmol, 1.0 eq.), morpholine (1192 mul, 13.69 mmol, 2.0 eq.), and DMSO (2.0 ml) was stirred overnight at 500C. The mixture was diluted with 2% aq. HCl (30 ml), the solid was separated by filtration, washed with 2% aq. HCl, water, and dried in HV to give pure target product (white solid, 1.35 g, 92% yield, 99% pure by LCMS – no mass observed). 1H-NMR (DMSO-d6) delta (ppm) 7.69 (s, 3H), 3.71 (m, 4H), 3.28 (m, 4H).

The chemical industry reduces the impact on the environment during synthesis 5-Fluoroisophthalonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KEMIA, INC.; WO2008/21388; (2008); A1;,
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Some common heterocyclic compound, 1897-41-2, name is 2,3,5,6-Tetrachloroterephthalonitrile, molecular formula is C8Cl4N2, 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: 2,3,5,6-Tetrachloroterephthalonitrile

0.60g (0.015 mol) of sodium hydroxide was added to a solution of 1.22g(0.0075 mol) of 3,5-dichloropyridin-4-amine in 40 mL of DMF, followed by addition of 2g (0.0075 mol) of 2,3,5,6-tetrachloroterephthalonitrile under stirring,the mixture was stirred for 5 h after addition at room temperature. After the reaction was over by Thin-Layer Chromatographymonitoring, the reaction mixture was poured into water and extracted with ethyl acetate, the organic phasewas washed with water and saturated brine, dried over anhydrous magnesium sulfate, filtered and then concentratedunder reduced pressure. The residue was purified through silica column (ethyl acetate/petroleum ether (boiling pointrange 60-90¡ãC) = 1:3, as an eluent) to give 2.16 g of compound C-124 as yellow solid, m.p. 202-204¡ãC.[0132] 1H-NMR (300MHz, internal standard TMS, solvent CDCl3) delta(ppm): 7.28(br, 1H, NH), 8.30(s, 2H, Py-2,6-2H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1897-41-2, its application will become more common.

Reference:
Patent; Sinochem Corporation; Shenyang Research Institute of Chemical Industry Co., Ltd.; LIU, Changling; HUANG, Guang; LAN, Jie; HAO, Shulin; LI, Zhinian; LI, Huichao; GUAN, Aiying; JIANG, Airu; XU, Ying; EP2757092; (2014); A1;,
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13531-48-1, name is Methyl 3-cyanobenzoate, 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. HPLC of Formula: C9H7NO2

General procedure: To a solution of cyanide (8.0 mmol) in 20 mL ethanol was added hydroxylamine (solution 50% in water) (4.0 mL) at room temperature. Thereaction mixture was stirred atreflux for 3 to 4 hours until the nitriles were completed converted(monitored by TLC). The mixture solution was evaporated and extracted withdichloromethane (10 mL¡Á3). The combined organic layers were washed with brine(10 mL), dried over anhydrous Na2SO4, filtered andconcentrated to give the crude product, which was further purified by columnchromatography to afford compounds 4and 8.

The synthetic route of 13531-48-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Mei; Li, Shan; Ai, Jing; Sheng, Rong; Hu, Yongzhou; Hu, Youhong; Geng, Meiyu; Bioorganic and Medicinal Chemistry Letters; vol. 26; 23; (2016); p. 5679 – 5684;,
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Application of 621-03-4, 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. 621-03-4, name is 2-Cyano-N-phenylacetamide, This compound has unique chemical properties. The synthetic route is as follows.

Cyanoacetic acid (0.96 g, 11.1 mmol, 1 eq) was added to a mixture of PC15 (2.35 g, 11.1 mmol, 1 eq) in 200 mL of CH2C12, and the mixture refluxed for 30 minutes. After cooling, aniline (1.01 mL, 1.03 g, 11.1 mmol) was added and the solution was refluxed for 2hrs. The reaction mixture was allowed to cool to room temperature, and then concentrated to dryness at the rotary evaporator. A 50 mL portion of water was added and the suspension was filtered. The resulting solid was then washed with 25 mL of 1.0 N NaHC03 solution, 25 mL of water and then dried to afford the desired cyanoamide as a white amorphous solid (1.64 g, 92%). This solid was of sufficient purity to be used without further purification in the subsequent reaction. 1H NMR (400 MHz, acetone-d6) delta 9.58 (s, 1H), 7.62 (d, / = 8.4 Hz, 2H), 7.33 (t, / = 8.0 Hz, 2H), 7.11 (t, / = 7.2 Hz, 1H), 3.82 (s, 2H).A 0.9 g portion (12.8 mmol, 1.25 eq) of NH2OH HCl was added to Na2C03 (1.36 g, 12.8 mmol, 1.25 eq) dissolved in 5 mL of water, and the solution was diluted with 50 mL of methanol. The cyanoamide from the previous step (1.64 g, 10.2 mmol) was added and the mixture was refluxed for 2 hours. After cooling, the reaction mixture was concentrated in vacuo, and the resulting solid was mixed with a hot 3:1 mixture of ethyl acetate:hexane. The insoluble material was immediately removed by filtration, and the filtrate was concentrated to dryness at the rotary evaporator. The solid residue was purified by column chromatography (silica gel, ethyl acetate: methanol 20:1) and recrystallized to afford Example 1 as a white crystalline solid (0.67 g, 34%). 1H NMR (400 MHz, acetone-d6) delta 9.53 (s, 1H), 8.70 (s, 1H), 7.65-7.63 (m, 2H), 7.31-7.27 (m, 2H), 7.07-7.04 (m, 1H), 5.39 (s, 2H), 3.17 (s, 2H).

The chemical industry reduces the impact on the environment during synthesis 2-Cyano-N-phenylacetamide. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE JOHNS HOPKINS UNIVERSITY; CASERO, Robert, A.; BYTHEWAY, Ian; WOSTER, Patrick, M.; WO2012/34116; (2012); A2;,
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Synthetic Route of 612-24-8, A common heterocyclic compound, 612-24-8, name is 2-Nitrobenzonitrile, molecular formula is C7H4N2O2, 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: Nitrobenzene (0.6mmol), 5wt% Pd/C (0.5mmol %, 0.003mmol), H2O (10 equiv, 6.0mmol), B2(OH)4 (3.3 equiv, 2.0mmol), and CH3CN (1.0mL) were added in a 10mL tube. The reaction mixture was stirred at 50C for 24h. When the reaction was complete monitored by TLC, the mixture was cooled to room temperature. Water (5mL) was added, and extracted with EtOAc (3¡Á5mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give aniline 2a (55mg, 99%).

The synthetic route of 612-24-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Yanmei; Zhou, Haifeng; Liu, Sensheng; Pi, Danwei; Shen, Guanshuo; Tetrahedron; vol. 73; 27-28; (2017); p. 3898 – 3904;,
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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. 90433-20-8, name is 2-(3-Bromophenyl)-2-methylpropanenitrile, A new synthetic method of this compound is introduced below., Product Details of 90433-20-8

Step 2. A solution of 2-(3-bromo-phenyl)-2-methyl-propionitrile [0.5 g, 2.2 mmol, Intermediate (65)] in toluene (8 mL) and THF (2 mL) is added triisopropyl borate (0.61 mL, 2.68 mmol) at -780C. tert- Butyl lithium (1.7 M in pentane, 1.55 mL, 2.68 mmol) is added dropwise during 15 min. Reaction mixture is stirred at -78C for additional 1 hour, warmed up to -2O0C and quenched with 2N hydrochloric acid (10 mL). The reaction mixture is extracted with ether, combined ether layers are washed with brine, dried and concentrated to obtain 3-fcyano-dimethyl-methyl’)-phenyl boronic acid (0.5 g) [Intermediate (66)] as an oil.

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; AVENTIS PHARMACEUTICALS INC.; WO2006/44732; (2006); A2;,
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Adding a certain compound to certain chemical reactions, such as: 78473-00-4, name is 4-Amino-3,5-dichlorobenzonitrile, 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 78473-00-4, Product Details of 78473-00-4

EXAMPLE 17 2-Ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (2,6-dichloro-4-cyanophenyl)amide Starting from 2-ethyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (0.10 g) and 4-amino-3,5-dichlorobenzonitrile (0.12 g). Purification by column chromatography on silica with 20% then 30% then 50% ethyl acetate in hexane to give the title compound (0.051 g) as a cream solid. TLC Rf 0.125 (20% ethyl acetate in hexane)

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; Darwin Discovery, Ltd.; US6169090; (2001); A;,
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67832-11-5, name is 4-Bromo-2-methylbenzonitrile, 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. Quality Control of 4-Bromo-2-methylbenzonitrile

Example 1: Synthesis of 4-{4-{1-hydroxyethyl)pyridin-3-yl)-2-methylbenzonitrileStep 1: 2-methyl-4-(4,4,5l5-tetramethyl-1 ,3 2-dioxaborolan-2-yl)benzonitrile (1a)A mixture of 4-bromo-2-methylbenzonitrile (1 g, 5.10 mmol), bis(pinacolato)diboron (1.554 g, 6.12 mmol), potassium acetate (1.001 g, 10.20 mmol) and PdCI2(dppf).CH2CI2 adduct (0.208 g, 0.255 mmol) in 1 ,4-Dioxane (12.75 ml) was heated to 80 C for 5 hr. The mixture was concentrated, and the residue was purified via Biotage (0-10% EtOAc/heptane; SNAP50 column) giving compound 1 as white solid (860 mg, 69%). 1H NMR (400 MHz, CDCI3) delta ppm 1.28 (s, 12 H) 2.38 – 2.52 (m, 3 H) 7.51 (d, J=7.64 Hz, 1 H) 7.55 – 7.64 (m, 1 H) 7.67 (s, 1 H).

The synthetic route of 67832-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ALLAN, Martin; CHAMOIN, Sylvie; HU, Qi-Ying; IMASE, Hidetomo; PAPILLON, Julien; WO2011/61168; (2011); A1;,
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