Tag: M.W=200-300

These common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, 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. Formula: C14H10N2O2

To a mixture of 3-(2-aminoethyl)-1-(4-chlorobenzyl)-6-(3-fluoro-4-isopropoxyphenylimino)-1,3,5-triazinane -2,4-dion hydrochloride (200 mg, 0.413 mmol) and ethyl ether (8 mL) were added triethylamine (0.126 mL, 0.908 mmol) and diphenyl-N-cyanocarbonimidate (216 mg, 0.908 mmol), and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 1-(4-chlorobenzyl)-6-(3-fluoro-4-isopropoxyphenylimino)-3-(4-cyanoimino-4-phenoxy-3-aza butyl)-1,3,5-triazinane-2,4-dion (170 mg, Yield: 70%) as colorless solid. 1H-NMR (delta ppm TMS/CDCl3): 1.40 (6H, d, J=6.0 Hz), 3.70 (2H, m), 4.07 (2H, m), 4.49 (1H, sept, J=6.0 Hz), 5.17 (2H, s), 6.47-6.61 (1H, m), 6.94 (1H, t, J=8.7 Hz), 7.16-7.20 (4H, m), 7.30-7.46 (4H, m), 7.79 (1H, m), 8.25 (1H, s).

The synthetic route of Diphenyl N-cyanocarbonimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; KAMEYAMA, Takayuki; HORIGUCHI, Tohru; ASAHI, Kentaro; ENDOH, Takeshi; FUJII, Yasuhiko; SHINTANI, Takuya; NAKAMURA, Ken’ichiroh; JIKIHARA, Sae; HASEGAWA, Tsuyoshi; OOHARA, Miho; TADA, Yukio; MAKI, Toshikatsu; IIDA, Akira; EP2604595; (2013); A1;,
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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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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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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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Adding a certain compound to certain chemical reactions, such as: 1835-49-0, name is Tetrafluoroterephthalonitrile, 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 1835-49-0, Product Details of 1835-49-0

Dry tetrafluoroterephthalonitrile 51.02 g (98% pure, 50.0 g in terms of tetrafluoroterephthalonitrile), dry 5% Pd/C 1.0 G, Zeolite 4A powder 37. 5 g (Molecular Sieve 4A produced by Union Showa K. K. ), and toluene 200.0 g were introduced into a 500 ml stainless steel autoclave (NU-4 model produced by Nitto Koatu Co., Ltd. ), and the autoclave was purged with nitrogen. Thereafter the contents were heated to 160C under stirring, and hydrogen pressurized at a pressure higher than that in the autoclave at the above temperature by 0.1 MPa was supplied to initiate hydrogenolysis. The rate of hydrogen absorption lowered in 2 hours after the hydrogen supply was initiated, so that the pressure in the autoclave was raised by 0. 05 MPa with hydrogen.The supply of hydrogen was terminated when the hydrogen absorption was achieved at 125 mol% (based on the mol of tetrafluoroterephthalonitrile under standard conditions). The above reaction was completed in 8 hours. Cooled to room temperature, the reaction slurry was filtered, and the filtrate was analyzed with the gas chromatography analyzer. The analysis gave a conversion of 98. 0% and a reaction yield of 78. 0% (product: 2,3, 5,6-tetrafluorobenzonitrile). The solvent of the above reaction solution was removed by means of an evaporator, and the residue was distilled under reduced pressure to obtain 2,3, 5, 6-tetrafluorobenzonitrile as a fraction under 50 mmHg at 88C.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Tetrafluoroterephthalonitrile, and friends who are interested can also refer to it.

Reference:
Patent; SHOWA DENKO K.K.; WO2004/9535; (2004); A1;,
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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. 20099-89-2, name is 4-(2-Bromoacetyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 20099-89-2

Step-I: 4-(2-amino-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidin-6-yl)benzonitrile (XI-10-I) A mixture of 2,6-diaminopyrimidin-4-ol (1 g, 7.93 mmol) and NaOAc (0.846 g, 10.31 mmol) in water (180 mL) was heated to 100 C. for 20 minutes. To this was added a suspension of 4-(2-bromoacetyl)benzonitrile (2.2 gm, 8.73 mmol) [prepared according to procedure mentioned in J. Med. Chem., 2011, 54(12), 4042-4056] in MeOH (25 mL) and heated overnight at 100 C. After completion of reaction, the reaction mixture was cooled to 0 C. Resultant solid product was filtered off and dried under reduced pressure to provide title compound XI-10-I (1.2 g, 100%). LCMS: m/z 252 (M+1)+.

According to the analysis of related databases, 20099-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Thakkar, Mahesh; Koul, Summon; Bhuniya, Debnath; Mookhtiar, Kasim; Kurhade, Santosh; Munot, Yogesh; Mengawade, Tanaji; Kulkarni, Bheemashankar A.; US2015/64196; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 867366-91-4, name is 3-Bromo-5-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 867366-91-4, SDS of cas: 867366-91-4

Step 2 A solution of 3-bromo-5-methoxybenzaldehyde (4.02 g, 18.7 mmol) and hydroxylamine hydrochloride (6.50 g, 93.5 mmol) in pyridine (50 ML) and EtOH (50 ML) was heated to 65 C. for 16 h.The solvent was removed, and the remaining materials were partitioned between 1:1 EtOAc/hexanes (150 ML) and H2O (75 ML).The organic layer was washed with brine (60 ML), and the solvents were evaporated.The remaining oil was dissolved in anhydrous dioxane (50 ML), and trifluoroacetic anhydride (5.1 ML, 37.4 mmol) and pyridine (9.07 ML, 112.2 mmol) were added.The mixture was heated to 60 C. for 3 h and then cooled to RT. CHCl3 (100 ML) was added, and the organic layer was washed with H2O (2*50 ML), 5% aqueous HCl solution (30 ML), brine (30 ML), and dried with anhydrous MgSO4.The solvents were removed to provide a white solid.This solid was placed in a 150 ML flask that was flushed with nitrogen.Collidine (40 ML) and LiI (7.92 g, 59.10 mmol) were added, and the mixture was heated to 180 C. for 5 h.The reaction mixture was cooled to RT, and partitioned between H2O (400 ML) and EtOAc (100 ML).The layers were separated, and the aqueous layer was acidified with 10% aqueous HCl solution, and extracted with 2:1 EtOAc/hexanes (3*125 ML).The combined organic layers were washed with H2O (100 ML), 10% aqueous HCl solution (2*50 ML), brine (75 ML), and dried with anhydrous MgSO4.The solvents were evaporated and the resulting solid was purified by flash chromatography on silica gel (10% to 40% EtOAc/hexanes) to provide 3.40 g (92%) of 3-bromo-5-hydroxybenzonitrile (116)116).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromo-5-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; Roche Palo Alto LLC; US2004/198736; (2004); A1;,
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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. 101184-73-0, name is 2-(4-Bromophenyl)-2-methylpropanenitrile, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 101184-73-0

A suspension of 2-(4-bromophenyl)-2-methylpropanenitrile (110 mg, 0.491 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (187 mg, 0.736 mmol), potassium acetate (72.3 mg, 0.736 mmol) and Pd(dppf)Cl2 (18.0 mg, 0.0250 mmol) in dioxane (3 mL) was degassed and the reaction was heated to 95 C. for 90 minutes. The reaction mixture was concentrated to provide 2-methyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanenitrile which was used directly in subsequent reactions.

According to the analysis of related databases, 101184-73-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Gilead Scientific Systems, Inc.; Cory, Kevin S; Doo, Jimin; Farrand, Julie; Guerrero, Juan A; Katana, Ashley A; Cato, Daryl; Laisaweed, Scott I; Lee, Jiayao; Lingco, John O; Nicolaus, May; Notte, Gregory; Phyen, Hyeoung-Jung; Sangy, Michael; Sumit, Arun C; Adam J, Surayyah; Stephens, Cork L; Venkatraman, Chandrasekar; Watkins, William J; Yang, Jong Yu; Jabloki, Jeff; Jifel, Shiela; Ro, Jennifer; Lee, Sung H; Jao, Chung Dong; Grove, Jeffery; Su, Jianjun; Blomgren, Peter; Mitchell, Scott A; Shyung, Jin Ming; Chandrasekar, Jayaraman; (460 pag.)KR2016/37198; (2016); A;,
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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. 1735-53-1, name is 4-Bromo-3-(trifluoromethyl)benzonitrile, A new synthetic method of this compound is introduced below., Recommanded Product: 1735-53-1

Description for D664-(1 -Cyclohexen-1 -yl)-3-(trifluoromethyl)benzamide (D66)4-bromo-3-(trifluoromethyl)benzonitrile (commercial) (1.2 g, 4.80 mmol), 1- cyclohexen-1-ylboronic acid (0.907 g, 7.20 mmol), sodium methoxide (0.778 g, 14.40 mmol) and bis(triphenylphosphine)palladium(ll) chloride (0.337 g, 0.480 mmol) were added to dry methanol (12 ml.) and the mixture heated in the microwave at 80 0C for 10 minutes. The reaction mixture was partitioned between ethyl acetate (40 ml.) and water (40 ml.) and then the organic phase washed with further water (40 ml_). The organic phase was dried (MgSC^), filtered and the solvent removed in vacuo. The crude product was purified by flash silica chromatography, eluting with 0-75 % ethyl acetate in hexane to give the title compound as a white solid (1.02 g). deltaH (CDCI3, 400 MHz): 8.09 (1 H, m), 7.90 (1 H, dd), 7.32 (1 H, d), 6.3-5.8 (2H, m) 5.61 (1 H, s), 2.25-2.13 (4H, m), 1.80-1.60 (4H, m). MS (ES): C14H14F3NO requires 269; found 270 (MH+).

The synthetic route of 1735-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2008/74821; (2008); A1;,
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Electric Literature of 1953-99-7, A common heterocyclic compound, 1953-99-7, name is 3,4,5,6-Tetrachlorobenzene-1,2-dicarbonitrile, molecular formula is C8Cl4N2, 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.

Synthesis Example 6: Synthesis of 3,4,6-trichloro-5-(2-bromo-phenoxy)-phthalonitrile 5 g of 3,4,5,6-tetrachlorophthalonitrile, 3.25 g of 2-bromophenol, 3.9 g of K2CO3, and 25 ml of N,N-dimethyl formamide were put in a 100 ml flask, and then stirred while heated at 70¡ã C. When the reaction was complete, EA (ethyl acetate) was used for an extraction. After the extraction, the resultant was concentrated to obtain a solid. Herein, the obtained solid was dissolved in an small amount of dichloromethane, several times washed with hexane, filtered, and vacuum-dried to obtain 3,4,6-trichloro-5-(2-bromo-phenoxy)-phthalonitrile.

The synthetic route of 1953-99-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SAMSUNG SDI CO., LTD.; JEONG, Euisoo; SEO, Hyewon; SHIN, Myoungyoup; SHIN, Sunwoong; JUNG, Juho; HAN, Gyuseok; (25 pag.)US2018/335547; (2018); A1;,
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