Month: April 2021

Reference of 874-97-5, 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. 874-97-5, name is 3-Cyanobenzyl alcohol belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Procedure 2: In a vial the acid (1.32 mmol), dicyclohexylcarbodiimide (DCC; 1.45 mmol) and the alcohol (1.32 mmol) were dissolved in dry THF (5mL). The reaction mixture was stirred at room temperature overnight, and then filtered. The filtrate was diluted with dichloromethane and washed with water (2x) followed by brine, dried over sodium sulfate and concentrated to a crude residue, which was purified by flash chromatography.

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, 3-Cyanobenzyl alcohol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Titchenell, Paul M.; Hollis Showalter; Pons, Jean-Francois; Barber, Alistair J.; Jin, Yafei; Antonetti, David A.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 10; (2013); p. 3034 – 3038;,
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17983-30-1, name is 3-Oxocyclohexanecarbonitrile, 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. Safety of 3-Oxocyclohexanecarbonitrile

Example 2Conversion of 3-cyanocyclohexanone to 3-aminomethyl-1-cyclohexylamineThe apparatus used consisted of 8 tubular reactors connected in series. The dimensions of the first two tubes (C1-C2) were 1500¡Á6¡Á1 mm. The dimensions of the 6 further tubes (C3-C8) were 2000¡Á8¡Á1.5 mm. The first two reactors (C1-C2) were charged with 15.7 g of TiO2 extrudates with a diameter of 1.5 mm, the remaining 6 reactors each with approx. 85 g of a hydrogenation catalyst (Mn3O4 5-6.2%, Na2O 0-0.5%, H3PO4 2.8-3.8%, remainder Co+CoO) which had been reduced with hydrogen at 280 C. at a pressure of 1 bar for 24 hours.The temperature of the first two reactors C1-C2 was adjusted to 60 C. The temperature of reactors C3-C4 was 90 C., the temperature of reactors C5-C6 was 115 C. and the temperature of reactors C7-C8 was set to 130 C. Between reactors C2 and C3, hydrogen was fed into the reaction mixture under pressure. The operating pressure was 230 bar.23 g/h of a mixture of THF and 3-cyanocyclohexanone in a ratio of 1:1 together with 73 g/h of NH3 were pumped into the first reactor (C1), and 17 standard liters/h of hydrogen were also fed in upstream of reactor C3. The reaction output was decompressed through a regulating valve. In a downstream phase separator, hydrogen was then removed and ammonia was evaporated off.A total of 592 g of 3-cyanocyclohexanone were used. The crude output was distilled through a 60 cm column with random packing at <1 mbar. The product distilled over at 54 C. 433.7 g of 3-aminomethyl-1-cyclohexylamine were obtained as a mixture of cis/trans isomers with a purity of 99.5% (cis: 85.6, trans: 14.1; CT ratio: 86:14). The yield in the hydrogenation stage was 84% including the product content in the different fractions and 70.4% of pure product after the distillation.The mixture of the isomeric diamines was characterized by GC-MS, NMR and elemental analysis.13C-NMR (125 MHz, DMSO): 50.33 (cis-AMCHA), 48.57 (cis-AMCHA), 47.22 (trans-AMCHA), 45.35 (trans-AMCHA) 41.26 (cis-AMCHA), 40.43 (cis-AMCHA), 38.02 (trans-AMCHA), 36.88 (cis-AMCHA), 35.03 (trans-AMCHA), 34.53 (trans-AMCHA), 29.87 (cis-AMCHA), 29.44 (trans-AMCHA), 24.61 (cis-AMCHA), 19.66 (trans-AMCHA).In the GC-MS, by the method of 30m db35 MS 0.25 micrometer, start temperature 60 C., temperature ramp 5 C./min to 280 C. and bakeout at this temperature for 30 min, two main peaks were detected, retention times 19.07 min (85.6 area %) and 19.2 min (14.1 area %).The following fragment distributions were obtained (M+=128 corresponds to the particular molecular peak):Peak 1:m/z (%)=18(5), 27(5), 28(14), 29(7), 30(59), 39(9), 41(15), 42(13), 43(48), 44(17), 53(5), 54(12), 55(11), 56(100), 57(15), 58(9), 67(23), 68(11), 69(17), 70(18), 71(3), 77(4), 79(6), 80(3), 81(9), 82(28), 83(9), 85(4), 94(3), 96(8), 98(79), 99(36), 110(6), 111(19), 112(3)Peak 2:m/z (%)=18(4), 27(6), 28(14), 29(7), 30(61), 39(10), 41(16), 42(15), 43(45), 44(12), 53(6), 54(11), 55(11), 56(100), 57(32), 58(9), 67(20), 68(11), 69(20), 70(18), 71(3), 77(4), 79(7), 80(3), 81(9), 82(25), 83(14), 84(3), 85(3), 94(3), 96(10), 98(68), 99(22), 110(7), 111(41), 112(5)To determine the elemental analyses, an Elementar Vario EI III automatic analyzer was used.The elemental analysis gave_C=64.8 (expected: 65.6); N=22.1 (expected: 21.9); H=12.8 (expected: 12.6) g/100 g The synthetic route of 17983-30-1 has been constantly updated, and we look forward to future research findings. Reference:
Patent; BASF SE; US2011/124919; (2011); A1;,
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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. 115661-37-5, name is 2-Amino-3-fluorobenzonitrile belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 115661-37-5

To a mixture of 2-amino-3-fluorobenzonitrile (41.9 g), sodium acetate (30.3 g) and toluene (200 mL) was added diketene (28.2 mL) over 10 min at 0C. The reaction mixture was stirred at room temperature for 7 hr. To the reaction mixture were added toluene (150 mL) and diketene (4.7 mL) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether/ethanol to give the title compound (48.64 g). MS (ESI+): [M+H]+ 221.2

The synthetic route of 115661-37-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Pharmaceutical Company Limited; NAGAMIYA, Hiroyuki; YOSHIDA, Masato; SETO, Masaki; MARUI, Shogo; ODA, Tsuneo; ISHICHI, Yuji; SUZUKI, Hideo; KUSUMOTO, Tomokazu; YOGO, Takatoshi; RHIM, Chul Yun; YOON, Cheolhwan; LEE, Gil Nam; KANG, Hyun Bin; KIM, Kwang Ok; JEON, Hye Sun; EP2818473; (2014); A1;,
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Reference of 501420-63-9,Some common heterocyclic compound, 501420-63-9, name is 2-(3-Bromo-4-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, 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.

(3-Bromo-4-fluorophenyl)acetonitrile (4.00 g, 18.32 mmol), bis(pinacolato)diboron (5.22 g, 20.15 mmol), potassium acetate (55.86 mmol) and bis(triphenylphosphine)palladium(II) chloride (15.2% of Pd) (393.53 mg, 0.55 mmol) were dissolved in oxygen-free 1,4-dioxane (40 ml, max. 0.005% of water) under argon. The reaction mixture was subsequently heated at a temperature of 130 C. for 90 min. When the reaction conversion was complete, the mixture was filtered through kieselguhr. The filtrate was diluted with dichloromethane (200 ml) and water (50 ml) and extracted. The organic phase was dried over sodium sulfate, subsequently filtered and evaporated to dryness in vacuo, giving [4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetonitrile as oil (7.59 g, purity 81%, MS: 262.2 [M+H+]), which was reacted further without further work-up.

The synthetic route of 501420-63-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck Patent GmbH; FUCHSS, Thomas; EMDE, Ulrich; BUCHSTALLER, Hans-Peter; MEDERSKI, Werner; (224 pag.)US2016/83401; (2016); A1;,
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Related Products of 79463-77-7, A common heterocyclic compound, 79463-77-7, name is Diphenyl N-cyanocarbonimidate, molecular formula is C14H10N2O2, 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 122 (100 mg, 0.27 mmol) was dissolved in isopropanol (5 mL) and DIPEA (52.7 mg, 0.41 mmol) and diphenyl N-cyanocarbonimidate [79463-77-7] (79.7 mg, 0.32 mmol) were added. The reaction mixture was stirred at r.t. for ~1 h. p-Toluidine [106-49-0] (31.9 mg, 0.30 mmol) was added and the reaction mixture was stirred at r.t for ~4 h. The reaction mixture was heated at 80 C for 30 minutes. The precipitate was filtered, washing with isopropanol and Et20 to afford the title compound (70 mg, 0.15 mmol, 54%). LCMS [M+H]+478.2, [M+Na]+ 500.2, RT 2.174 minutes, 100.0% purity (Method 1).

The synthetic route of 79463-77-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UCB BIOPHARMA SRL; CHOVATIA, Prafulkumar Tulshibhai; CONNELLY, Rickki Lee; FRANKLIN, Richard Jeremy; HASLETT, Gregory William; HENRY, Alistair James; MADDEN, James; NEUSS, Judi Charlotte; NORMAN, Timothy John; PHILPS, Oliver; PITT, William Ross; RAMPALAKOS, Konstantinos; SELBY, Matthew Duncan; SELVARATNAM, Suganthan; TRANI, Giancarlo; ZHU, Zhaoning; (768 pag.)WO2019/243550; (2019); A1;,
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Related Products of 939-79-7, The chemical industry reduces the impact on the environment during synthesis 939-79-7, name is 4-Methyl-3-nitrobenzonitrile, I believe this compound will play a more active role in future production and life.

Furan-2,5-dicarboxaldehyde (197mg, 1.6mmol) and 4-cyano-2-nitrotoluene (12; 600mg, 3.7mmol) were dissolved in sulfolane (1mL) to which was added piperidine (200 muL, 2.0mmol). The mixture was heated to 150C in a sealed tube for 30min, producing a dark suspension. The reaction was cooled to room temperature, and MeOH (5mL) and Et2O (5mL) were added. The solids were triturated, filtered, rinsed with Et2O, and dried to yield 417mg (64%) of product as a brown powder. Material is too insoluble for 1H NMR evaluation.

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, 4-Methyl-3-nitrobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Williams, John D.; Nguyen, Son T.; Gu, Shen; Ding, Xiaoyuan; Butler, Michelle M.; Tashjian, Tommy F.; Opperman, Timothy J.; Panchal, Rekha G.; Bavari, Sina; Peet, Norton P.; Moir, Donald T.; Bowlin, Terry L.; Bioorganic and Medicinal Chemistry; vol. 21; 24; (2013); p. 7790 – 7806;,
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Reference of 1255870-63-3, A common heterocyclic compound, 1255870-63-3, name is 4-Bromo-2-ethoxybenzonitrile, molecular formula is C9H8BrNO, 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.

A suspension of 4-bromo-2-ethoxybenzonitrile (1.50 g, 6.5 mmol), hydroxylamine hydrochloride (913 mg, 13 mmol) and NaHCOs (1.365 g, 16.3 mmol) in water (1.32 mL) and EtOH (26.6 mL) is stirred in a sealed tube at 90C for 6h. Once at RT, the product precipitated from the RM upon addition of water. The solid is filtered off under high vacuum, washing with water and some EfeO. A first crop of pure title compound (947 mg) was thus obtained as white solid. The filtrate is extracted with EtOAc. The organic layer is then washed twice with brine, dried over MgS04, filtered and concentrated. The residue is purified by FC (hept/EtOAc 1 :1) to yield another crop of the pure title compound as a white solid (448 mg), merged with the first batch from precipitation. The title compound is obtained as a white solid (1.395 g, 83%). LC-MS B: tR = 0.53min, [M+H]+ = 259.12.

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; IDORSIA PHARMACEUTICALS LTD; BOSS, Christoph; CORMINBOEUF, Olivier; FRETZ, Heinz; LYOTHIER, Isabelle; POZZI, Davide; RICHARD-BILDSTEIN, Sylvia; SIENDT, Herve; SIFFERLEN, Thierry; (223 pag.)WO2018/210994; (2018); 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. 610-66-2, name is 2-(2-Nitrophenyl)acetonitrile, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 2-(2-Nitrophenyl)acetonitrile

General procedure: To a solution of the correspongding catalyst 4k (5 mol%), K2CO3 (2 equiv) and 2-(2-nitrophenyl)acetonitrile (0.10 mmol) in CH2Cl2 (1.0 mL), and then was cooled to -20 C before the imines (0.12 mmol) was introduced. When the reaction was finished (determined by TLC analysis), the crude mixture was warmed to room temperature and purified by flash column chromatography (silica gel: petroleum ether/AcOEt = 5:1) to afford the products

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 610-66-2.

Reference:
Article; Pan, Renming; Zhang, Jiaxing; Zheng, Changwu; Wang, Hongyu; Cao, Dongdong; Cao, Weiguo; Zhao, Gang; Tetrahedron; vol. 73; 17; (2017); p. 2349 – 2358;,
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68119-31-3, name is 2-(2,2-Difluorobenzo[d][1,3]dioxol-5-yl)acetonitrile, 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: C9H5F2NO2

Sodium hydroxide (50% aqueous solution, 10 mL) was slowly added to a mixture of crude (2,2-difluoro-benzo[l,3]dioxol-5-yl)-acetonitrile, benzyltriethylammonium chloride (3.00 g, 15.3 mmol), and l-bromo-2-chloroethane (4.9 g, 38 mmol) at 70 0C.[00171] The mixture was stirred overnight at 70 0C before the reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and evaporated to dryness to give crude l-(2,2-difluoro-benzo[l,3]dioxol-5- yl)-cyclopropanecarbonitrile, which was used directly in the next step.

The synthetic route of 68119-31-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; RUAH, Sara, Hadida, S.; GROOTENHUIS, Peter, D., J.; VAN GOOR, Fredrick; MILLER, Mark, T.; MCCARTNEY, Jason; ZHOU, Jinglan; BEAR, Brian; NUMA, Mehdi, Michel, Djamel; WO2010/53471; (2010); 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. 5332-06-9, name is 4-Bromobutanenitrile, A new synthetic method of this compound is introduced below., Product Details of 5332-06-9

Dissolve ethyl imidazole-2-carboxylate (200 mg, 1.43 mmol) in 5 ml of N,N-dimethylformamide, add cesium carbonate (931 mg, 2.85 mmol) for 0.5 h, and add 4-bromobutyronitrile (317 mg , 2.14mmol), warmed to 80 for 2h, the reaction was completed by TLC, stopped the reaction, cooled to room temperature, diluted with water, extracted with ethyl acetate (3¡Á20ml), combined organic layers, washed with saturated brine, anhydrous sodium sulfate Dry, filter and concentrate to obtain crude product. Purified by column chromatography (PE:EA=3:1) to give a pale yellow liquid, ie compound 1-(3-cyanopropyl)-1H-imidazole-2-carboxylic acid ethyl ester 19b (260mg, yield 88.1%) .

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; Sichuan University; Li Guobo; Wang Zhenling; (40 pag.)CN111187218; (2020); A;,
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