Month: February 2021

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. 46193-76-4, name is Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, A new synthetic method of this compound is introduced below., Quality Control of Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

Ethyl-6-nitro-4H-thieno[3,2-b]pyrrole-5-carboxyIate (95). Pulverized Cu(NO3)2′ hydrate (953 mg, 4.10 mmol) dissolved in acetic anhydride (8.2 niL) was added dropwise to a solution of carboxylate 96 dissolved in acetic anhydride (10 mL) at 0 0C. The addition was completed in 1.5 h and the mixture was then stirred at r.t. for 2 h. After filtration the organic layer was poured over ice and extracted with diethyl ether (3×30 mL). The combined organic layers were washed with saturated aqueous sodium carbonate solution and dried over MgSO4. After the removal of organic solvent, the residue was purified by column chromatography (EtOAc/Hexane: 1/6) to give the desired nitration product 94 (148 mg, 12 %) as a light yellow solid along with another nitration product 95 (300 mg, 25%).

The synthetic route of 46193-76-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNITED STATES OF AMERICA, AS REPRESENTED BY THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES; THOMAS, Craig J.; AULD, Douglas S.; INGLESE, James; SKOUMBOURDIS, Amanda P.; JIANG, Jian-Kang; BOXER, Matthew; WO2010/42867; (2010); A2;,
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Application of 403-33-8, A common heterocyclic compound, 403-33-8, name is Methyl 4-fluorobenzoate, molecular formula is C8H7FO2, 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: 4-fluorobenzoic acid as the raw material, methanol as a reaction solvent, a small amount of concentrated sulfuric acid catalyst, followed by stirring under heating at reflux, thin layer chromatography (TLC) to track progress of the reaction, a certain amount after the completion of the reaction NaHCO3Solution for hydrazine and the reaction liquid solution to give ester intermediate (3-1), continue to add more than the corresponding proportion of hydrazine hydrate reaction mixture was heated with stirring at reflux, thin layer chromatography (TLC) to track progress of the reaction, the reaction after completion of the reaction solution was added to a certain amount of water, then a large amount of white sink to the bottom, suction filtration to afford intermediate hydrazides (3-2)

The synthetic route of 403-33-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan People Hospital; Shi Jianyou; (21 pag.)CN106957242; (2017); A;,
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Synthetic Route of 3377-20-6,Some common heterocyclic compound, 3377-20-6, name is Diethyl 2-methylenemalonate, molecular formula is C8H12O4, 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.

nBuLi solution (2.5 M in hexanes, 2.5 mL, 6.2 mmol) was added, dropwise over 3 min., to a cooled (dry ice/EtOH/ethylene glycol bath at .20 C) solution of N,N,N?-trimethylethylenediamine (0.90 mL,6.9 mmol) in 2-MeTHF (15 mL). After stirring for 20 min., 2- chlorobenzaldehyde (0.70 mL, 6.2 mmol) was added dropwise, maintaining the internal reaction temperature below .20 C. After 10 min., more nBuLi solution (2.5 M in hexanes, 7.6 mL, 19 mmol) was added dropwise, again maintaining the internal reaction temperature below .20 C. After stirring at this temperature for 2.5 h, the reaction mixture was cooled in a dry ice/acetone bath. Diethyl ketomalonate (4.1 mL, 27 mmol) was added to the reaction mixture dropwise, maintaining the internal reaction temperature below .50 C. After 5 min., the reaction was quenched by rapid addition of aq. HCl (1.0 M, excess), and cooling was ended. The resulting mixture was extracted with dichloromethane (2x), and the combined organic layers were dried (sodium sulfate) and evaporated to afford a clear, orange oil. Repeated chromatographic purification (48 g silica gel, 1:19 to 1:1 EtOAc/heptane gradient; then 48 g silica gel, 1:9 to 2:3 EtOAc/heptane gradient; and finally 54 g silica gel, 1:9 dichloromethane/heptane to dichloromethane to 1:19 EtOAc/dichloromethane gradient) afforded the title compound as a clear, colorless oil (224 mg, 11 % yield). GCMS (EI) m/z: 314 [M+] (6.2 %). 1H NMR (400 MHz, CDCl3) ? 1.28 (t, J = 7.1 Hz, 3H), 1.31 (t, J = 7.1 Hz, 3H), 2.92 (s, 1H), 4.23 (dq, J = 10.8, 7.1 Hz, 1H), 4.30 (dq, J = 10.8, 7.1 Hz, 1H), 4.32 (dq, J = 10.7, 7.1 Hz, 1H), 4.36 (dq, J = 10.7, 7.1 Hz, 1H), 6.00 (s, 1H), 6.90 (d, J = 8.2 Hz, 1H), 6.96 (d, J = 7.9 Hz, 1H), 7.22 (t, J = 8.1 Hz, 1H).

The synthetic route of 3377-20-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Rocke, Benjamin N.; Conn, Edward L.; Eisenbeis, Shane A.; Ruggeri, Roger B.; Tetrahedron Letters; vol. 53; 41; (2012); p. 5467 – 5470;,
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Synthetic Route of 681465-85-0, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 681465-85-0 name is Methyl 4-amino-3-isopropoxybenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

4-(2-(Benzyloxy)-3-isopropoxy-4-nitrobenzamido)-3-isopropoxybenzoate 2-Benzyloxy-3-isopropoxy-4-nitrobenzoic acid (51.5 mg, 0.16 mmol) was dissolved in CH2Cl2 (8 mL) and preactivated with Ghosez’s reagent (66.0 muL, 0.50 mmol) for 3 hours at 40 C. 3-Isopropoxy-4-aminomethylbenzoate (0.12 g, 0.55 mmol) was dissolved in CH2Cl2 (8 mL) and N,N-diisopropylethylamine (DIPEA) was added (0.20 mL, 1.12 mmol). The solution containing the acid chloride was then added and the reaction mixture stirred for 2 days at 40 C. The solvent was then removed and the crude product was purified by preparative HPLC (RP-18; run time 100 min; H2O/MeCN=100:0?0:100; tr=80 min) providing the title compound (56.9 mg, 0.11 mmol, 68%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) delta 10.33 (s, 1H-NH), 8.55 (d, J=8.5 Hz, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.70 (dd, J=8.5, 1.7 Hz, 1H), 7.59 (d, J=8.7 Hz, 1H), 7.57 (d, J=1.7 Hz, 1H), 7.25-7.12 (m, 5H), 5.25 (s, 2H), 4.75-4.67 (m, 1H), 4.67-4.59 (m, 1H), 3.93 (s, 3H), 1.40 (d, J=6.2 Hz, 6H), 1.28 (d, J=6.0 Hz, 6H) ppm. 13C NMR (100 MHz, CDCl3) delta 167.0, 161.4, 151.1, 147.9, 146.1, 145.2, 134.1, 132.9, 132.9, 130.0, 129.4, 128.7, 125.79, 125.6, 123.3,120.1, 119.5, 113.3, 78.9, 77.4, 71.7, 52.3, 22.6, 22.1 ppm. HRMS (ESI): Calculated for C28H31N2O8 (M+H+: 523.2080. found: 523.2075.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-amino-3-isopropoxybenzoate, and friends who are interested can also refer to it.

Reference:
Patent; HELMHOLTZ-ZENTRUM FUeR INFEKTIONSFORSCHUNG GMBH; GOTTFRIED WILHELM LEIBNIZ UNIVERSITAeT HANNOVER; Baumann, Sascha; Herrmann, Jennifer; Mohr, Kathrin; Steinmetz, Heinrich; Gerth, Klaus; Raju, Ritesh; Mueller, Rolf; Hartmann, Rolf; Hamed, Mostafa; Elgaher, Walid A.M.; Moreno, Maria; Gille, Franziska; Wang, Liang Liang; Kirschning, Andreas; (196 pag.)US2016/145304; (2016); A1;,
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Electric Literature of 4630-80-2, 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. 4630-80-2, name is Methyl cyclopentanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of sodium hydride (1.87 g, 55% in mineral oil, 42.9 mmol) in THF (10 ml) was added a solution of methyl cyclopentanecarboxylate (5 g, 39.0 mmol) and acetonitrile (1.92 g, 2.45 ml, 46.8 mmol) in THF (3 ml) dropwise at 70C. The mixture was heated to 70C overnight, then cooled to room temperature, diluted with IN HCl and extracted with EtOAc. The combined organic layers were washed with water and brine, dried with Na2S04 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 95:5 – 85: 15) to afford the title compound (4105 mg, 77%) as light yellow liquid.

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

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CECCARELLI, Simona M.; CONTE, Aurelia; KUEHNE, Holger; KUHN, Bernd; NEIDHART, Werner; OBST SANDER, Ulrike; RUDOLPH, Markus; WO2013/64465; (2013); 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. 107947-17-1, name is Methyl 3-bromo-4-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of Methyl 3-bromo-4-chlorobenzoate

The compound methyl 4-chloro-3-bromobenzoate 19b (1.2 g, 4.8 mmol), trimethyl Silyl acetylene (0.95 g, 9.7 mmol), palladium acetate (108 mg, 0.48 mmol), triphenylphosphine (254 mg, 0.97 mmol), cuprous iodide (185 mg, 0.97 mmol) and triethylamine (25 mL) Mix in a tube and heat and stir at 100 C for 15 hours.After the reaction was completed, the solution was desolvated under reduced pressure, and the residue was purified by column chromatography silica gel chromatography (petroleum ether / ethyl acetate = 10/1) to obtain the target product 4-chloro-3-((trimethylsilyl) ethynyl). Methyl benzoate 19c (1 g, yellow solid), yield: 78%.

The synthetic route of 107947-17-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); A;,
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Reference of 61367-07-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 61367-07-5 name is Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A mixture of 1.5 g (7.745 mmol) of methyl frans-4-aminocyclabexanecarboxyiate hydrochloride, 4 mL (46.5 mmol) of 2-fiuoropyridine and 1.35 mL (7.75 mmol) of DIPEA was stirred at 125 C in a pressure-resistant glass reactor for 20 hours, then cooled to room temperature. The reaction mixture was diluted with 20 mL of ethyl acetate, washed with 2×30 mL of water and saturated NaCI solution, the organic phase was dried over anhydrous Na2S04, filtered and concentrated to yield 325 mg (18%) of the title compound. MS (ESI) m/z 235.1 (M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl trans-4-aminocyclohexanecarboxylate hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; RICHTER GEDEON NYRT.; BATA, Imre; SZELECZKY, Zsolt; SZONDINE KORDAS, Krisztina; SZANTO, Gabor; (191 pag.)WO2019/116325; (2019); 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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, A new synthetic method of this compound is introduced below., Recommanded Product: 3618-04-0

(1) Synthesis of ethyl 4-((tert-butyl(diphenyl)silyl)oxy)cyclohexanecarboxylate To a solution of 25 g of 4-hydroxycyclohexanecarboxylic acid in 125 ml of N,N-dimethylformamide were sequentially added 21.7 g of imidazole and 39.6 ml of tert-butyl (diphenyl)silyl chloride under cooling with ice, followed by stirring the reaction mixture at room temperature for 3 hours. To the reaction mixture was added water and extracted with hexane. The resulting hexane solution was washed with brine, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound.

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; Iwasawa, Yoshikuzu; Kato, Tetsuya; Kawanishi, Nobuhiko; Masutani, Kouta; Mita, Takashi; Nonoshita, Katsumasa; Ohkubo, Mitsuru; US2008/58347; (2008); A1;,
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Synthetic Route of 18358-63-9, 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. 18358-63-9, name is Methyl 4-(methylamino)benzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

4.13 Lithium 4-[methyl(phenylsulfonyl)amino1benzoate; To a mixture of methyl 4-(methylamino)benzoate (1 mmol), 4-dimethylaminopyridine (2 mg), and diisopropylethylamine (1.1 mmol) in acetonitrile (3 ml) was added benzenesulfonyl chloride (1.1 mmol). The reaction mixture was stirred for 16h, and the mixture concentrated by nitrogen stream. The crude product was partitioned between 1 M HCI (aq) and ethyl acetate. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with 1 M HCI (aq), water, brine and dried over sodium sulfate. The solvent was removed and the crude product was purified by flash column chromatography on silica to give methyl 4- [methyl(phenylsulfonyl)amino]benzoate as a white solid (249 mg, 81 %).

The synthetic route of Methyl 4-(methylamino)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIVIR AB; WO2007/144379; (2007); 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. 37466-90-3, name is Ethyl 3,4-diaminobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 3,4-diaminobenzoate

General procedure: A mixture of o-phenylenediamine (1.0 mmol), aryl aldehyde(1.0 mmol) and chromium(III) salen complex nanoparticles supported on AlPO4(2.0 mol%) in ethanol (5 mL) was stirred at room temperature. After completion of the reaction (TLC), the mixture was centrifuged and rinsed with ethanol (3 ¡Á 15 mL). The recovered nanocatalyst was dried and stored for another consecutive runs. The solvent was evaporated to give the crude product, which was purified by silica gel column chromatography employing n-hexane/ethyl acetate (8:1) as eluent.

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 37466-90-3.

Reference:
Article; Sharghi, Hashem; Aberi, Mahdi; Doroodmand, Mohammad Mahdi; Shiri, Pezhman; Journal of the Iranian Chemical Society; vol. 14; 7; (2017); p. 1557 – 1573;,
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