Month: July 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. 26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

To a solution of 2-amino-4,5-dimethoxy-benzoic acid methyl ester 1 (422 mg, 2 mmol) and 3- methylene-cyclobutanecarbonitrile (558 mg, 6 mmol) in 1,4-dioxane (3 mL) was added 4N HC1 in 1,4- dioxane (8 mL). The mixture was stirred at 100 °C overnight. The resulting mixture was cooled to room temperature and poured into chilly NaHC03 solution (20 mL) to give a precipitate. The solid was collected by filtration, washed with water (30 mL) and dried to give a mixture of compound (156) and (157) (440 mg, yield: 72percent). MS: m/z 307.1 (M-H+).

The synthetic route of 26759-46-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SANFORD-BURNHAM MEDICAL RESEARCH INSTITUTE; DUKE UNIVERSITY; PINKERTON, Anthony; MALONEY, Patrick; HERSHBERGER, Paul; PEDDIBHOTLA, Satyamaheshwar; HEDRICK, Michael; BARAK, Lawrence; CARON, Marc; WO2014/100501; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 35120-18-4, name is Ethyl 1-bromocyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 1-bromocyclobutanecarboxylate

Cyclobut-1-enecarboxylic acid2,3 Cyclobut-1-enecarboxylic acid was prepared according to the procedure for preparation of 3,3-dimethylcylobutene carboxylic acid as described by Campbell et al. with minor modifications. KOH (6.00 g, 107 mmol) and toluene (90 ml) were mixed and then heated to reflux until the KOH dissolved. Ethyl 1-bromocyclobutanecarboxylate (4.90 g, 23.7 mmol) was added dropwise without heating. The reaction mixture was heated at reflux for 1 h, then cooled to RT. Cold water (60 ml) was added, the aqueous layer was washed with pentane (2*40 ml) and the pH was adjusted to 2.5 with 30% aq H2SO4. The product was then extracted from the aqueous layer with Et2O (4*40 ml) and dried over anhydrous Na2SO4. The Et2O was evaporated to give a yellow oil. The oil was dissolved in pentane (50 ml) and the upper layer was separated from the lower layer. The upper layer was cooled in an acetone-dry ice bath and stirred for 20 min. The resulting precipitate was filtered and dried under vacuum (1.14 g, 49% yield). The dried solid was stored at -20 C. to prevent decomposition. 1H-NMR (400 MHz, CDCl3) delta 10.23 (bs, 1H), 6.94 (t, J=1.2 Hz, 1H), 2.76 (t, J=3.2 Hz, 2H), 2.51 (td, J=3.2 Hz, 1.2 Hz, 2H); 13C-NMR (100 MHz, CDCl3) delta 167.5, 150.1, 138.4, 29.1, 27.5.

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 35120-18-4.

Reference:
Patent; The Research Foundation of State University of New York; US2011/212046; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 2318-25-4, 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. 2318-25-4 name is Ethyl 3-ethoxy-3-iminopropionate 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.

Procedure AA .5000 mL, 4-neck flask was fitted with a stirrer, thermometer, condenser, and gas inlet/outlet. The equipped flask was charged with 265.7 g (1.12 mol. 1.0 eq) of 5-(4-methyl- piperazin-l-yl)-2-nitroaniline and 2125 mL of 200 proof EtOH. The resulting solution was purged with N2 for 15 minutes. Next, 20.0 g of 5percent Pd/C (50percent H2O w/w) was added. The reaction was vigorously stirred at 40-500C (internal temperature) while H2 was bubbled through the mixture. The reaction was monitored hourly for the disappearance of 5-(4- methyl-piperazin-l-yl)-2-nitroaniline by HPLC. The typical reaction time was 6 hours.After all the 5-(4-methyl-piperazin-l-yl)-2-nitroaniline had disappeared from the reaction, the solution was purged with N2 for 15 minutes. Next, 440.0 g (2.25 mol) of ethyl 3-ethoxy-3-iminopropanoate hydrochloride was added as a solid. The reaction was stirred at 40-500C (internal temperature) until the reaction was complete. The reaction was monitored by following the disappearance of the diamino compound by HPLC. The typical reaction time was 1-2 hours. After the reaction was complete, it was cooled to room temperature and filtered through a pad of Celite filtering material. The Celite filtering material was washed with absolute EtOH (2 x 250 mL), and the filtrate was concentrated under reduced pressure EPO providing a thick brown/orange oil. The resulting oil was taken up in 850 niL of a 0.37percent HCl solution. Solid NaOH (25 g) was then added in one portion, and a precipitate formed. The resulting mixture was stirred for 1 hour and then filtered. The solid was washed with H2O (2 x 400 mL) and dried at 500C in a vacuum oven providing 251.7 g (74.1percent) of [6-(4- methyl-piperazin-l-yl)-lH-benzoimidazol-2-yl]-acetic acid ethyl ester as a pale yellow powder.Procedure BA 5000 mL, 4-neck jacketed flask was fitted with a mechanical stirrer, condenser, temperature probe, gas inlet, and oil bubbler. The equipped flask was charged with 30O g (1.27 mol) of 5-(4-methyl-piperazin-l-yl)-2-nitroaniline and 2400 mL of 200 proof EtOH (the reaction may be and has been conducted with 95percent ethanol and it is not necessary to use 200 proof ethanol for this reaction). The resulting solution was stirred and purged with N2 for 15 minutes. Next, 22.7 g of 5percent Pd/C (50percent H2O w/w) was added to the reaction flask. The reaction vessel was purged with N2 for 15 minutes. After purging with N2, the reaction vessel was purged with H2 by maintaining a slow, but constant flow of H2 through the flask. The reaction was stirred at 45-55°C (internal temperature) while H2 was bubbled through the mixture until the 5-(4-methyl-piperazin-l-yl)-2-nitroaniline was completely consumed as determined by HPLC. The typical reaction time was 6 hours. After all the 5-(4-methyl-piperazin-l-yl)-2-nitroaniline had disappeared from the reaction, the solution was purged with N2 for 15 minutes. The diamine intermediate is air sensitive so care was taken to avoid exposure to air. 500 g (2.56 mol) of ethyl 3-ethoxy-3- iminopropanoate hydrochloride was added to the reaction mixture over a period of about 30 minutes. The reaction was stirred at 45-55°C (internal temperature) under N2 until the diamine was completely consumed as determined by HPLC. The typical reaction time was about 2 hours. After the reaction was complete, the reaction was filtered while warm through a pad of Celite. The reaction flask and Celite were then washed with 200 proof EtOH (3 x 285 mL). The filtrates were combined in a 5000 mL flask, and about 3300 mL of ethanol was removed under vacuum producing an orange oil. Water (530 mL) and then IM HCL (350 mL) were added to the resulting oil, and the resulting mixture was stirred. The resulting solution was vigorously stirred while 30percent NaOH (200 mL) was added over a period of about 20 minutes maintaining the internal temperature at about 25-300C while the pH was brought to between 9 and 10. The resulting suspension was stirred for about 4 hours while maintaining the internal temperature at about 20-250C. The resulting mixture was filtered, EPO and the filter cake was washed with H2O (3 x 300 mL). The collected solid was dried to a constant weight at 500C under vacuum in a vacuum oven providing 345.9 g (90.1percent) of [6-(4- methyl-piperazin-l-yl)-lH-benzoimidazol-2-yl]-acetic acid ethyl ester as a pale yellow powder. In an alternative work up procedure, the filtrates were combined and the ethanol was removed under vacuum until at least about 90percent had been removed. Water at a neutral pH was then added to the resulting oil, and the solution was cooled to about O0C. An aqueous 20percent NaOH solution was then added slowly with rapid stirring to bring the pH up to 9.2 (read with pH meter). The resulting mixture was then filtered and dried as described above. The alternative work up procedure provided the light tan to light yellow product in yields as high as 97percent.

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

Reference:
Patent; NOVARTIS AG; WO2006/127926; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 23680-40-2,Some common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, molecular formula is C4H3BrO2, 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.

5-Deuterio-2-(n-pentyl)furan (1-d1) (0.6 mmol), methyl 3-bromopropiolate 2 (0.5 mmol), and toluene (1.5 mL) were added to a two-necked flask, and the mixture was stirred at reflux for 24 h under nitrogen atmosphere. After completion of the initial Diels-Alder reaction, silica gel (150 mg) was added under a flow of nitrogen and the reaction mixture was stirred at reflux for 2 h. After removal of the solvent and filtration through a pad of silica, 1H NMR spectra of products were measured.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-bromopropiolate, its application will become more common.

Reference:
Article; Sonoda, Motohiro; Ikeda, Ayu; Shinohara, Hiroyuki; Hayagane, Naoya; Ogawa, Akiya; Tanimori, Shinji; Research on Chemical Intermediates; vol. 45; 1; (2019); p. 13 – 21;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 213598-10-8, name is Methyl 3-bromo-4-isopropoxybenzoate, belongs to esters-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 213598-10-8, Recommanded Product: 213598-10-8

Step C: Methyl 3-cyano-4-isopropyloxybenzoate; A mixture of 1.32 g (4.83 mmol) of methyl 3-bromo-4-isopropyloxybenzoate (from Step B), 341 mg (2.90 mmol) of zinc cyanide, 67 mg (0.12 mmol) of 1, 1′- bis (diphenylphosphino) ferrocene, 44 mg (0.05 mmol) of tris (dibenzylideneacetone) dipalladium (0)-chloroform complex and 50 L ofH20 in 5.0 mL of DMF was stirred at 120 C for 48 h. The mixture was cooled, then partitioned between EtOAc and sat’d NaCl. The aqueous layer was separated and extracted with 3 x EtOAc. The organic layers were combined, dried over MgS04 and concentrated. Chomatography on a Biotage 40M cartridge using 9: 1 v/v hexanes/EtOAc gave 802 mg of the title compound : 1H NMR (500 MHz, CDC13) 8 1.44 (d, J = 6.2, 6H), 3.91 (s, 3H), 4. 71-4. 79 (m, 1H), 6.99 (d, J = 8.9, 1H), 8.18 (dd, J = 2.2, 8.8, 1H), 8.24 (d, J=2. 1, 1H).

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

Reference:
Patent; MERCK & CO., INC.; WO2005/58848; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

14064-10-9, name is Diethyl 2-chloromalonate, belongs to esters-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. Computed Properties of C7H11ClO4

[00788] (i) Production of ethyl 4-hydroxy-2-(2-methylpyrazolo[l,5-a]pyridin-3-yl)-l,3-thiazole-5- carboxylate and ethyl 4-ethoxy-2-(2-methylpyrazolo[l,5-a]pyridin-3-yl)-l,3-thiazole-5-carboxylate [00789] A suspension of 2-methylpyrazolo[l,5-a]pyridine-3-carbothioamide hydrochloride (1.7 g, 7.5 mmol) produced in Example 11-B (v) and diethyl chloromalonate (2.0 g, 11 mmol) in 2-propanol (25 mL) was stirred at 900C for 4 hr with heating. The reaction mixture was cooled to room temperature, and MPI09-013Pl RNWOM PCT FILING the precipitated solid was collected by filtration and dried to give ethyl 4-hydroxy-2-(2- methylpyrazolo[1.5-a]pyridin-3-yl)-l,3-thiazole-5-carboxylate (1.45 g, 64percent) as a yellow solid.[00790] 1H-NMR (DMSO-d6, 300 MHz) delta 1.27 (3H, t, J = 7.1 Hz), 2.65 (3H, s), 4.23 (2H, q, J = 7.1Hz), 7.12 (IH, dt, J = 1.3, 6.8 Hz), 7.51 – 7.65 (IH, m), 8.36 (IH, d, J = 8.9 Hz), 8.79 (IH, d, J = 6.8 Hz),11.76 (IH, s).00791] Saturated aqueous sodium bicarbonate solution (100 mL) and ethyl acetate (100 mL) were added to the filtrate, and the mixture was stirred for 30 min. The organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to give ethyl 4-ethoxy-2-(2- methylpyrazolo[l,5-a]pyridin-3-yl)-l,3-thiazole-5-carboxylate (200 mg, 32percent) as a yellow solid.[00792] 1H-NMR (DMSO-d6, 300 MHz) delta 1.27 (3H, t, J = 7.1 Hz), 1.42 (3H, t, J = 6.9 Hz), 2.65 (3H, s), 4.23 (2H, q, J = 7.1 Hz), 4.61 (2H, q, J = 6.9 Hz), 7.12 (IH, dt, J = 1.3, 6.9 Hz), 7.55 – 7.69 (IH, m),8.32 (IH, d, J = 8.9 Hz), 8.79 (IH, d, J = 6.9 Hz).

The synthetic route of 14064-10-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; TAKEDA PHARMACEUTICAL COMPANY LIMITED; BANNO, Hiroshi; HIROSE, Masaaki; KURASAWA, Osamu; LANGSTON, Steven, P.; MIZUTANI, Hirotake; SHI, Zhan; VISIERS, Irache; VOS, Tricia, J.; VYSKOCIL, Stepan; WO2010/90716; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 17100-63-9, name is Methyl 4-bromo-3-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C9H9BrO3

methyl 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (0285) To a solution of methyl 4-bromo-3-methoxybenzoate (7.3 g, 29.79 mmol) in dioxane (150 mL) was added 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (8.3 g, 32.69 mmol), Pd(dppf)Cl2.CH2Cl2 (2.4 g, 2.94 mmol) and potassium acetate (8.76 g, 89.26 mmol) at room temperature. The reaction mixture was stirred for 16 h at 80 C., cooled to room temperature, and treated with water (100 mL). The resulting solution was extracted with ethyl acetate (250 mL×3). The organic phases were combined, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by flash chromatography eluting with ethyl acetate in hexane (0% to 10% gradient) to yield methyl 3-methoxy-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate as yellow oil (6.0 g, 69%). MS: m/z=293.0 [M+H]+.

According to the analysis of related databases, 17100-63-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 2439-35-2, name is 2-(Dimethylamino)ethyl acrylate, 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. Application In Synthesis of 2-(Dimethylamino)ethyl acrylate

ExamplesThe foregoing may be better understood by reference to the following example, which is presented for purposes of illustration and is not intended to limit the scope of the invention.A pilot plant unit was assembled to demonstrate the process and to obtain comparative data. Using the process equipment described above, the process was repeatedly executed in successive experiments. Each experiment used a specific set of conditions and was run for a period of time long enough to reach steady-state conditions. In addition to sampling the final product, an in-process sample was also taken from the lower portion of the CSTR by means of a dip-tube installed in the CSTR, in order to observe the physical state of the reaction mixture in the lower portion of the reactor at any given time.The final product was analyzed for the impurities acrylic acid (AA), N,N-dimethylaminoethyl acrylate (DMAEA), and N,N-dimethylaminoethanol (DMAE). The level of acrylic acid impurity in the final product is commonly measured to give an indication of the level of acrylate ester hydrolysis over the course of the entire process. Also measured were the total amine impurities (DMAEA+DMAE), which indicate the total level of TAS present in the final product. These amine impurities are primarily generated in the CSTR or reaction section of the process, where they arise from hydrolytic side reactions that ultimately form DMAEA and DMAE salts that are unreactive towards the desired quaternization reaction. We have discovered that the amount of these total amines (DMAEA and DMAE) is an important indicator of the quality of the final product, as these amine impurities cause the final product to be unstable towards polymerization during processing and storage.As shown in table 1, control runs 1 and 4 gave unacceptably high levels of residual acrylic acid and unquaternized amine impurities. In contrast, run 11 provided extremely low levels of unquaternized amine impurities in the final product, while also providing low levels of acrylic acid impurity. Runs 9 and 10B, provided reasonably low levels of acrylic acid and unquaternized amine impurities in the final product, but the impurity levels were higher than those provided by run 11.

The synthetic route of 2-(Dimethylamino)ethyl acrylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fair, Barbara E.; Reed, Peter E.; Vers, Leonard M. Ver; Brammer, JR., Larry E.; Holada, Charles J.; Huang, Cheng-Sung; Sawant, Kailas B.; US2011/178327; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, belongs to esters-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 3618-04-0, SDS of cas: 3618-04-0

Chloro(1 ,1-dimethylethyl)dimethylsilane (1 15 g; 0.76 mol) was added in portions over 1 hour to a solution of commercially available ethyl 4-hydroxycyclohexanecarboxylate (118 g; 0.68 mol), imidazole (103 g; 1.52 mol) and dimethylformamide (400 ml.) stirred under an atmosphere of argon. A small exotherm was observed resulting in the reaction mixture temperature increasing to -40 0C. The mixture was stirred at room temperature overnight then poured into 10% citric acid solution (2 L) and extracted with diethyl ether (2 x 800 ml_). The ether extracts were washed with water, brine and then dried (Na2SC>4) and the solvent was removed to give the title compound as an oil (198.4 g) 1H NMR delta (CDCI3, 400 MHz): 0.01 (6H, m), 0.85 (9H, s), 1.2 (3H, m), 1.3-1.5 (2H, m), 1.6 (2H, m), 1.85-2 (3H, m), 2.15-2.3 (1 H, m) 3.5 (0.4H, m) 3.86 (1 H, m) 4.1 (1 H, m).

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; GLAXO GROUP LIMITED; WO2009/37294; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 88709-17-5, name is Ethyl 2-ethoxy-4-methylbenzoate, belongs to esters-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 88709-17-5, HPLC of Formula: C12H16O3

To the suspension of 700 ml of cyclo hexane, 86 g (1.0 mol) of N-bromo succinimide and 3 g (0.03 mol) of AIBN was added 100 g (1.0 ml) of Ethyl-2-ethoxy-4-methyl benzoate. Heated the resulted mass to reflux and stirred for 3-5 hr. Cooled to 50-60 C. and charged 200 ml of water, then stirred for 10-15 min. Separated the aqueous phase and organic phase. The organic phase was washed with 200 ml of 5% hydrose followed by water (200 ml) at 50-60 C. Total organic phase was distilled completely under vacuum at below 60 C. Cooled to 25-35 C. and the title compound was isolated from residue with 100 ml n-Heptane at 0-5 C. The obtained compound was recrystallised from 400 ml of n-Heptane. Dried the compound under reduced pressure at 45-50 C. The yield of the recrystallised compound is 59.2 g (43%). [0038] The obtained product was characterised by analytical techniques like IR, Mass and 1H-NMR

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 2-ethoxy-4-methylbenzoate, and friends who are interested can also refer to it.

Reference:
Patent; DR. REDDY’S LABORATORIES LIMITED; DR. REDDY’S LABORATORIES, INC; US2004/249188; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics