Tag: M.W=100-200

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. 10601-80-6, name is Ethyl 3,3-diethoxypropionate, A new synthetic method of this compound is introduced below., Recommanded Product: 10601-80-6

General procedure: A mixture of montmorillonite K-10 (75 mg), an appropriate aniline 1 (150 mg, 1.2 mmol), ethyl-3,3-diethoxypropionate (3) (579 mg, 3 mmol) and an aldehyde (166 mg, 1.34 mmol) in pure water (7.5 mL) was stirred at 90 C for the time mentioned in Table 2. After completion of the reaction (indicated by TLC), the mixture was cooled to room temperature and filtered. The filtrate was extracted with EtOAc (3 × 5 mL). The organic layers were collected, combined, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using ethyl acetate-hexane to give the desired product.

The synthetic route of 10601-80-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Reddy, T. Ram; Reddy, G. Rajeshwar; Reddy, L. Srinivasula; Meda, Chandana Lakshmi T.; Parsa, Kishore V.L.; Kumar, K. Shiva; Lingappa; Pal, Manojit; European Journal of Medicinal Chemistry; vol. 62; (2013); p. 395 – 404;,
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Adding a certain compound to certain chemical reactions, such as: 85953-29-3, name is Methyl 2-chloro-4-fluorobenzoate, 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 85953-29-3, Safety of Methyl 2-chloro-4-fluorobenzoate

A mixture of 2-chloro-4-fluoro-benzoic acid methyl ester (3.51 g, 18.6 mmol), morpholine (1.95 mL, 22.3 mmol) and potassium carbonate (5.12 g, 37.1 mmol) in N-methylpyrrolidinone (20 mL) was stirred at 120C for 5h. The reaction was cooled, diluted with ethyl acetate and filtered through Celite. The filtrate was washed four times with water, once with brine, was dried (sodium sulfate) and evaporated. Purification by flash chromatography (SiO2) eluted with 2:8 ethyl acetate : hexanes to provid 2-chloro-4-morpholin-4-yl-benzoic acid methyl ester (3.08 g, 65% yield) as a white solid. . 1H-NMR (CDCl3, 500 MHz) 7.79 (d, 1H), 6.81 (d, 1H), 6.67 (dd, 1H), 3.81 (s, 3H), 3.78 (m, 4H), 3.20 (m, 4H) ppm; MS (FIA) 256.1 (M+H); HPLC (Method A) 3.275 min.

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

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; WO2004/46120; (2004); A2;,
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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 27741-65-7 as follows. Safety of Ethyl 2-cyclobutylideneacetate

In 40 mL of dry DCM ethyl 2-cyclobutylideneacetate (0.85 g, 6.07 mmol) was allowed to cool to -78 C. under nitrogen atmosphere. To this solution DIBAL-H (1M in toluene) (1.72 g, 12.1 mL, 12.1 mmol) was added dropwise. Reaction was monitored by TLC. When the starting material was consumed completely the reaction mixture was quenched with MeOH/H2O (1:1) (Rf=0.28, 20% ethyl acetate/n-hexane). DCM layer was separated and dried over sodium sulphate. DCM was removed under reduced pressure. Crude product was purified by column chromatography (silica gel 60-120 mesh, 0-20% ethyl acetate and n-hexane as eluent) afforded colorless oil. [0545] Yield: 0.5 g (84%) [0546] 1H NMR (400 MHz, CDCl3): delta 1.61 (br, 1H), 1.91-2.05 (m, 2H), 2.65-2.74 (m, 4H), 4.02 (d, J=7.2 Hz, 2H), 5.30-5.36 (m, 1H).

According to the analysis of related databases, 27741-65-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Cornell University; Coferon, Inc.; Purdue Research Foundation; Barany, Francis; Pingle, Maneesh; Bergstrom, Donald E.; Giardina, Sarah F.; Arnold, Lee Daniel; US2014/194383; (2014); A1;,
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Reference of 56741-34-5, 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. 56741-34-5 name is Methyl 5-amino-2-fluorobenzoate, 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 solution of 5-amino-2-fiuoro-benzoic acid methyl ester (26 g, 153.8 mmol), 3- bromo-benzaldehyde (28.5 g, 153.8 mmol) and -toluenesulfonic acid (590 mg, 3.2 mmol) in toluene (200 mL) was heated to reflux for 12 hours. Then the reaction mixture was cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 5- [(3-bromo-benzylidene)-amino] -2-fiuoro-benzoic acid methyl ester (51.7 g, quant.) as a pale-white solid: MS calcd. for Ci5HiiBrFlN02 337.16, obsd. (ESI+) [(M+H)+] 336.0 & 338.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 5-amino-2-fluorobenzoate, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; CHEN, Li; FENG, Lichun; HUANG, Mengwei; LIU, Yongfu; WU, Guolong; WU, Jim, Zhen; ZHOU, Mingwei; WO2011/128251; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 101-97-3, name is Ethyl 2-phenylacetate, 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 101-97-3, Formula: C10H12O2

(1′-Ethoxycarbonyl-1′-methyl)ethylbenzene To a solution of ethyl phenylacetate (32.8 g, 200 mmol) in THF (1000 mL) under argon was added sodium bistrimethylsilylamide (2M in THF, 100 mL). After 45 minutes. methyl iodide (13 mL) was added over 15 minutes and the mixture was stirred at rt for 30 minutes. Additional sodium bistrimethylsilylamide (2M in THF, 100 mL) was added, followed, after 30 minutes, by methyl iodide (14 mL). After 30 minutes the mixture was diluted with hexane and washed with water. The organic phase was dried, filtered and evaporated to give (1′-ethoxycarbonyl-1′-methyl)ethylbenzene (28.0 g, 146 mmol, 73%).

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; Boehringer Ingelheim Pharmaceuticals, Inc.; US6156784; (2000); A;,
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Some common heterocyclic compound, 22035-53-6, name is Dimethyl isopropylidenemalonate, 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. Computed Properties of C8H12O4

A mixture of 26. 4 grams (0.15 mol) of dimethyl isopropylidenemalonate and 27.5 grams (0.15 mol) of n-bromosuccinimide were stirred in 150 mL carbon tetrachloride containing 1.0 grams benzoyl peroxide. The mixture was refluxed for 16 hours under nitrogen. The reaction was cooled in ice and the succinimide was filtered off and washed with carbon tetrachloride. The solvent was removed under reduced pressure to yield 41.3 grams of impure bromomethyl methyl isopropylidenemalonate as an oil which was used without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22035-53-6, its application will become more common.

Reference:
Patent; EASTMAN KODAK COMPANY; EP608582; (1994); A2;,
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Reference of 5941-55-9, 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 5941-55-9 as follows.

Preparation Example 21 Synthesis of 6-cyano-2-heptylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (intermediate) Eight (8) grams of 2-amino-5-heptylthio-1,3,4-thiadiazole, 5 g of ethyl 3-ethoxy-2-propenoate, 10 g of polyphosphoric acid and 10 ml of xylene were mixed, and the mixture was vigorously agitated at 125C for 30 minutes. After the reaction was finished, the reaction mixture was extracted with water and toluene. The organic layer was washed with a sodium hydrogen carbonate aqueous solution and then with water. The solvent was distilled off and the residue was recrystallized from a n-hexane/ethanol mixture and thus 7.4 g of 2-heptylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. Yield 75%.

According to the analysis of related databases, 5941-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KUMIAI CHEMICAL INDUSTRY CO., LTD.; IHARA CHEMICAL INDUSTRY Co., Ltd.; EP282635; (1989); A3;,
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Electric Literature of 816-27-3, 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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-aminopyridine-4-sulfonamide (112) (500 mg, 2.89 mmol), ethyl 2-ethoxy-2- iminoacetate (629 mg, 4.34 mmol) and DBU (879 mg, 5.78 mmol) in EtOH (10 mL) was heated in a microwave at 135 C for 30 min then allowed to cool to r.t.. The mixture was concentrated and the residue was dissolved in water, acidified to pH 2 with 1 M aqueous HCI and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04, filtered, concentrated and the residue was purified by preparative TLC (MeOH/DCM = 1 :20) to give the product (50 mg, 7% yield) as a yellow solid. LCMS (ES- API): Rt 0.51 min; m/z 255.9 [M+H] +. 1 H NMR (400 MHz, d6-DMSO) delta 13.2 (brs, 1H), 9.09 (s, 1H), 8.81 (d, J = 5.2 Hz, 1H), 7.88 (d, J =5.2 Hz, 1H), 4.42 (t, J = 7.2 Hz, 2H), 1.37 (t, J = 7.2 Hz, 3H).

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

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); 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. 6290-49-9, name is Methyl 2-methoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 2-methoxyacetate

Example 23Hydrogenation of methyl methoxyacetate was carried out according to the following reaction scheme. Methyl methoxyacetate (5.0 mmol), the complex 1a (0.01 mmol), sodium methoxide (0.2 mmol), and methanol (4 mL) were added to a 100 mL autoclave equipped with a stirrer, and the hydrogenation was carried out at 80 C. for 8 hrs with hydrogen pressure of 5 MPa. As a result of the analysis of the reaction for the reaction solution according to gas chromatography, it was found that the reaction conversion rate was 100% and the selectivity was 100%.

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 6290-49-9.

Reference:
Patent; Takasago International Corporation; US2011/237814; (2011); 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. 51122-91-9, name is Dimethyl Isopropylmalonate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 51122-91-9

Step (b): After completion of the step (a), the system was cooled to 65 to 95C, and 28% CH3ONa in methanol (50.1 g) was dropwise added thereto, and then the methanol and toluene were distilled off in the same manner as in the step (a). The heating was stopped when the methanol content of the distillate became 0.01% or below by GC analysis. After the system was cooled to 95 to 105C, (1E)-1,3-dichloro-1-propene (32.1 g) in toluene was added thereto (here, the amount of the toluene was adjusted to be an amount where the mixed ratio of sulfolane and toluene as solvents in the step (b) would be 1/1 (volume ratio), considering the amount removed in the step (a)). Then, the system was heated with stirring for 2 hours, and the production of dimethyl 2-[(2E)-3-chloro-2-propenyl]-2-isopropyl malonate was confirmed by GC analysis. After the system was left to cool to room temperature, the product was added to water (210 g) at 40C or lower. Liquid separation was carried out to remove waste water (285.6 g). The organic layer was washed with a 7% sodium chloride aqueous solution (117.6 g) to remove waste water (128.2 g). Under reduced pressure, concentration was carried out at 70C or lower to obtain 130 g of the desired product in the step (b).

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 51122-91-9.

Reference:
Patent; Asahi Glass Company, Limited; EP1801094; (2007); A1;,
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