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. 369-26-6, name is Methyl 3-amino-4-fluorobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 3-amino-4-fluorobenzoate

Into a 100-mL round-bottom flask, was placed methyl 3-amino-4-fluorobenzoate (1 g, 5.91 mmol), HCl (6 M, 10 mL). This was followed by the addition of a solution of NaNO2 (630 mg, 9.13 mmol) in water (2 mL) dropwise with stirring at 0oC. The resulting solution was stirred for 20 min at 0oC. The above mixture was added to a saturated solution of SO2 in AcOH (20 mL) and CuCl2 (800 mg, 5.95 mmol) dropwise with stirring at 0oC. The resulting solution was stirred for 1 h at RT. The reaction was then quenched by the addition of 20 mL of water. The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined and dried over anhydrous Na2SO4, then concentrated under vacuum. This resulted in 1.5 g (crude) of the title compound as a yellow oil. The crude product was used in the next step.

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; IFM THERAPEUTICS, INC; GLICK, Gary; GHOSH, Shomir; ROUSH, William R.; (185 pag.)WO2017/184623; (2017); A1;,
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14062-29-4, name is Ethyl 2-(3-chlorophenyl)acetate, 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. SDS of cas: 14062-29-4

m-Chlorotoluene (1.89 g), ethanol (46 mg), di-tert-butyl peroxide (73 mg, 1 equivalent), and Pd(Xantphos)Cl2 (3.8 mg, 1 mol %) were added into a reaction kettle, into which 10 atm carbon monoxide was introduced. The reaction was heated to 120 C., and stirred at this constant temperature for 16 h. After the reaction was completed, carbon monoxide was discharged, and 82 mg ethyl m-chlorophenylacetate was obtained by column chromatography, in a yield of 83%. 1HNMR (400 MHz, CDCl3) delta 1.24 (t, J=7.2 Hz, 3H), 3.58 (s, 2H), 4.13 (q, J=7.2 Hz, 2H), 7.15-7.18 (m, 1H), 7.24-7.26 (m, 1H), 7.29 (s, 1H); 13CNMR (100 MHz, CDCl3) delta 14.2, 40.9, 61.1, 127.3, 127.5, 129.5, 129.8, 134.3, 135.9, 170.9; HRMS (ESI) calcd. for C10H11ClNaO2 [M+Na]: 221.0340. found: 221.0342. The ethyl m-chlorophenylacetate obtained was dissolved in 1,4-dioxane. 6 N sodium hydroxide solution was added, and the reaction was heated to 60 C. After 2 h of reaction, the pH value was adjusted to 1 by adding 2 N hydrochloric acid. After removing the organic solvent under reduced pressure, 64 mg product m-chlorophenylacetic acid was obtained by extraction with ethyl acetate, and the yield of hydrolysis was 91%.

The synthetic route of 14062-29-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences; Huang, Hanmin; Xia, Chungu; Xie, Pan; US2013/303798; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 685-88-1, name is Diethyl fluoromalonate, 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 685-88-1, Formula: C7H11FO4

General Procedure: In a small vial, MBH carbonate 1a-e (0.25 mmol, 1 equiv), 2-fluoromalonate 2, (67 mg, 0.375 mmol, 1.5 equiv), and catalyst I (8 mg, 0.025 mmol, 10 mol %) in 1 mL of toluene were stirred at room temperature overnight. The crude mixture was monitored by 1H NMR and after completion the crude was purified by column chromatography, affording compound 3. 1,1-diethyl 3-methyl 1-fluoro-2-phenylbut-3-ene-1,1,3-tricarboxylate (3a):1H NMR (400 MHz, CDCl3) delta 7.31-7.28(m, 2H), 7.24-7.20(m, 2H), 6.37-6.37(m, 1H), 6.17(m, 1H), 5.08 (d, JH-F = 35.2 Hz, 1H), 4.24-4.22 (m, 2H), 4.03-4.02(m, 2H), 3.63(s, 3H), 1.24-1.22(t, J = 7.1 Hz, 3H), 1.03-1.02(t, J = 7.1 Hz, 3H). 13C NMR (100 MHz, CDCl3) delta 166.2, 165.2, 164.9, 164.8, 164.5, 138.1, 138.1, 134.9, 129.8, 129.8, 128.2, 127.8, 127.02, 126.9, 98.0, 95.9, 62.9, 62.7, 52.2, 49.0, 48.8, 13.8, 13.7; 19F NMR (376 MHz, CDCl3) delta -174.1 (d, J = 35.4 Hz). HRMS (ESI) calcd. for C18H25FNO6 (M+NH4)+, 370.1666 found 370.1665. Enantiomeric excess: 81%, -65.6 (CHCl3; c = 0.8 g/100 mL) determined by HPLC (Daicel Chiralpak IA, i-PrOH/Hexane = 5/95), UV 254 nm, flow rate 0.8 mL/min, major 9.7 min, minor 10.9 min.

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:
Article; Wang, Bing; Companyo, Xavier; Li, Jing; Moyano, Albert; Rios, Ramon; Tetrahedron Letters; vol. 53; 32; (2012); p. 4124 – 4129;,
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Synthetic Route of 7335-27-5,Some common heterocyclic compound, 7335-27-5, name is Ethyl 4-chlorobenzoate, molecular formula is C9H9ClO2, 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: A mixture of substituted ethyl benzoate 2 (10 mmol) and hydrazinehydrate (20 mmol) in ethanol was stirred at room temperaturefor 3 h and then filtered. The crude product recrystallizedfrom absolute alcohol to give 3a-l, which were used directly forthe next step. Under this same condition, the intermediate compounds 8a-d were also prepared.

The synthetic route of 7335-27-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; He, Haifeng; Wang, Wei; Zhou, Yuan; Xia, Qin; Ren, Yanliang; Feng, Jiangtao; Peng, Hao; He, Hongwu; Feng, Lingling; Bioorganic and Medicinal Chemistry; vol. 24; 8; (2016); p. 1879 – 1888;,
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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. 13195-64-7, name is Diisopropyl malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Diisopropyl malonate

(1) 200 mmol of diisopropyl malonate was reacted with 440 mmol of propargyl bromide plus 830 mmol of sodium hydride as a catalystInto 210mL anhydrous acetonitrile in ice water bath, stirring reaction for 8 hours, the product was washed with water, extracted with ethyl acetate, dried under reduced pressure to give the product as a brown solid, namely compound 1.

The synthetic route of 13195-64-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Anhui Normal University; Hu Yimin; Fang Bo; (16 pag.)CN106946707; (2017); 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. 84228-44-4, name is Methyl 4-amino-3-chlorobenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 84228-44-4

A mixture of methyl 4-amino-3-chlorobenzoate (1.0 g, 5.4 mmol), n-pentyl nitrite (0.95 g, 8.1 mmol) and iodine (1.78 g, 7.0 mmol) was stirred under refluxing for 1 h. The mixture was diluted with methylene chloride (30 ml). The purple solution was washed with saturated sodium thiosulfate solution, brine, and dried over sodium sulfate. The title compound was obtained after flash column using EtOAc:hexane/2:98 as the eluant.

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; MERCK & CO., INC.; WO2007/79186; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 135908-33-7, name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, 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. Safety of Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate

General method D, 4-(isopropoxycarbonylamino)bicyclo[2.2.2]octane-1-carboxylate.

The synthetic route of Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cyteir Therapeutics, Inc.; Castro, Alfredo C.; McComas, Casey Cameron; Vacca, Joseph; Maclay, Tyler; (132 pag.)US2019/77799; (2019); A1;,
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Related Products of 50893-36-2,Some common heterocyclic compound, 50893-36-2, name is 1-Chloroethyl ethyl carbonate, molecular formula is C5H9ClO3, 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.

Preparation of 1-bromoethyl ethyl carbonate The reaction is carried out as in Example 5 starting with 1-chloroethyl ethyl carbonate in the presence of various catalysts and replacing the trimethylsilane bromide with acetyl bromide. The quantities of free agents employed and the results obtained are given in the table below.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Chloroethyl ethyl carbonate, its application will become more common.

Reference:
Patent; Societe Nationale des Poudres et Explosifs; US5202454; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 1559-02-0, 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. 1559-02-0 name is Diethyl 1,1-cyclopropanedicarboxylate, 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.

To 500 ml of a three-necked flask was added 200 ml of methanol and 30 g of 1,1-cyclopropanedicarboxylic acid diethyl ester, cooled to 10 C, stir A solution of sodium hydroxide (NaOH 6.4 g, water 32 ml) was added dropwise, The reaction was carried out at room temperature for 3 hours, the reaction was terminated, the solvent was distilled off under reduced pressure, A white solid. To the solid was added 200 ml of water and 150 ml of ethyl acetate, ] Stir and layer, discard the organic phase. The aqueous layer was adjusted to pH 3 to 4 with 2 mol / L hydrochloric acid, Ethyl acetate extraction (200 ml x 2), The organic phase was dried over anhydrous sodium sulfate, filtered, The solvent was distilled off under reduced pressure, To give a colorless translucent oil

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Diethyl 1,1-cyclopropanedicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhao Rui; Li Xinlu; Meng Qingyi; Zhang Xiquan; Shi Xiangfei; (25 pag.)CN103965104; (2017); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference 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.

General procedure: Methyl 3-bromopropiolate 2 (0.5 mmol), furan 1 (0.6 mmol) and distilled toluene (1.5 mL) were added in atwo-necked flask, and the mixture was stirred at reflux for 24 h under nitrogen atmosphere. After completion ofthe initial DielsAlder reaction, FeCl3 (10 mol%) was added under 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, a product 4 was purified by silica gel column chromatography or PTLC using a mixture of ethyl acetate and n-hexane as an eluent.

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; Shinohara, Hiroyuki; Sonoda, Motohiro; Hayagane, Naoya; Kita, Shota; Tanimori, Shinji; Ogawa, Akiya; Tetrahedron Letters; vol. 55; 38; (2014); p. 5302 – 5305;,
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Ester – an overview | ScienceDirect Topics