Tag: M.W=100-200

Synthetic Route of 103-26-4, 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. 103-26-4, name is Methyl cinnamate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1,8-Diazabicyclo[5.4.0]undec-7-ene (0.28 ml, 1.85 mmol, 3.0 eq) wasadded to a solution of (E)-3-Phenyl-acrylic acid methyl ester (100 mg, 0.62mmol, 1.0 eq) in methanol (0.35 mL). The resulting solution was stirred at roomtemperature and hydroxylamine in aqueous solution 50% (0.38 ml, 6.17 mmol, 10.0eq) was added. After 30 minutes the reaction was stopped and purified bypreparative HPLC to afford (E)-N-Hydroxy-3-phenyl-acrylamide(92 mg, 0.56 mmol, 91%) as an off-whitesolid: MS ES+ m/z 164.35(M+H)+; 1H NMR (400 MHz, DMSO-d6) delta 10.67 (s, 1H), 7.56 (d, J = 7.2 Hz, 2H), 7.48(d, J = 15.8 Hz, 1H), 7.44 – 7.30 (m, 3H), 6.51 (d, J = 15.8 Hz,1H) ; 13C NMR (101 MHz, DMSO-d6) delta 163.0, 138.6, 135.0, 129.7, 129.1, 127.7, 119.

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 cinnamate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Beillard, Audrey; Bhurruth-Alcor, Yushma; Bouix-Peter, Claire; Bouquet, Karinne; Chambon, Sandrine; Clary, Laurence; Harris, Craig S.; Millois, Corinne; Mouis, Gregoire; Ouvry, Gilles; Pierre, Romain; Reitz, Arnaud; Tomas, Loic; Tetrahedron Letters; vol. 57; 20; (2016); p. 2165 – 2170;,
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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. 4341-76-8, name is Ethyl 2-butynoate, A new synthetic method of this compound is introduced below., category: esters-buliding-blocks

Step A: (Z)-methyl pent-2-enoate To a mixture of ethyl but-2-ynoate (50 g, 446 mmol) and Lindlar catalyst (9.49 g, 4.46 mmol) in 1 L round-bottom flask THF (1013 mL) and pyridine (101 mL) were added. The reaction mixture was degassed and purged with nitrogen (5*). The reaction was then blanked with a hydrogen balloon. After about 48 h the suspension was filtered through a pad of Celite washing with THF (3*100 mL). The THF was removed in vacuo at about 40 C. and 200 mbar. The residue was diluted with Et2O (1 L) and washed with water (3*200 mL) followed by 20% CuSO4 aqueous solution (5*200 mL) followed by water (3*150 mL) and dried over MgSO4, filtered and the solvent was removed in vacuo at about 40 C. and 200 mbar to give (Z)-methyl pent-2-enoate (45.3 g, 89%) as an oil. 1H NMR (400 MHz, CDCl3) delta 6.34-6.30 (m, 1H), 5.82-5.75 (m, 1H), 4.20-4.14 (m, 2H), 2.14 (dd, 3H), 1.31-1.27 (m, 3H).

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; ABBVIE INC.; Wishart, Neil; Bonafoux, Dominique F.; Frank, Kristine E.; Hobson, Adrian D.; Konopacki, Donald B.; Martinez, Gloria Y.; Wang, Lu; US2013/72470; (2013); A1;,
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Electric Literature of 13831-03-3, A common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, 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.

To a suspension of copper(I) iodide (335 mg) in tetrahydrofuran (100 mL) was added t-butyl prpiolate (3.63 mL), diisopropylethylamine (4.62 mL) and a solution of 5(R)-azidomethyl-3-[4-(1-cyanocyclopropan-1-yl)phenyl]oxazolidin-2-one (5.00 g) in tetrahydrofuran (10 mL), the mixture was stirred at room temperature for 2.5 hours, and then concentrated in vacuo. After dilution of the residue with ethyl acetate, the resulting precipitates were filtered off, and then concentrated in vacuo. Treatment of the residue with ethyl acetate gave t-butyl 1-[5(R)-3-[4-(1-cyanocyclopropan-1-yl)phenyl]-2-oxooxazolidin-5-ylmethyl]-1,2,3-triazole-4-carboxylate (6.85 g). [0423] MS (EI+) m/z: 409 (M+). [0424] HRMS (EI+) for C21H23N5O4 (M+): calcd, 409.1750; found, 409.1729.

The synthetic route of 13831-03-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fukuda, Yasumichi; US2003/225107; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 121-98-2, name is Methyl 4-methoxybenzoate, 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 121-98-2, Formula: C9H10O3

Methyl-4-methoxybenzoate (i) was refluxed with 5 mL of hydrazine hydrate solution in 15 mL of methanol for 6 h. The excess hydrazine and methanol was then removed in vacuo to obtain crude product which was then recrystallized from methanol to afford pure 4-methoxybenzohydrazide in 92% yield. Pure 4-methoxybenzohydrazide(20 mmol, 3.32 g) were refluxed with Lawesson’s reagent (20 mmol,8.09 g) of in dry toluene for 8 h to get corresponding 4-methoxybenzothiohydrazide. The crude product was washed with diethyl ether and crystallized from methanol to get pure 4-methoxybenzothiohydrazide in 91% yield. In order to get thiadiazole derivatives 1-25, a mixture of 4-methoxybenzothiohydrazide (0.5 mmol) and the corresponding aromatic aldehyde (0.5 mmol) were taken together in around-bottomed flask and was then added drop wise POCl3 (5 mL) carefully. The reaction mixture was heated to reflux for 4-6 h, then cooled to room temperature and poured onto crushed ice. NaHCO3 solution was added and the resulting solid mass precipitated out was filtered, dried, and crystallized from methanol in good to excellent yields.

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

Reference:
Article; Taha, Muhammad; Barak Almandil, Noor; Rashid, Umer; Ali, Muhammad; Ibrahim, Mohamed; Gollapalli, Mohammed; Mosaddik, Ashik; Mohammed Khan, Khalid; Bioorganic Chemistry; vol. 91; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 34846-90-7, name is Methyl 3-methoxyacrylate, 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 34846-90-7, Safety of Methyl 3-methoxyacrylate

6-Hydrazino-N,N-dimethyl-pyrimidin-4-amine (0.40 g, 2.61 mmol) and methyl-3-methoxyprop-2-enoate (606 mg, 5.22 mmol) in MeOH (4 ml_) was heated to 130¡ãC in the microwave for 1 h. Further methyl-3-methoxyprop-2-enoate (303 mg, 2.61 mmol) was added and reaction was heated at 130¡ãC for a further 1 h. The reaction mixture was evaporated and purified by column chromatography eluting with DCM/NH3 2 M in MeOH (100:0 to 95:5). The recovered starting hydrazine, the uncyclised intermediate and methyl -3-methoxyprop-2-enoate (1.0 ml_) in MeOH (5.0 ml_) were heated in a microwave at 130¡ãC for 2 h. The crude was evaporated to dryness and purified by column chromatography eluting with DCM/NH3 2 M in MeOH (100:0 to 97:3). The product from both columns was slurried in MeOH (2.0 ml_) and filtered to give after drying the title compound as a white solid (62 mg, 11percent). LCMS (QC Acidic method): Rt = 2.59 min; [MH]+ = 206.0; >99.5percent purity 1H NMR (400 MHz; DMSO-cfe, d): 12.8 (1H, bs), 8.4 (1H, d), 7.6 (1H, bs), 7.0 (1H, bs), 5.5 (1H, bs) and 3.1 (6H, s)

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; CADO BIOTECHNOLOGY IVS; CRUMPLER, Simon Ross; DALBY-BROWN, William; PALLIN, Thomas David; HANSEN, John Bondo; WINTHER, Anne-Marie Lund; (240 pag.)WO2019/141957; (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. 185629-32-7, name is Methyl 4-amino-3-fluorobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 4-amino-3-fluorobenzoate

j00495J To a solution of methyl 4.-ainino-3-fluorohenzoate (500 mg, 3 mrnol) and DIPEA (1.65 mL, 9 mmol) in MeCN (5 mL) was added acryloyl chloride (320 mg, 16 mmoi) dropwise at 0 C. The reaction was stirred at ii for I h, then Na2CO3 aq.(sat,) was added, the resulting mixture was extracted with DCM (20 rnL x 2). The combined organic layer was concentrated and recrvstalized from EA to give YLIUi)1 164 (190 mg, 28 %) as white solid, LCMS (mz): 224 [M + H]+.

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; DANA-FARBER CANCER INSTITUTE, INC.; HAO, Mingfeng; GRAY, Nathanael, S.; ZHANG, Tinghu; KWIATKOWSKI, Nicholas, P.; (307 pag.)WO2017/44858; (2017); 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 15224-11-0 as follows. category: esters-buliding-blocks

Step 2: Ethyl 2-((methylsulfonyloxy)methyl)cyclopropanecarboxylate (C-6) To a solution of alcohol C-5 (0.50 g, 3.47 mmol) and triethylamine (1.45 mL, 10.41 mmol) in anhydrous methylene chloride (12.0 mL) at 0 C. was added methanesulfonic anhydride (0.908 g, 5.21 mmol) in one portion. The reaction mixture was then stirred at room temperature for 1 h, diluted with diethyl ether (50 mL) and quenched with an aqueous pH 7 phosphate buffer solution (30 mL). The aqueous layer was extracted with diethyl ether (2*50 mL). The combined organic extracts were then successively washed with an aqueous pH 7 phosphate buffer solution (70 mL) and brine (70 mL), dried over MgSO4, filtered, and concentrated to give ethyl 2-((methylsulfonyloxy)methyl)cyclopropanecarboxylate (C-6) as a colorless oil (0.698 g, 91% yield). This material was immediately placed under argon and dissolved with anhydrous DMF (1.57 mL) to give a 2.0 M stock solution, which was used as such for the next step.

According to the analysis of related databases, 15224-11-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ting, Pauline C.; Aslanian, Robert; Caplen, Mary Ann; Cao, Jianhua; Chan, Tin-Yau; Kim, David; Kim, Hyunjin; Kim, Jae-Hun; Kuang, Rongze; Lee, Joe F.; Schwerdt, John; Wu, Heping; Zorn, Nicolas; US2011/224137; (2011); A1;,
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Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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. Recommanded Product: 924-99-2

b) Ethyl 3-dimethylamino-2-(2-fluoro-4acetoxybenzoyl)-2-propenoateA stirred solution of Intermediate 25a (4.91 g) in DCM (80 mL) at 200C was treated with oxalyl chloride (3.25 mL) and DMF (2 drops). After 2 h the clear solution was evaporated and re-evaporated from DCM (2x). The acid chloride was re-dissolved in toluene (100 mL) and treated with triethylamine (5.17 mL) and ethyl 3-dimethylaminopropenoate (4.13 g). After stirring for 2 h at 900C the mixture was filtered and the solution flash chromatographed (silica gel 40 to 100% EtOAc in petroleum ether [b.p. 40-600C]) to give the title compound as a yellow gum (4.3 g); APCI m/z 324.0 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 924-99-2, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/50940; (2006); A1;,
Ester – Wikipedia,
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Application of 27492-84-8, 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 27492-84-8 as follows.

General procedure: To a suspension of 5,6,6a,7,8,9-hexahydro-4H-phenalene-2-carboxylic acid (0.338 g, 1.56 mmol) in benzene (7.5 ml) was added SOCl2 (2.5 ml). The reaction mixture was refluxed for 4 h, then evaporated, and the residue was dissolved in benzene (3 ml) and pyridine (10 ml). Methyl 4-aminobenzoate (0.259 g, 1.71 mmol) and 4-DMAP (0.020 g, 0.164 mmol) were added to the resulting solution. The reaction mixture was stirred at rt for 15 h, then poured into 2 M aqueous HCl and extracted with AcOEt. The organic phase was washed with 10percent aqueous Na2CO3. Usual work-up gave a residue, which was purified by silica gel column chromatography(AcOEt/n-hexane = 1:10) to afford methyl 4-[(5,6,6a,7,8,9-hexahydro-4H-2-phenalenyl)carboxamido]benzoate (0.478 g,88percent). To a suspension of the above ester (0.385 g, 1.10 mmol) in EtOH (10 ml) was added 2 M aqueous NaOH (7.5 ml). The reaction mixture was stirred at 60 ¡ãC for 1 h, then cooled, acidified by adding 2 M aqueous HCl and extracted with CHCl3. Usual work-up gave a residue, which was purified by recrystallization from EtOH to afford 7a (0.348 g, 94percent).

According to the analysis of related databases, 27492-84-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Amano, Yohei; Noguchi, Masayuki; Nakagomi, Madoka; Muratake, Hideaki; Fukasawa, Hiroshi; Shudo, Koichi; Bioorganic and Medicinal Chemistry; vol. 21; 14; (2013); p. 4342 – 4350;,
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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. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H13NO2

PREPARATION 44 To a mixture of ethyl 4-aminocinnamate (300 mg), triethylamine (167 mg) and dichloromethane (3 ml) was added a solution of propionyl chloride (182 mg) in dichloromethane (1 ml) in an ice-water bath, and the mixture was stirred for 1 hour at the same temperature. To the reaction mixture was added 4 drops of N,N-dimethylpropanediamine, and the mixture was further stirred for 5 minutes. The reaction mixture was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was crystallized from diisopropyl ether to give ethyl 4-propionamidocinnamate (341 mg) as a colorless powder. mp: 138¡ã C. NMR (CDCl3, delta): 1.26 (3H, t, J=8 Hz), 1.34 (3H, t, J=8 Hz), 2.42 (2H, q, J=8 Hz), 4.26 (2H, q, J=8 Hz), 6.37 (1H, d, J=16 Hz), 7.21 (1H, br s), 7.49 (2H, d, J=8 Hz), 7.58 (2H, d, J=8 Hz), 7.68 (1H, d, J=16 Hz)

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; Fujisawa Pharmaceutical Co., Ltd; US5574042; (1996); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics