Category: 924-99-2

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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C7H13NO2

a) Ethyl 2-[(2,5-difluorophenyl)carbonyl]-3-(dimethylamino)-2-propenoateA solution of 2,5-difluorobenzoyl chloride (5.26 g, 29.8 mmol) in toluene (100 mL) was treated with ethyl-3-(dimethylamino)-2-propenoate (5.27 g, 36.8 mmol), followed by triethylamine (5.9 mL, 42.5 mmol). The mixture was stirred at 9O0C for 6.5 h then allowed to cool, and the precipitate removed by filtration. The filtrate was concentrated under reduced pressure to give a residue which was purified by flash chromatography (silica gel,50-100% diethyl ether in petroleum ether [b.p. 40-600C]) to give the title compound as a yellow oil (0.95 g); ESMS m/z 284.4 [M+H]+.

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; PLIVA-ISTRAZIVACKI INSTITUT D.O.O.; WO2006/50942; (2006); A1;,
Ester – Wikipedia,
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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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, A new synthetic method of this compound is introduced below., Safety of Ethyl 3-(dimethylamino)acrylate

General procedure: All microwave reactions were carried out in a capped (10 mL) microwave-vessel (Borosilicate glass vial sealed) that was placed in a microwave cavity. The pressure was set at 17 bar (average of an effective pressure = 4 bar) with power 75 W. DIEA (3.4 g, 3.4 mmol) was added to a solution of either 2,5-difluoro-4-(pyrrolidin-1-yl) benzoylchloride 12 (0.83 g, 3.4 mmol) or 2,5-difluoro-4-(pyrrolidin-1-yl)benzothioyl chloride 13 (0.88 g, 3.4 mmol) and ethyl-3-(diethylamino)acrylate 14 (0.45 g, 3.1 mmol) in acetonitrile (5 mL). The mixture reaction was held at 100 C for 20 min. After the reaction vessel was cooled to room temperature, the crude product was diluted with water (10 mL) and extracted with ethyl acetate(3 × 10 mL). The organic layers were combined, dried over Na2SO4, filtered, evaporated and purified by a flash column chromatography (eluent n-hexane: acetone, 3:1)to give the titled compounds. Ethyl-2-(2,5-difluoro-4-(pyrrolidin-1-yl)benzoyl)-3-(dimethylamino) acrylate (15)Yellow oil (Rf = 0.3), Yield 85%. IR (KBr) numax in cm-1:2993 (C-H, Ar), 2953 (C-H), 1760 (C=O), 1692 (C=O),1654 (C=C, Ar), 1592 (C-N). 1H NMR (400 MHz, DMSOd6):delta = 7.77 (1H, s, CH), 7.32 (1H, d, J = 5.0 Hz, CH-Ar),6.88 (1H, d, J = 5.2 Hz, CH-Ar), 4.2 (2H, q, J = 7.1 Hz,CH2), 3.47-3.42 (4H, m, 2CH2), 3.1 (6H, s, 2CH3), 2.01-1.97 (4H, m, 2CH2), 1.32 (3H, t, J = 4.2 Hz, CH3).

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Almashal, Faeza A.; Alshawi, Jasim M.; Dhumad, Adil M.; Jassem, Ahmed M.; Medicinal Chemistry Research; (2020);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 924-99-2,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.

General procedure: The substituted benzoyl chloride (18.1 mmol), 3-(N,N-dimethylamino)acrylic acid ethyl ester (18.1 mmol), triethylamine (27.1 mmol) was dissolved in 30 mL of toluene, stirred at 90 C for 4 h, concentrated and column chromatographed to give Intermediate 1. ethyl 2-(2,4-difluorobenzoyl)-3-(dimethylamino)acrylate (R2=H): yield 65%

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; Chen, Fen Er; He, Qiuqin; Mao, Tianqi; Wan, Zhengyong; (17 pag.)CN103965163; (2016); B;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 924-99-2,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.

The compound 2,4-difluorobenzoic acid (950 mg, 6 mmol) was dissolved in 2 ml of thionyl chloride,Heated to 80 C reflux2 hours,After completion of the reaction, the solvent was dried to give an oily compound,The oily compound was placed on an oil pump for half an hour,Immediately put the next step.The compound of the previous step was quickly dissolved in dry toluene,And ethyl 3- (dimethylamino) acrylate (1 g, 7 mmol) was added,Triethylamine (1.01 g, 10 mmol)Heated to 90 C,Fully stirred for 12h,Cooled to room temperature, spin dry solvent, dissolved in ethyl acetate and washed several times with water,After concentration, the compound 1a (1.42 g, 85%) was obtained as a yellow oil by column chromatography elution (petroleum ether: ethyl acetate = 10: 1 to 2: 1).

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

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Long Yaqiu; Geng Meiyu; Li Bowen; Ai Jing; Xu Zhongliang; (65 pag.)CN107151240; (2017); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, 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 924-99-2, Product Details of 924-99-2

[1311] to a solution of ethyl 3-(dimethylamino)acrylate (165 mg, 1.2 mmol) and tea (233 mg, 2.3 mmol) in THF (15 ml) was added a solution of compound 277b (400 mg, 2.3 mmol) in THF (5 ml) drop-wise over 30 mins. The mixture was stirred at 20 C for 12 hours. The reaction mixture was concentrated under reduced pressure to give a residue. The residue was purified by preparatory-tlc (SiO2, petroleum ether: ethyl acetate = 1: 1) to give compound 277c (240 mg, yield: 44.4%) as a pale yellow oil. 1H NMR (400mhz, CDCl3) delta 8.94 (s, 1h), 7.51 – 7.36 (m, 2h), 7.21 – 7.14 (m, 1h), 7.13- 7.04 (m, 1h), 4.17 (q, 7 = 7.1 hz, 2h), 1.15 (t, 7 = 7.2 hz, 3h).

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; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; ADLER, Marc; EMAYAN, Kumaraswamy; MA, Jingyuang; (687 pag.)WO2018/64119; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 924-99-2,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.

A solution of ethyl 3-(dimethylamino)acrylate (4.33 mL, 30.3 mmol) and triethylamine (2.446 mL, 17.55 mmol) in Et2O (46 mL) was added dropwise to a solution of (Z)-2-chloro-N-hydroxybenzimidoyl chloride (2.3 g, 12.10 mmol) in Et2O (46.0 mL) to give a white suspension which was stirred overnight at 20 C. After 19 h, the salts were filtered and then rinsed with Et2O (30 mL). The filtrate was concentrated to dryness to give 5.86 g of an orange liquid which was purified by flash chromatography using a mixture of hexane/Et2O to afford ethyl 3-(2-chlorophenyl)isoxazole-4-carboxylate 3a (2.36 g, 77% yield) as a colorless oil; 1H NMR (DMSO-d6) was consistent with the desired product; MS m/z 252.1 (MH+); HPLC 100%, Rt=1.96 min, column 2.

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

Reference:
Patent; Lamarre, Daniel; US2015/133495; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 924-99-2, A common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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: Ethyl 4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tertahydropyrimidine-5-carboxylate 6a (Table 2, entry 1). To a mixture of thiourea 12a (23.0 mg, 0.302 mmol), 4-chlorobenzaldehyde 13a (63.0 mg, 0.448 mmol), and ethyl 3-dimethylaminoacrylate 9 (64.0 mg, 0.447 mmol) in anhydrous DMF (0.3 mL) was added anhydrous aluminum chloride (8.0 mg, 0.0600 mmol) at room temperature, and the reaction mixture was stirred at 110 C for 3 h. To the mixture was added EtOAc (10 mL) and 1 M HCl aqueous solution (5 mL), and the organic layer was separated. The aqueous layer was extracted with EtOAc (10 mL), and the combined organic layers were washed with water (5 mL) and brine (5 mL), dried over anhydrous MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane-EtOAc (4:1 to 2:1)] to give 6a (78.9 mg, 0.266 mmol, 88%) as pale yellow crystals.

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Arai, Rie; Cho, Hidetsura; Gokurakuji, Yuki; Kikuchi, Hidetomo; Kubo, Takanori; Nakamura, Yuri; Nishimura, Yoshio; Sunaga, Katsuyoshi; Yuan, Bo; Tetrahedron Letters; (2020);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, 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 924-99-2, name: Ethyl 3-(dimethylamino)acrylate

95 mg (0.27 mmol) of 2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoic acid were boiled with 0.98 ml of thionyl chloride under reflux for 3 hours. The thionyl chloride was distilled off, and the residue was mixed with 3 ml of toluene and concentrated in vacuo. The residue was taken up in 2 ml of toluene and added to a solution of 39 mg (0.27 mmol) of ethyl 3-dimethylaminoacrylate, 6 mul of triethylamine and 1 ml of toluene. The mixture was heated at 90 C. for 3 hours. The mixture was concentrated and chromatographed on silica gel (heptane:ethyl acetate=75:25 to 0:100 in 45 minutes). 30 mg (23%) of the desired product were obtained. MS: M+H=477/479

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

Reference:
Patent; Aventis Pharma Deutschland GmbH; US2005/182085; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, A new synthetic method of this compound is introduced below., Formula: C7H13NO2

This compound was prepared by refluxing a mixture of 2,4-dichloro-5-fluoro-3-nitrobenzoic acid (I), (10.2 g, 40 mmol), and thionyl chloride (SOCl2) (19.0 g, 160 mmol), dissolved in dry benzene (120 ml) at 75-80 C for 3-4 h under anhydrous conditions. The mixture was then distilled off under reduced pressure to remove solvent and excess thionyl chloride. Dry benzene was then added twice (2 x 20 ml) into the reaction vessel and the mixture was re-distilled so as to remove traces of thionyl chloride. The resulting 2,4-dichloro-5-fluoro-3-nitrobenzoyl chloride (II), formed as thick oil, was used as such for the next step without further purification. To a stirred and cooled (5-10 C) solution of ethyl 3-(N,N-dimethylamino)acrylate (6.3 g, 44 mmol) and triethylamine (4 ml, 8.1 g, 80 mmol) in dry benzene (50 ml), a solution of the crude acid chloride (prepared above) in dry benzene (25 ml) was added drop by drop. The resulting mixture was stirred continuously for 2 h at room temperature under anhydrous conditions. Then, the solution was refluxed at 90 C for 90 minutes. This crude product was evaporated to dryness, redissolved in chloroform; the chloroform was extracted with water (30 ml) and dried (with anhydrous MgSO4). The solvent, chloroform, was then evaporated to dryness under reduced pressure. The residual product (about 20 ml) was soaked in methanol (10 ml) whereby the title compound III was obtained as a yellowish powder that was collected by suction filtration and dried, mp = 140-141 C (decomposition), yield 13.8 g (91 %), Rf value in system (1) = 0.89 and in system (2) = 0.850. 1H NMR(500 MHz, CDCl3): delta 0.95 (t, J= 7.1 Hz, 3H, OCH2CH3), 2.97 (s, 3H) and 3.37 (s, 3H) [N (CH3)2], 3.94 (q, J= 7.1 Hz, 2H, OCH2Me), 7.27 (d,3JH-F= 8.2 Hz, 1H, H-6?), 7.91 (br s, 1H, N-C(3)-H). 13C NMR (75 MHz, CDCl3): delta 13.8 (CH3CH2), 43.3, 48.4 [N (CH3)2], 60.2 (CH2Me), 100.9 (C-2), 114.5 (d,2JC-F= 23.3 Hz, C-4?), 116.9 (d, 2JC-F= 23.1 Hz, C-6?), 118.2 (d, 3JC-F= 4.5 Hz, C-1?), 144.2 (d, 3JC-F= 6 Hz, C-3?), 148.8 (br d, 4JC-F= 1.3 Hz, C-2?), 156.6 (d, 1JC-F= 254 Hz, C-5?), 160.5 (N-C-3), 166.5 (CO2Et), 185.1 (C = O). HRMS ((+ve)-ESI): m/z calculated for C14H14Cl2FN2O5[M+H]+: 379.02638, found: 379.02591. Calculated for C14H13Cl2FN2O5(379.17): C, 44.35; H, 3.46; N, 7.39. Found: C, 44.30; H, 3.38; N, 7.62.

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:
Article; Alabsi, Yousef; Al-Hiari, Yusuf; Kasabri, Violet; Arabiyat, Shereen; Bashiti, Rabab; Alalawi, Sundos; Al-Shahrabi, Rula; Revue Roumaine de Chimie; vol. 63; 12; (2018); p. 1123 – 1134;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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 924-99-2 as follows. Safety of Ethyl 3-(dimethylamino)acrylate

Example 194-Methyl-2- [2-(3-pyridin-2-yl-isoxazol-4-yl)-ethyl] -thiazole-5-carboxylic acid (tetra- hydro-pyran-4-yl)-amidea) 3-Pyridin-2-yl-isoxazole-4-carboxylic acid ethyl esterTo a solution of N-chlorosuccinimide (54.7 g, 409 mmol) in DMF (1 L) was added pyridine-2-carbaldoxime (50 g, 409 mmol) portionwise and the resulting mixture was then stirred for 64 h at room temperature. To this solution was then added ethyl 3-(N5N- dimethylamino)acrylate (58.6 g, 409 mmol) and triethylamine (82.9 mL, 819 mmol) in chloroform (10 mL) and the resulting mixture was then stirred for 14 h at room temperature and poured onto a mixture of ice water and HCl (4 N, 100 mL) and extracted with ethylacetate. The organic extract was then washed with water, saturated aqueous sodium hydrogen carbonate solution, brine, dried with sodium sulfate, filtered and evaporated. Purification by distillation afforded the title product (58.9 g, 66%) which was obtained as a light brown liquid. Bp 125-127C at 0.4 mbar. MS: m/e = 219.2 [M+H]+.

According to the analysis of related databases, 924-99-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; JAKOB-ROETNE, Roland; LUCAS, Matthew, C.; THOMAS, Andrew; WO2010/127974; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics