Month: May 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. 106-65-0, name is Dimethyl succinate, A new synthetic method of this compound is introduced below., Safety of Dimethyl succinate

Potassium (3.10 g, 0.08 mol) andt-BuOH (110 ml) were stirred at 60 C for 3 h under nitrogen until the potassium disappeared. t-BuOH was evaporated under reduced pressure to obtain the white solid (t-BuOK). Then (3,4-dimethoxyphenyl)(phenyl)methanone (5) (15.00 g, 0.06 mol), dimethyl succinate (11.50 g, 0.07 mol), and toluene (100 ml) were added and stirred at 110 C for 34 h. After completion of the reaction, water (100 ml) was added, and the aqueous phase was extracted with toluene (3¡Á50 ml). The combined organic phases were dried over anhydrous Na2SO4, concentrated under reduced pressure, and product 6 was purified by recrystallization from n-hexane-EtOAc, 4:1. Yield 18.86 g (85 %), yellow solid,mp 211-212 C. 1H NMR spectrum, delta, ppm (J, Hz): 3.48(3H, d, J = 2.4, OCH3); 3.59 (2H, s, CH2); 3.78 (3H, s,OCH3); 3.89 (3H, s, OCH3); 6.68-6.73 (2H, m, H Ar); 6.83-6.87 (1H, m, H Ar); 7.10-7.14 (2H, m, H Ar); 7.26-7.29 (3H,m, H Ar). 13C NMR spectrum, delta, ppm: 27.4; 38.4; 51.7;55.9; 81.2; 110.9; 112.5; 122.2; 123.4; 127.9; 128.8; 133.8; 141.9; 148.7; 149.3; 152.8; 169.2; 170.2; 177.2. Found, %:C 67.26; H 5.73. C20H20O6. Calculated, %: C 67.41; H 5.66

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; Zhao, Qian; Yang, Yanhua; Duan, Yingxiang; Tao, Xian; Shen, YingZhong; Chemistry of Heterocyclic Compounds; vol. 54; 9; (2018); p. 840 – 847; Khim. Geterotsikl. Soedin.; vol. 54; 9; (2018); p. 840 – 847,8;,
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Application of 52727-57-8, The chemical industry reduces the impact on the environment during synthesis 52727-57-8, name is Methyl 2-amino-5-bromobenzoate, I believe this compound will play a more active role in future production and life.

Intermediate 108To a solution of methyl 2-amino-5-bromobenzoate (7.38 g, 32.0 mmol) and pyridine (6.3 mL, 81.5 mmol) in 100 mL of anhydrous CH2CL2, was added slowly methane sulfonylchloride (6.5 mL, 79.9 mmol). After stirring overnight, reaction mixture was quenched with 100 mL of IN HC1 (aq). Aqueous mixture was extracted with ethyl acetate (3×120 mL) and combined organic layers were washed 200 mL brine. Organics were dried (MgS04), filtered, and concentrated under reduced pressure to yield intermediate 108 as an off white solid. Silica gel column chromatography (0-30% Ethyl Acetate in Hexanes), yielded intermediate C-C (9.35 g, 95 %) as a white off- white solid.1 H-NMR (CDC13, 300 MHz): delta 10.4 (s, IH), 8.22 (s, IH), 7.63 (s, 2H), 3.96 (s, 3H), 3.05 (s, 3H) LCMS m/z [M+H]+ C9Hi0BrNO4S requires: 307.95. Found 308.06

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 2-amino-5-bromobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (2011); A1;,
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Related Products of 18595-16-9, The chemical industry reduces the impact on the environment during synthesis 18595-16-9, name is Methyl 2-amino-5-methylbenzoate, I believe this compound will play a more active role in future production and life.

EXAMPLE 4 Preparation of 2-phenylthio-6-methyl-4H-3,1-benzoxazin-4-one 2-Amino-5-methylbenzoic acid methyl ester (122 mg, 0.79 mmol) and triethylamine (0.28 ml, 1.96 mmol) were dissolved in THF (10 ml). A 20% solution of phosgene in toluene (0.74 ml, 1.6 mmol) was added, causing immediate formation of a white precipitate.

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 2-amino-5-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Downham, Robert; Palmer, Richard Michael John; Hodson, Harold Francis; Dunk, Christopher Robert; US2003/176429; (2003); A1;,
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Adding a certain compound to certain chemical reactions, such as: 108928-00-3, name is Ethyl 2,4-difluorobenzoate, 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 108928-00-3, category: esters-buliding-blocks

To a solution of 4-chloro-3-(trifluoromethyl)phenol (1.05 g, 5.34 mmol) in DMSO (10 mL) was added potassium carbonate (2.20 g 13.4 mmol, 2.5 eq.) and the suspension was left to stir for 5 minutes after which, ethyl 2,4-difluorobenzoate (1.0 g, 5.34 mmol) was added and the reaction mixture left to stir at 110 C. under nitrogen for 16 hours. The reaction mixture was cooled to room temperature and quenched with 1N NaOH (10 mL) then extracted into ethyl acetate (2¡Á30 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4), filtered and evaporated. The resulting residue was purified by column chromatography (SiO2, 1:1 ethyl acetate: heptane) to give the desired product (mixture of regioisomers) as a colourless oil (1.8 g, 93% yield). This was taken directly on to the next step.LCMS Rt=4.42 minutes

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, Ethyl 2,4-difluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PFIZER LIMITED; US2012/10207; (2012); 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. 61644-18-6, name is Chloromethyl isobutyrate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C5H9ClO2

A 1-L jacketed glass reactor equipped with a nitrogen pad, overhead stirrer motor, down-pumping 45 pitched 4-blade impeller, “h” baffle, West condenser, and thermowell was charged sequentially with solid UK-2A (56.09 g, 0.109 mol, 1.0 equiv), anhydrous Na2C03(23.09 g, 0.218 mol, 2.0 equiv), solid Nal (0.973 g, 0.0065 mol, 6 mol%), nonyl phenyl ketone (1.5269 g, nonreactive internal standard for HPLC analysis), benzo-15-crown- 5 (1.454 g, 0.0054 mol, 5 mol%), neat chloromethyl isobutyrate (16.48 g, 0.120 mol, 1.1 equiv), and ethyl acetate (317 g). The 1-L reactor was placed under an atmosphere of nitrogen, agitation was initiated, and the reaction mixture was heated to 55 C. Samples of the reaction mixture (approximately 1 mL) were removed at 5 h, 10 h, and 24 h. Each sample was added to fresh ethyl acetate (5 mL), syringe filtered, and diluted approximately 6: 1 (v/v) with 0.1% formic acid in N,N-dimethylformamide. The resulting samples were analyzed by HPLC (UV detection, 270 nm) and the molar concentrations of unreacted UK-2A (Formula IV), Formula (VI), and the by-product of Formula (VII) were determined based on the known quantity of internal standard (nonyl phenyl ketone). The conversion of Formula (IV) and the yields of Formula (VI) and Formula (VII) could be calculated on the basis of this information (see for example, Entry 8 of Table 1).

According to the analysis of related databases, 61644-18-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; DOW AGROSCIENCES LLC; JANSMA, Matthew; ADAWAY, Timothy; TRIPPEER, Michael; (19 pag.)WO2017/62362; (2017); A1;,
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Some common heterocyclic compound, 115118-68-8, name is Diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate, molecular formula is C14H24O6, 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: 115118-68-8

Reference Example 3 3-Oxocyclobutane carboxylic acid To diisopropyl 3,3-dimethoxycyclobutane-1,1-dicarboxylate (760 g) obtained from Reference example 2, 20% of hydrochloric acid solution (3.2 L) was added and the mixture was refluxed for four days. After that, the reaction solution was extracted with ethyl acetate, and then the organic layer was dried over magnesium sulfate. Solids were removed, the filtrate was dried under reduced pressure to obtain the title product (700 g). 1H-NMR (CDCl3): 11.2 (1H, s), 3.41 (5H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 115118-68-8, its application will become more common.

Reference:
Patent; Asahi Kasei Pharma Corporation; US2009/298894; (2009); A1;,
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Application of 99548-55-7,Some common heterocyclic compound, 99548-55-7, name is Methyl 4-bromo-2-methylbenzoate, molecular formula is C9H9BrO2, 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.

REFERENCE EXAMPLE 2; Methyl 4-bromo-2-(bromomethyl)benzoate; To a solution of methyl 4-bromo-2-methylbenzoate (9.60 g, 0.42 mol, obtained in reference example 1) in CCI4 (150 mL), Lambda/-bromosuccinimide (7.46g, 0.42mol) and benzoyl peroxide (0.19g, 0.79mmol) were added. The reaction mixture was stirred EPO 4h at room temperature while irradiated with a 250 Watt lamp and it was then filtered to remove the precipitated solids. The filtrate was washed with 1 N NaOH and water and it was dried over Na2SO4. The solvent was evaporated to afford11.87 g of the desired compound as an oil that solidified on standing (yield: 92%, uncorrected).1H NMR (300 MHz, CDCI3) delta (TMS): 3.94 (s, 3 H), 4.90 (s, 2 H)1 7.51 (dd, J = 8.4Hz1 J1 = 2.1 Hz, 1 H), 7.63 (d, J = 1.8 Hz, 1 H), 7.84 (d, J = 8.4 Hz, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 4-bromo-2-methylbenzoate, its application will become more common.

Reference:
Patent; J. URIACH Y COMPANIA S.A.; WO2007/339; (2007); 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. 205448-64-2, name is Methyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-methoxybenzoate, A new synthetic method of this compound is introduced below., SDS of cas: 205448-64-2

45 g (292 mmol) of biphenyl was weighed into a three-necked flask, 150 mL of diphenyl ether was added, the solvent was heated to 180 C under nitrogen atmosphere, and 18 g (53.7 mmol) of compound 4 was rapidly added under a nitrogen atmosphere, and a large amount of gas was released. The temperature was maintained at 170 to 185 C, and the reaction was continued for 45 minutes to stop the heating. Cooled to room temperature, a large amount of yellow solid precipitated, added petroleum ether, filtered, filter cakeThe crude product was washed well with diethyl ether.The crude product was purified by petrol-ethyl acetate (5:2 by volume), suction filtered and dried.A yellow solid (5) of 10.11 g was obtained in a yield of 80.7%.

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; Nanjing Tian Yue Xing Biological Co., Ltd.; Wu Xueping; Chen Yao; (6 pag.)CN109456267; (2019); A;,
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Some common heterocyclic compound, 23426-63-3, name is Methyl 2-bromo-2-methylpropanoate, molecular formula is C5H9BrO2, 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. name: Methyl 2-bromo-2-methylpropanoate

Step B; 2,5-Dimethylhydroquinone 17 (3.73 g, 27 mmol) is dissolved in dimethylformarnide (20 mL) and acetonitrile (60 mL). Powdered cesium carbonate (9.16 g, 28.1 g, 1.04 equiv.) is added to the vigorously stirring solution, followed by 2-bromo-2- methyl-propionic acid methyl ester (3.50 mL, 27.0 mmol, 1 equiv.). The mixture is stirred at 75C for 18 h. Filtration and concentration, followed by purification by silica gel chromatography (5-30% gradient, ethyl acetate in hexanes) yielded 2-(4-hydroxy-2,5- dimethyl-phenoxy)-2-methyl-propionic acid methyl ester 18 as and oil (1.92 g, 8.06 mmol, 30%). The chromatography also yielded recovered hydroquinone 17 (1.20 g, 8.68 mmol, 32%). 18: 1H-NMR (400 MHz, CDCl3) delta = 6.57 (s, IH), 6.50 (s, IH), 4.44 (s, IH), 2.15 (s, 3H), 2.14 (s, 3H), 1.52 (s, 6H). MS calcd. for C13Hi8NaO4 (M+Na+) 261.1, found 261.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 23426-63-3, its application will become more common.

Reference:
Patent; IRM LLC; WO2007/56496; (2007); 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. 24812-89-3, name is Methyl 3-amino-2,4-dimethylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 24812-89-3

To a solution of 6-chloro-3-methyl-pyridine-2-carboxylic acid (0.8 g, 4.6 mmol) in CH2CI2 (4 mL) at room temperature are added methyl 3-amino-2,4- dimethyl-benzoate (0.84 g, 4.6 mmol) and TEA (945.0 mg, 9.3 mmol). After stirring 10 minutes, 1-propanephosphonic acid cyclic anhydride (50% solution in EtOAc, 2.97 g, 9.3 mmol) is added via syringe. After 2 hours at 35 C, the reaction mixture is diluted with saturated NaHC03 solution and extracted with CH2C12. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue is purified by silica gel flash chromatography, eluting with 10% EtOAc in hexanes to give methyl 3-[(6-chloro-3-methyl-pyridine-2-carbonyl)amino]-2,4-dimethyl-benzoate as a colorless oil (1.1 g, 72%). Mass spectrum (m/z): 333.3 (M+H)+.

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 24812-89-3.

Reference:
Patent; ELI LILLY AND COMPANY; BLANCO-PILLADO, Maria-Jesus; MANNINEN, Peter Rudolph; SCHIFFLER, Matthew Allen; VETMAN, Tatiana Natali; WARSHAWSKY, Alan M.; YORK, Jeremy Schulenburg; WO2015/94912; (2015); A1;,
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