Tag: M.W=100-200

Electric Literature of 144851-82-1,Some common heterocyclic compound, 144851-82-1, name is Methyl 2-amino-3-fluorobenzoate, molecular formula is C8H8FNO2, 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 suspension of methyl triphenylphosphonium bromide (2.4 eq) and sodium amide (3.2 eq) in toluene (0.1 M) was stirred at RT for 3 h. After cooling down to 00C, a solution of Dl in toluene (0.1 M) was added to the suspension and the reaction mixture was heated to 500C for 3 h. 30 min. Then, The precipitate was filtered off and the solvent was evaporated under reduced pressure giving a crude that was purified by flash chromatography on silicagel, using AcOEt/PE (7:3) as solvent, affording the title compound as a yellow powder.1U NMR (500 MHz, CDCl3) delta: 7.78-7.68 (m, 6H), 7.62-7.54 (m, 3H), 7.52-7.45 (m, 7H), 6.97-6.89 (m, IH), 6.56-6.48 (m, IH), 5.76 (bs, 2H), 4.32-4.20 (m, IH). MS (ES) C26H2iFNOP requires: 413, found: 414 (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 Methyl 2-amino-3-fluorobenzoate, its application will become more common.

Reference:
Patent; ISTITUTO DI RICERCHE DI BIOLOGIA MOLECOLARE P. ANGELETTI S.P.A.; WO2009/27730; (2009); A1;,
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Electric Literature of 27741-65-7, These common heterocyclic compound, 27741-65-7, name is Ethyl 2-cyclobutylideneacetate, 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.

In 1:1:0.5 THF/water/Methanol (10:10:5 mL each), ethyl 2-cyclobutylideneacetate (1.2 g, 8.57 mmol) and lithium hydroxide monohydrate (2.15 g, 51.4 mmol) was added at room temperature. Reaction mixture was allowed to stir at room temperature for 16 h. TLC showed absence of starting material (Rf=0.4, 30% ethyl acetate/n-hexane). THF and Methanol was removed under reduced pressure. Aqueous layer was acidified with citric acid and extracted with ethyl acetate. Crude product was purified by column chromatography (silica gel 60-120 mesh ethyl acetate/n-hexane as eluent) to afford white solid. [0505] Yield: 0.6 g (62%) [0506] 1H NMR (400 MHz, CDCl3): delta 2.02-2.20 (m, 2H). 2.86 (t, J=7.8 Hz, 2H), 3.14 (t, J=7.8 Hz, 2H), 5.59 (t, J=2 Hz, 1H).

Statistics shows that Ethyl 2-cyclobutylideneacetate is playing an increasingly important role. we look forward to future research findings about 27741-65-7.

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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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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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. 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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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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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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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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Reference of 121-98-2, 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. 121-98-2 name is Methyl 4-methoxybenzoate, 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.

General procedure: Compounds 6a-t were synthesized from substituted benzoic acid via six steps according to the literature method as described. Various substituted benzoic acids 1a-t were treated with SOCl2 to give compounds 2a-t, which were reacted with CH3OH and EtN3 in CH2Cl2 at 0 to afford compounds 3a-t. Compounds 4a-t were prepared by the reaction of compounds 3a-t, hydrazine hydrate in CH3OH under reflux condition about 5h. Subsequently, compounds 5a-t were obtained by reaction of compounds 4a-t with CS2 and KOH in CH3OH. Compounds 6a-t were obtained by the cyclization reaction of compounds 5a-t in the presence of HCl at 0-5C.

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; Li, Liangjing; Ding, Hao; Wang, Baogang; Yu, Shichong; Zou, Yan; Chai, Xiaoyun; Wu, Qiuye; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 192 – 194;,
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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. 685-88-1, name is Diethyl fluoromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of Diethyl fluoromalonate

2-fluoromalonic acid diethylester is manufactured from 2-chloromalonic acid diethylester and l,8-diazabicyclo[5,4,0]undec-7-ene- l,37HF neat at 80C, as described in example 2 of US 7,145,046. The raw product is hydrolyzed, in analogy to example 1 of DE-Offenlegungsschrift 4120704, by contacting it with NaOH in water (concentration of NaOH : 30% by weight). Resulting ethanol is removed by distillation, and the resulting solution is contacted withLewatit S 100 in the H-form (i.e. comprising acidic H+). The aqueous solution of fluoromalonic acid is mixed with toluene, and at a reduced pressure(400 mbar), a water/toluene mixture is removed.The resulting fluoromalonic acid then reacted with acetone as described by D. Davidson and S. A. Bernhard in J. Chem. Soc. 70(1948), page 3428, 1. paragraph in chapter “Experimental”. The fluoromalonic acid is suspended in acetic anhydride and concentrated sulfuric acid is added. The amounts of the reagents and starting compounds correspond to those described by Davidson et al.The acetone is added under cooling. After a post-reaction phaseof 2 hours, 5-fluoro-2,2-dimethyl-l,3-dioxane-4,6-dione can be isolated.

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SOLVAY SA; BRAUN, Max Josef; WO2013/79397; (2013); A1;,
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