Month: August 2021

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. 5202-89-1, name is Methyl 2-amino-5-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8ClNO2

Methyl 2-amino-5-chlorobenzoate (compound A) (4.0 g) was dissolved in anhydrous methylene chloride (80.0 ml). Subsequently, pyridine (2.8 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (5.0 g) were added to the solution at room temperature, and the mixture was stirred at that temperature for 2 hr. After the completion of the reaction, distilled water was added thereto, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution and saturated brine, was dried over sodium sulfate, and was then concentrated to give methyl 5-chloro-2-[3-(chloromethyl)benzoyl]aminobenzoate as a useful intermediate (3.32 g, yield 100%).

According to the analysis of related databases, 5202-89-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KIRIN BEER KABUSHIKI KAISHA; EP1614676; (2006); A1;,
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Related Products of 653-92-9, 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 653-92-9 as follows.

2-bromo-4-fluoro-1-nitrobenzene(185.16mg, 0.842mmol) to was added Pd 2 dba 3 (23.12mg, 0.025mmol) and copperpowder a (271mg, 4.26mmol). Dimethyl sulfoxide (2.3 ml) and methyl2-bromo-4-fluorobenzoate (0.122ml, 0.842mmol) was added and the mixture wasstirred vigorously for 2 hours at 100 C. The mixture was cooled to roomtemperature, diluted with ethyl acetate (20 ml), and filtered. The filtrate waswashed with water, dried (anhydrous Na 2 SO 4), and concentrated to give ayellow oil (279.8mg). It was used in the preparation of Example 38b withoutpurification this oil.

According to the analysis of related databases, 653-92-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; ENANTA PHARMACEUTICALS INCORPORATED; KU, YIYIN; MCDANIEL, KEITH F; CHEN, HUI-JU; SHANLEY, JASON P; KEMPF, DALE J; GRAMPOVNIK, DAVID J; SUN, YING; LIU, DONG; GAI, YONGHUA; OR, YAT SUN; WAGAW, SEBLE H; ENGSTROM, KEN; GRIEME, TIM; (87 pag.)JP5902123; (2016); B2;,
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Reference of 4911-54-0, 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 4911-54-0 as follows.

43.7 g (0.2 mol) of 2-chloro-4-fluoro-5-nitrobenzaldehyde oxime was dissolved in 150 ml of N, N-dimethylformamide, the temperature was raised to 30 C, and 32 g ( 0.24 mol) of NCS to form a light yellow solution, and the reaction was held at 35 C for 1 hour. Lower to room temperature, add 300 ml of dichloromethane, then wash twice with 1N hydrochloric acid, twice with saturated brine, dry over anhydrous magnesium sulfate, suction filter, reduce the dichloromethane solution to 0-5 C, and add 42.6 g A mixed solution of 0.3 mol) of ethyl 4-methyl-4-pentenoate and 31 g (0.3 mol) of triethylamine was reacted while maintaining the temperature for 1 hour. The organic phase was washed with 1N hydrochloric acid and saturated brine in this order, and the organic phase was dried over anhydrous magnesium sulfate. After desolvation, column chromatography (ethyl acetate: petroleum ether = 1: 3) gave 41.9 g of a pale yellow solid.

According to the analysis of related databases, 4911-54-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shenyang Sinochem Pesticide Chemical Research And Development Co., Ltd.; Yang Jichun; Guan Aiying; Cui Dongliang; Wu Jiao; Yan Kecheng; Liu Changling; (13 pag.)CN110818699; (2020); A;,
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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. 1117-71-1, name is Methyl 4-bromobut-2-enoate, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of Methyl 4-bromobut-2-enoate

Trithylamine (37.5 ml, 0.27 mol, 2.8 equiv) was dissolved in THF (100 ml), and dimethylamine hydrochloride (9.3 g, 0.114 mol, 1.2 equiv) was added. Methyl 4- bromocrotonate (2Og, 85% purity, 0.095 mol, 1.00 equiv) in 100 ml of THF was added drop- wise to the resulting solution at room temperature while stirring. The reaction mixture was allowed to react overnight at room temperature. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure to give yellow oil. The oil was dissolved in 50 ml of isopropanol, and hydrogen chloride was added until pH 2.0 was reached. The white solid was formed and filtered and dried to give 7.1g product. MS (ESI) m/z: 563 (M+l).

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 1117-71-1.

Reference:
Patent; MEDOLUTION LIMITED; ZHANG, Dawei; WO2010/151710; (2010); A2;,
Ester – Wikipedia,
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Synthetic Route of 6279-86-3, A common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, molecular formula is C10H16O6, 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 mixture of triethyl 1,1, 2-ethanetricarboxylate (3.51 mL, 15.30 mmol) and 2- (4-nitrophenyl)- ethanimidamide hydrochloride (46.95 g, 217.72 mmol) in anhydrous MeOH (300 mL) at room temperature was added NaOMe (3.8. 82 g, 718.49 mmol) and the resulting suspension was refluxed for 16 hours. After cooling to room temperature, the reaction mixture was chilled to 0C, acidified with 6N HCI, and the separated solids collected by suction and rinsed with cold water. Drying under high vacuum at 45C for 6 hours then gave methyl [4, 6-dihydroxy-2- (4-nitrobenzyl)- pyrimidin-5-yl] acetate (56.48 g, 81% yield) as a pale white powder.

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; BAYER HEALTHCARE AG; WO2005/73234; (2005); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 3196-15-4, name is Methyl 2-bromobutyrate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 3196-15-4

DMF (3 mL) mixed solution of 5-chloro-4- (6-fluoro-2-mercaptobenzothiazole-5-yl) -1,2-tetramethylene-4-pyrazoline-3-one (240 mg, 0.67 mmol), cesium carbonate (264 mg, 1.2mmol) was stirred for 10 min, then 2-bromo-butyric acid methyl (107muL, 1.2mmol) was added and the mixture was stirred at room temperature for 24 hours. After the reaction, water was added to the reaction solution and extracted with chloroform. The organic layer was dried anhydrous magnesium sulfate and concentrated under reduced pressure. the obtained crude product was purified by eluting through silica gel column chromatography (ethyl acetate) to give a yellow oil of 2-[{5-(5-chloro-3-oxo-1,2-tetramethylene pyrazoline-4-yl)-6-fluoro-benzothiazol-2-yl} thio] methyl butanoate (171 mg, yield: 56%).

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 3196-15-4.

Reference:
Patent; SAGAMI CHEMICAL RESEARCH INSTITUTE; KAKEN PHARMACEUTICAL COMPANY LIMITED; KOBAYASHI, OSAMU; TAKATSUNA, REIKO; NIIKURA, NAOKO; MATSUKAWA, TOMOKO; NAKAMURA, SHINJI; HIRAI, KENJI; KOCHI, SHINICHIRO; KAWANISHI, NAOKI; YAMADA, OSAMU; (31 pag.)JP2016/56156; (2016); A;,
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Electric Literature of 711-01-3, 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. 711-01-3, name is Methyl adamantane-1-carboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A suspension of Lithium Aluminium Hydride (LAH) (6.41 g, 168 mmol) in THF (250 mL) was cooled to 0 C and methyl adamantane-l-carboxylate (21.8 g, 1 12 mmol) in 50 mL of THF was added slowly at 0 C for 30 minutes. After complete addition, the reaction mixture was stirred at room temperature (RT) for 45 minutes. EtOAc (100 mL) was added slowly at 0 C followed by slow addition of water (20 mL) at 0 C. Reaction mixture was filtered and filtrate was dried over anhydrous sodium sulphate, solvent was distilled out and dried to afford the pure product (17 g, 91% yield).

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

Reference:
Patent; ORCHID RESEARCH LABORATORIES LTD.; RAJAGOPAL, Sridharan; THANGAPAZHAM, Selvakumar; PAUL-SATYASEELA, Maneesh; BALASUBRAMANIAN, Gopalan; SHAKTI SINGH, Solanki; KUPPUSAMY, Bharathimohan; KACHHADIA, Virendra; CHENNIAPPAN, Vinoth Kumar; GANESAN, Karthikeyan; NARAYANAN, Shridhar; WO2011/58582; (2011); 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. 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;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7335-27-5, name is Ethyl 4-chlorobenzoate, 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 7335-27-5, name: Ethyl 4-chlorobenzoate

General procedure: In a glove box, add a ruthenium complex Ia (0.3 to 0.7 mg, 0.0002 to 0.001 mmol) to a 300 mL autoclave,Potassium methoxide (35-700 mg, 0.5-10 mmol), tetrahydrofuran (4-60 mL), and ester compounds (10-200 mmol).After sealing the autoclave, take it out of the glove box and fill it with 50 100atm of hydrogen.The reaction kettle was heated and stirred in an oil bath at 100 C for 10 to 336 hours.After the reaction kettle was cooled in an ice-water bath for 1.5 hours, the excess hydrogen was slowly released.The solvent was removed from the reaction solution under reduced pressure, and the residue was purified with a short silica gel column to obtain an alcohol compound. The results are shown in Table 5.

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; Zhejiang Zhongke Chuangyue Pharmaceutical Co., Ltd.; Ding Kuiling; Tang Yitian; Han Zhaobin; (55 pag.)CN110357923; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 2475-80-1, 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 2475-80-1 as follows.

To 2-nitro-5-methoxy-benzoic acid (4 g, 20.3 mmol) in 35 mL of methanol was added trimethylsilyldiazomethane (35 mL, 70 mmol, 2 M in dichloromethane) at RT dropwise. The mixture was stirred at RT for 10 h. To the mixture was added several drops of acetic acid. The resulting solution was concentrated in vacuo to give a brown solid. To this intermediate was added 150 mg of Pd/C (10%). The mixture was stirred under 40 psi of hydrogen gas for 5 h. The mixture was filtered and washed with dichloromethane. The filtrate was concentrated m vacuo to give a dark red oil. To this aniline intermediate were added 30 mL of ethanol and 5 mL of concentrated HCl. To this mixture at 00C was dropwise added a solution of sodium nitrite (5.6 g, 81.2 mmol) in 15 mL of water to form the diaza salt. After 1 h at 00C, to the resulting dark red solution was slowly added sodium azide (8.6 g, 132 mmol) in 15 mL of water. After 1 h at O0C, the slurry was filtered and washed with saturated sodium carbonate solution and water to give the azide as a red solid. The same DIBALH reduction procedure as described above gave the benzyl alcohol as a dark red oil. To this oil in 100 mL of dichloromethane was added PCC (8 g) at O0C. The mixture was stirred at RT for 4 h and purified by Biotage (2-20% ethyl acetate in hexane) to give the aryl azide aldehyde intermediate as a light yellow solid. To a solution of this intermediate (1.1 g, 6.3 mmol), malononit?le (423 mg, 0 40 mL, 6 4 mmol) and 15 mL of dichloromethane was added a solution of pipe?dine (145 mg, 0.17 mL, 1.7 mmol) in 5 mL of dichloromethane. After 2 h at RT, the mixture was filtered and the solid was washed with dichloromethane to give the tricycle as a brown solid. To this intermediate (0.66 g, 2 9 mmol) m 10 mL of DME and 20 mL of dichloromethane was added DIBALH (7.04 mL, 7.04 mmol, 1 M in hexane) at – 780C The mixture was stirred at -780C for 3 days. The mixture was then quenched with water and saturated Rochelle’s salt (200 mL) at -780C. The aqueous layer was then extracted with 30% isopropyl alcohol in chloroform. The combined fractions were dried with sodium sulfate and concentrated in vacuo. The residue was purified by RP-HPLC to give a light yellow solid A similar homologation sequence described in EXAMPLE 86 gave the intermediate enamide. To a slurry of this enamide (18 mg) in 150 mL of methanol was added p-toluenesulfonylhydrazide (400 mg). The mixture was heated at reflux overnight. After removing the solvent, the residue was purified by RP-HPLC to give a pale yellow solid. Following the similar hydrolysis and demethylation procedures as described for the preparation of EXAMPLE 86, the desired compound was obtained as a white solid 1H NMR (CD3OD, 500 MHz) delta 8.50 (1H, d), 8.47 (1H, d), 8.00 (1H, d), 7.84 (1H, s), 7.52 (1H, t), 7.34 (1H, dd), 7.29 (1H, d), 7.11 (1H, t), 3.50 (2H, t), 3.06 (2H, t); LCMS m/z 378 (M++1).

According to the analysis of related databases, 2475-80-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/52555; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics