Author: Jessica.F

1732-08-7, name is Dimethyl pimelate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of Dimethyl pimelate

To a 500 ml four-necked flask equipped with a stirring, a thermometer, a reflux condenser, and a constant pressure dropping funnel, 100 g of chloroform, 18.8 g (0.1 mol) of dimethyl 1,7-pimelate, and 0.6 g of 40 wt% were added. Hydrobromic acid, 72.0 g of bromine and 50 g of chloroform were added dropwise at 30-35 C. After the completion of the dropwise addition, the reaction was stirred at 30-35 C for 7 hours, cooled to 20-25 C, and purged with nitrogen for 2 hours. 17 wt% ammonia water, stirring reaction at 60-65 C for 6 hours, then, cooling to 20-25 C, adding 20 g of 30 wt% hydrogen peroxide, stirring at 30-35 C for 4 hours, adding 45 g of 20 wt% aqueous sodium hydroxide solution, The reaction was stirred at 30-35 C for 4 hours, layered, and the organic phase was washed twice with water. Each time 20 g of water, the aqueous phase is combined, the pH of the aqueous phase is adjusted to 2.5-2.0 with hydrochloric acid, filtered, and dried to obtain 15.1 g of a white solid 2,6-pyridinedicarboxylic acid, the liquid phase purity is 99.5%, and the product yield is 90.4%. .

The synthetic route of 1732-08-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Xin Fa Pharmaceutical Co., Ltd.; Ju Lizhu; Zhang Mingfeng; Lv Qiangsan; Qi Yuxin; (7 pag.)CN110229096; (2019); A;,
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Application of 179688-27-8,Some common heterocyclic compound, 179688-27-8, name is Ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate, molecular formula is C15H23NO6, 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.

EXAMPLE 62 N’-[2-Carbethoxy-4,5-bis(2-methoxyethoxy)phenyl]-N,N-dimethylformamidine To a stirred solution of 15.7 g (50 mmol) of ethyl 2-amino-4,5-bis(2-methoxyethoxy)benzoate (WO-96130347) in 50 ml of DMF at 0 C. was added phosphorous oxychloride (5.6 ml, 60 mmol) during 15 m. The resulting solution was heated at 55 C. for 45 m, cooled, diluted with methylene chloride, and treated at 0 C. with 200 ml of N/1 sodium hydroxide during 2 m. The organic layer was separated and washed at 0 C. with water. The solution was dried and evaporated with added toluene present to give 18.4 g of amber oil; NMR (CDCl3) delta6 3.02 (s, Me2N).

The synthetic route of 179688-27-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6288082; (2001); B1;,
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Application of 35005-25-5, The chemical industry reduces the impact on the environment during synthesis 35005-25-5, name is Isopropyl 3-aminobenzoate, I believe this compound will play a more active role in future production and life.

3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanoic acid (1.0 equiv) and isopropyl 3-aminobenzoate (1.2 equiv) were mixed in DMF, and the resulting mixture was added to HATU (1.5 equiv) and DIPEA (1.5 equiv). The reaction mixture was stirred overnight at room temperature and concentrated under reduced pressure, and the obtained residue was diluted with EtOAc and washed with water and brine. An organic layer was collected and dehydrated with anhydrous MgSO4, and concentrated under reduced pressure. The concentrate was purified by silica gel column chromatography, thereby obtaining isopropyl 3-(3-(4-(2,4,4-trimethylpentan-2-yl)phenoxy)propanamido)benzoate (transparent liquid, 0.06 g, 26.5% yield). (0364) 1H-NMR (500 MHz, CDCl3) 7.99 (brs, 2H), 7.93 (d, J=7.0 Hz, 1H), 7.79 (d, J=7.0 Hz, 1H), 7.41 (t, J=8.0 Hz, 1H), 7.32 (d, J=9.0 Hz, 2H), 6.89 (d, J=8.0 Hz, 2H), 5.25 (m, 1H), 4.35 (t, J=6.0 Hz, 2H), 2.87 (t, J=6.0 Hz, 2H), 1.72 (s, 2H), 1.38 (d, J=6.5 Hz, 6H), 1.36 (s, 6H), 0.72 (s, 9H); 13C-NMR (125 MHz, CDCl3) delta 169.2, 165.7, 155.6, 143.4, 137.9, 131.6, 129.1, 127.3, 125.3, 124.3, 120.6, 113.8, 68.6, 64.1, 56.9, 38.0, 37.8, 32.3, 31.8, 31.7, 21.9.

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, Isopropyl 3-aminobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DONGGUK UNIVERSITY GYEONGJU CAMPUS INDUSTRY-ACADEMY COOPERATION FOUNDATION; KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY; Lee, Kyeong; Won, Mi Sun; Ban, Hyun Seung; Kim, Minkyoung; Kim, Bo Kyung; (40 pag.)US2020/31764; (2020); 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. 2216-45-7, name is 4-Methylbenzyl acetate, A new synthetic method of this compound is introduced below., SDS of cas: 2216-45-7

General procedure: A mixture of benzonitrile (5 mmol), benzyl acetate (6 mmol),and Fe(ClO4)3·H2O (5 mol%) was placed in a round-bottomedflask. Then, the reaction mixture was heated at 80 C for 5 h.After completion of the reaction monitored by thin layer chromatography(TLC), water (10 mL) was added, and the reactionmixture was extracted with ethyl acetate (3 × 20 mL). Theorganic layers were collected, combined, washed with water(3 × 20 mL), dried with anhydrous Na2SO4, and concentratedunder vacuum. The pure product was obtained by directlypassing through a silica gel (200-300 mesh) column to give awhite powder a (0.91 g, 87% yield)..

The synthetic route of 2216-45-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Feng, Chengliang; Yan, Bin; Yin, Guibo; Chen, Junqing; Ji, Min; Synlett; vol. 29; 17; (2018); p. 2257 – 2264;,
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These common heterocyclic compound, 63243-76-5, name is Ethyl 2-amino-5-bromobenzoate, 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. HPLC of Formula: C9H10BrNO2

[00384] The mixture of 2-amino-5-bromo-benzoic acid ethyl ester (3.0 g, 13.16 mmol) and (0979) cyclopropanecarbonitrile (2.6 g, 39.47 mmol) in 6 M HCl/dioxane (60 mL) was stirred at reflux overnight. The solid was filtered, dried in vacuum to give 6-bromo-2-cyclopropyl-quinazolin-4-ol (3.3 g, yield: 95%) as crude product. MS: m/z 249.1 (M+H+).

The synthetic route of Ethyl 2-amino-5-bromobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HEDRICK Michael P.; HERSHBERGER Paul M.; MALONEY Patrick R.; PEDDIBHOTLA Satyamaheshwar; PINKERTON Anthony B.; WO2015/200534; A2; (2015);,
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Synthetic Route of 87661-20-9, A common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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.

Step 1: A solution of n-butyl lithium in hexane (1.4M, 45.75 mL, 0.07 mol) was added drop wise to a solution of freshly distilled diisopropylamine (10.2 mL, 0.06 mol) in dry THF (200 mL) at -60 C. under nitrogen atmosphere. The reaction mixture was slowly warmed to -20 C. and stirred for 30 min. The reaction mixture was re-cooled to -60 C. and cyclopropanecarboxylic acid tert-butyl ester (9.48 g, 0.06 mol) added drop wise over a period 30 min. Reaction mixture was slowly warmed to -20 C. and stirred for 30 min. To the re-cooled (-60 C.) reaction mixture was added drop wise 1,10-dibromodecane (20.0 g, 0.06 mol) in dry THF (20 mL) and DMPU (1.79 g, 0.01 mol). Then the temperature was allowed to reach room temperature and stirred at same temperature over a period of 16 h The resulting reaction mixture was quenched with saturated NH4Cl (500 mL) at 0 C. and the reaction mixture was extracted with ethyl acetate (300 mL¡Á3). The organic phases were combined, dried over anhydrous Na2SO4 and volatiles were evaporated under reduced pressure to yield a pale yellow liquid which was purified through silica gel (230-400) column (0.5% ethyl acetate in petroleum ether) to give product as colorless oil 8.0 g (33%).1H NMR (300 MHz, DMSO-d6) delta (ppm): 0.62-0.64 (m, 2H), 0.94-0.98 (m, 2H), 1.25 (bs, 12H), 1.37 (s, 9H), 1.39-1.43 (m, 4H), 1.73-1.80 (m, 2H), 3.52 (t, J=6.6 Hz, 2H).

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; KAREUS THERAPEUTICS, SA; US2012/71528; (2012); 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. 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate, A new synthetic method of this compound is introduced below., HPLC of Formula: C10H8Br2O4

Example 11Production of Compound 15 A mixed liquid of methyl p-dibromoterephthalate (Compound 1)(10.6 g, 30.0 mmol) synthesized according to the method of a literature (Macromolecules, 1999, 32, 2455), Compound 15 (made by Sigma-Aldrich Corp.)(24.8 g, 66.0 mmol), PdCl2 (dppf).CH2Cl2 (2.45 g, 3.00 mmol), potassium carbonate (13.7 g, 13.7 mmol), water (60 mL) and THF (1.2 L) was refluxed under a nitrogen atmosphere for 16 hours. After the reaction mixed liquid was allowed to cool to room temperature, water was added to the reaction mixed liquid, and the reaction mixed liquid was subjected to extraction with chloroform. The obtained organic layer was dried with sodium sulfate, and filtered, and thereafter, the solvent was distilled out under reduced pressure. The obtained mixture was separated and refined by a silica gel column chromatography to obtain Compound 16 (7.89 g, 15.0 mmol) in a yield of 50%.The physical properties of Compound 16 were as follows.1H-NMR (CDCl3, delta ppm): 7.81 (s, 2H), 7.06 (d, 2H), 6.97-7.04 (m, 4H), 6.70 (d, 2H), 3.64 (s, 6H), 2.80 (t, 4H), 1.56-1.63 (m, 4H), 1.32-1.41 (m, 12H), 0.90 (t, 6H)

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; Sumitomo Chemical Company Limited; US2011/87034; (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. 2905-69-3, name is Methyl 2,5-dichlorobenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 2905-69-3

EXAMPLE 2 Dehalogenation of Methyl 2,5-Dichlorobenzoate A 50-mL round-bottom flask was equipped with a magnetic stir bar, reflux condenser, thermometer, nitrogen inlet, and heating mantle attached to a temperature controller. The flask was charged with methyl 2,5-dichlorobenzoate (5.0 g, 24 mmol) and copper powder (3.04 g, 48 mmol). Propionic acid (10 mL) and xylenes (15 mL) were added, and the resulting mixture was heated to 130-135 C. The reaction was monitored by GC analysis and was judged to be complete when the starting material was no longer detectable (3 hours). The reaction mixture was cooled to room temperature and filtered; the solids were washed with xylenes. The filtrates were blue-green. The filtrates were combined and washed with 1M hydrochloric acid solution until the blue-green color disappeared. The resulting yellow organic layer was washed with water and dried over sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was dried under vacuum, yielding 3.93 g of methyl 3-chlorobenzoate as a pale yellow oil.

The synthetic route of 2905-69-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Company; US5886210; (1999); A;,
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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. 41727-48-4, name is Methyl 4-amino-3,5-dichlorobenzoate, A new synthetic method of this compound is introduced below., Safety of Methyl 4-amino-3,5-dichlorobenzoate

Example 45 Preparation of methyl 3,5-dichloro-4-cyanobenzoate (C77) Copper(I) cyanide (7.41 g, 82.7 mmol) was added to acetonitrile and heated to 80 C. for 30 minutes. tert-Butyl nitrite (10.5 g, 102 mmol) was added followed by methyl 4-amino-3,5-dichloro-benzoate (14.0 g, 63.6 mmol) in acetonitrile (200 mL) and the reaction mixture was stirred at 80 C. for 30 minutes. The reaction mixture was poured into an ammonia solution and extracted with petroleum ether to provide the title compound as an off-white solid (7.00 g, 43%): mp 98-101 C.; 1H NMR (400 MHz, CDCl3) delta 8.12 (s, 2H), 3.98 (s, 3H); ESIMS m/z 229 ([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; Dow AgroSciences LLC; LePlae, JR., Paul R.; Barton, Thomas; Gao, Xin; Hunter, Jim; Lo, William C.; Boruwa, Joshodeep; Tangirala, Raghuram; Watson, Gerald B.; Herbert, John; (147 pag.)US2017/210723; (2017); 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. 1150164-80-9, name is Ethyl 2,2-difluoro-2-(2-methoxyphenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 2,2-difluoro-2-(2-methoxyphenyl)acetate

General procedure: To a solution of an appropriate ethyl alpha,alpha-difluoroaryl acetate (1.0 eq.) in MeOH (0.33 M) was added 1 M aq. K2CO3 (3.0 eq.). The reaction mixture was stirred at room temperature for 12 h before diluting with Et2O. The reaction mixture was extracted with aq. NaHCO3 (sat., 3x). The combined aqueous layers were acidified to pH 1 and extracted with Et2O (3x), then the combined organic phases were washed with brine, dried over MgSO4 and concentrated in vacuo. Products were purified by washing with n-pentane.

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 1150164-80-9.

Reference:
Article; Verhoog, Stefan; Pfeifer, Lukas; Khotavivattana, Tanatorn; Calderwood, Samuel; Collier, Thomas Lee; Wheelhouse, Katherine; Tredwell, Matthew; Gouverneur, Veronique; Synlett; vol. 27; 1; (2016); p. 25 – 28;,
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