Tag: M.W=200-300

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. 25542-62-5, name is Ethyl 6-bromohexanoate, This compound has unique chemical properties. The synthetic route is as follows., Safety of Ethyl 6-bromohexanoate

Example 9.1 (0321) (0322) Ethyl 2-methyl acetoacetate (29.2 mL, 0.203 mol. 1 eq), 21% sodium ethoride solution (64 mL, 0.816 mol, 4 eq), ethyl 6-bromohexanoate (34 mL, 0.192 mol, 1 eq) and ethanol (200 mL) are added and the mixture is subjected to reflux at 120 C. for 12 hours. Next, the solvent is neutralized with 1M hydrochloric acid and extraction is carried out by using chloroform and distilled water. The extracted solvent is dried under reduced pressure and purification is carried out by normal phase chromatography to obtain the target compound (36.8 g, 63.4%). (0323) Rf=0.34 (Silica gel, hexane/ethyl acetate=10:1 v/v)

According to the analysis of related databases, 25542-62-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BioActs Co., Ltd.; PARK, Jin Woo; JANG, Su-Jung; KIM, Kiwon; SHIN, Gyeong Rim; LEE, Bongkyu; (52 pag.)US2017/313883; (2017); 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. 51760-21-5, name is Dimethyl 5-bromoisophthalate, A new synthetic method of this compound is introduced below., Recommanded Product: 51760-21-5

Into a round-bottom flask were charged with dimethyl 5-bromoisophthalate (0.50 g, 1.8 mmol), barium hydroxide octahydrate (0.43 g, 1.4 mmol) and methanol (10 mL). The mixture was stirred at room temperature overnight. HCl (2 N ethyl ether solution, 10 mL) was added and the volatiles were removed under reduced pressure. The residue was purified via flash chromatography to afford the desired product as a white solid. 1H NMR (400 MHz, DMSO-d6): 13.70 (br, IH), 8.42 (t, J = 1.5 Hz, IH), 8.31- 8.24 (m, 2H), 3.90 (s, 3H).

The synthetic route of 51760-21-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; WO2009/110985; (2009); A2;,
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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. 29823-21-0, name is Ethyl 8-Bromooctanoate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H19BrO2

a) 4,5-Bis(4-methoxyphenyl)-2-phenylimidazole (7 g) (J. Med. Chem., 1974, 17, 1182-8) and ethyl 8-bromo-octanoate (9.9 g) were reacted in a method similar to Example 9. Column chromatography on silica gel eluted with a hexane:ethyl acetate gradient gave 1-(7-ethoxy-carbonylheptyl)-4,5-bis(4-methoxyphenyl)-2-phenyl-imidazole (10.3 g, 100%) as an oil. NMR d (CDCl3) 0.8-1.5 (13H, m, 5*CH2, CH3), 2.18 (2H, t, CH2 =O), 3.75 (3H, s, OCH3), 3.88 (5H, m, NCH2, OCH3), 4.1 (2H, q, CH2 OC=O), 6.7-7.7 (13H, m, ArH) ppm.

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 29823-21-0.

Reference:
Patent; SmithKline Beecham Corporation; The Johns Hopkins University; US5648373; (1997); 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. 99974-66-0, name is Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate, A new synthetic method of this compound is introduced below., name: Diethyl 3-hydroxycyclobutane-1,1-dicarboxylate

A solution of alcohol Id (3.0 g) in 200 mL of dichloromethane was treated with Dess-Martin periodinane (1.2 eq, 7.06 g). The mixture was stirred for 2 h at room temp. The reaction was quenched by addition of aq saturated sodium thiosulfate soln (100 mL). The mixture was stirred for 20 min followed by addition of aq saturated sodium bicarbonate soln (100 mL). The mixture was further stirred for 20 min and extracted with ethyl acetate (500 mL). The aqueous layer was back extracted with ethyl acetate (250 mL). The combined organic layers were washed with aq saturated sodium bicarbonate (2 x 80 mL) and brine (80 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in rotavap. The product was purified on silica gel (Biotage75-M column; gradient: 0 to 30% ethyl acetate in hexanes) to afford the product (5.14 g; 96 %) as a colorless oil.

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; SCHERING CORPORATION; WO2009/8913; (2009); A2;,
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2905-69-3, name is Methyl 2,5-dichlorobenzoate, 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. Recommanded Product: Methyl 2,5-dichlorobenzoate

Add 19.1 g of 2,5-dichlorobenzoic acid (0.1 mol) and 120 ml of methanol to the reaction flask.Add a catalytic amount of acid and reflux at 65~70 C for 8 hours.After the reaction, the excess methanol was distilled off under reduced pressure.19.2 g of methyl 2,5-dichlorobenzoate was obtained in a yield of 93.6%.The obtained methyl 2,5-dichlorobenzoate (0.094 mol) was added to the reaction flask.Add 30 g of bromine (0.19 mol) and 2.5 g of aluminum tribromide.The reaction was carried out at 50 C for 6 hours, and after the reaction was completed, it was extracted with ethyl acetate and water.After drying over anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to give 24 g of Compound 3.The yield was 90.2%.Adding the obtained compound 3 to the reaction flask,Add 60 ml of methanol and a suitable palladium catalyst and react at 80 C for 6 hours.The reaction was extracted, dried, and the solvent was evaporated under reduced pressure to give 17.1 g of Compound 4.The yield was 86%.Finally, the compound 4 was placed in a reaction flask, 100 ml of deionized water was added, and an appropriate amount of acid was added, and the reaction was carried out at 60 C for 3 hours. After the reaction was completed, it was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The final product, dicamba, 14.5 g was obtained after pressure distillation.The total yield is 65%.

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

Reference:
Patent; Jiangsu Changqing Agrochemical Co., Ltd.; Yu Guoquan; Sun Xialin; Ma Changqing; Ding Huaping; (6 pag.)CN109134232; (2019); A;,
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Reference of 53518-15-3, 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 53518-15-3 as follows.

The Schiff base was synthesized from the condensation reaction between 7-amino-4-(trifluoromethyl)coumarin (0.2684g; 1.171mmol) and 20 2-amino-3-formylchromone (0.2216g; 1.171mmol) in 16 methanol (20cm3) which was heated under reflux for 3h. The resultant yellow solution was allowed to cool to room temperature before the light yellow precipitate was filtered and washed using cold methanol and 21 petroleum ether. Yield=50%; Melting point: 239.9-244.8C; Infrared (vmax/cm-1): nu(N-H) 3242, 3093 (br), nu(C=O) 1679 (s), nu(C=N) 1610 (s), nu(C-O-C) 1334 (s); 1H NMR (d6-DMSO/298K/ppm): 10.09 (s, 1H, H11), 9.59 (s, 2H, NH2), 8.05-8.01 (dd, J=7.7Hz, J=1.7Hz, 1H, H15), 7.76-7.70 (t, J=1.5Hz, J=1.1Hz, 3H, H17), 7.48-7.33 (m, 3H, H8, H16, H18), 6.68-6.64 (dd, J=8.8Hz, J=2.2Hz, 1H, H9), 6.53-6.50 (d, J=2.2Hz, 1H, H6), 6.43 (s, 1H, H3); 13C NMR (d6-DMSO/295K/ppm): 188.42 (C13), 175.58 (C20), 165.96 (C4), 159.86 (C19), 157.05 (C2), 154.57 (C11), 153.60 (C5), 134.59 (C7), 126.22 (C9), 126.20 (C14), 125.83 (C16), 125.70 (C1), 122.70 (C17), 117.34 (C15), 112.69 (C18), 107.92 (C10), 107.86 (C8), 102.23 (C6), 99.46 (C3), 99.14 (C12); UV-Vis (Methanol, lambdamax (epsilon, M-1cm-1)): 377nm (1361), 292nm (1297), 264nm (1785), 234nm (2698); TOF-MS (m/z): Calcd: 400.0671, Found: 400.0753 [M]+, 401.0750 [M+H]+, 402.0785 [M+2H]+.

According to the analysis of related databases, 53518-15-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jadoo, Barushka; Booysen, Irvin Noel; Akerman, Matthew Piers; Rhyman, Lydia; Ramasami, Ponnadurai; Polyhedron; vol. 144; (2018); p. 107 – 118;,
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Adding a certain compound to certain chemical reactions, such as: 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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 55666-43-8, Application In Synthesis of tert-Butyl 3-bromopropanoate

To a mixture of 2-sulfanyl-5,6,7,8-tetrahydro-4-quinazolinol (0.482 g, 2.64 mmol) and potassium carbonate (0.730 g, 5.29 mmol) in acetone was added tert-butyl 3-bromopropionate (0.663 g, 3.17 mmol). The mixture was stirred at 60C for 4 h (LC-MS indicated partial conversion to desired product). The solid was filtered off, and the solution was concentrated. The residual material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 50% EtOAc in hexane, to provide tert- butyl 3-((4-oxo-3,4,5,6,7,8-hexahydroquinazolin-2-yl)thio)propanoate (0.132 g, 0.425 mmol, 16.09 % yield) as white solid. lH NMR (400 MHz, DMSO-i/6) delta ppm 12.40 (br. s., 1 H) 3.24 (t, J=6.70 Hz, 2 H) 2.64 (t, J=6.75 Hz, 2 H) 2.42 – 2.49 (m, 2 H) 2.28 (br. s., 2 H) 1.60 – 1.78 (m, 4 H) 1.41 (s, 9 H). m/z (ESI) 31 1.2.

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Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John L.; CHAKKA, Nagasree; DIMAURO, Erin F.; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Xin; WO2014/36022; (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. 6279-86-3, name is Triethyl methanetricarboxylate, This compound has unique chemical properties. The synthetic route is as follows., 6279-86-3

1b) 6-Hydroxy-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone; A mixture of the compound from example 1(a) (0.342 g, 1.63 mmol), triethyl methanetricarboxylate (0.755 g, 3.25 mmol), methanolic sodium methoxide (0.378 mL of a 4.37 M solution, 1.65 mmol) and ethanol (3 mL) was stirred in a microwave reactor at 160 C. for 0.5 h, then cooled and poured into 1M aqueous hydrochloric acid (20 mL). The mixture was extracted with ethyl acetate, and the extracts washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was chromatographed (silica gel, 5-10% methanol/dichloromethane) to give the title compound (0.320 g, 44%) as a foam. 1H NMR (400 MHz, DMSO-d6) delta ppm 5.05 (s, 2 H) 5.50 (s, 1 H) 6.87 (m, 2 H) 7.18-7.26 (m, 3 H) 7.36-7.43 (m,4H) 7.49 (m, 1 H) 11.64 (s, 1 H).

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; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
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Synthetic Route of 39503-58-7, These common heterocyclic compound, 39503-58-7, name is Methyl 5-bromo-2-methoxy-4-methylbenzoate, 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.

A solution of S2(12.8g, 48.8 mmol), N-bromosuccinimide (9.68 g, 54.78 mmol, 1.1 eq.), azobisisobutyronitrile (1.64 g, 9.96 mmol, 0.2 eq.) in carbon tetrachloride was heated at 70 C. After 14 h, solvent was removed and the residue purified by flash chromatography (Si02, 1 :9 ethyl acetate/hexanes) to afford S3 (13.92 g, 71.3 %) as a white amorphous solid. 1H NMR (500 MHz, CDC13) delta 7.91 (s, 1H), 7.60 (s, 1H), 7.00 (s, 1H), 3.99 (s, 3H), 3.90 (s, 3H).13C NMR (125 MHz, CDC13) delta 164.7, 159.0, 144.8, 135.5, 123.0, 114.6, 109.5, 56.7, 52.7, 39.3. HRMS (ESI+) m/z [M + H+] calcd for C10H11Br203, 336.9075, found 336.9079.

The synthetic route of 39503-58-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
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These common heterocyclic compound, 6279-86-3, name is Triethyl methanetricarboxylate, 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. Safety of Triethyl methanetricarboxylate

10129] 14.5 parts (62.4 mmol) of triethyl carboxymalonate,11.4 parts (76.4 mmol) of 5-amino-2-benzimidazolinone and0.138 part (0.626 mmol) of 2,6-di-tert-butyl-p-cresol weredissolved in 141 parts (1.93 mol) of N,N-dimethylformamide, and reacted under heating and stirring at 800 C. for 6hours. After the reaction, N,N-dimethylformamide was distilled away under reduced pressure, and 300 parts (16.7 mol) of water was added to the obtained residue. The deposit was filtered to thereby obtain the intermediate (4).

The synthetic route of Triethyl methanetricarboxylate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANON KABUSHIKI KAISHA; CANON FINETECH INC.; Kubo, Haruko; Ueno, Suzuka; Chizuwa, Junko; Yamamoto, Tomoya; Itabashi, Hitoshi; Terui, Yuhei; Yoshida, Yu; Murai, Yasuaki; Toyoda, Takayuki; (26 pag.)US2016/130233; (2016); A1;,
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