Author: Jessica.F

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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Related Products of 174403-69-1, 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. 174403-69-1, name is Methyl 4-fluoro-2-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of pyrazole (100 mg, 1.47 mmol), methyl 4-fluoro-2-methylbenzoate (123.51 mg, 0.73 mmol) and potassium carbonate (609.0 mg, 4.41 mmol) in N,N-dimethylformamide (5 mL) was stirred at 60 C for 16 h. The reaction was poured into water (5 mL) and extracted with EtOAc (20 mL). The organic extract was washed with water (20 mL x 2) and brine (10 mL), dried over Mg504 and concentrated. The residue was purified by prep-TLC (33% ethyl acetate in petroleum ether, Rf = 0.3) to afford methyl 2-methyl-4-(1H-pyrazol-1-yl)benzoate (50 mg, 15.7% yield) as a white solid. LCMS (Method 5-95AB): tR =0.732 mi [M + Hj = 216.9.

The chemical industry reduces the impact on the environment during synthesis Methyl 4-fluoro-2-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; RQX PHARMACEUTICALS, INC.; GENENTECH, INC.; CHEN, Yongsheng; SMITH, Peter Andrew; ROBERTS, Tucker Curran; HIGUCHI, Robert I.; PARASELLI, Prasuna; KOEHLER, Michael F. T.; SCHWARZ, Jacob Bradley; CRAWFORD, James John; LY, Cuong Q.; HANAN, Emily J.; HU, Huiyong; YU, Zhiyong; (424 pag.)WO2017/84630; (2017); A1;,
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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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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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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. 61644-18-6, name is Chloromethyl isobutyrate, A new synthetic method of this compound is introduced below., Recommanded Product: 61644-18-6

General procedure: To a solution of Compound 54B (150 mg, 0.24 mmol) in DMF (10 mL) was added chloromethyl isobutyrate (36 mg, 0.24 mmol) and Na2CO3 (50 mg, 0.48 mmol). The reaction mixture was stirred at 50 C for 3 hour. After cooling down to room temperature, the mixture was diluted with water (50 mL) and extracted with ethyl acetate (20 mL x 3). The combined extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to furnish Compound 54C. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.

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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
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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 2967-93-3 as follows. category: esters-buliding-blocks

Step 2; Preparation of 2-Fluoro-5-formyl-benzoic acid methyl ester; Add Af-bromosuccinimide (2.46 g, 13.86 mmol) and benzoyl peroxide (0.152 g, 0.630mmol) to a solution of 2-fluoro-5-methyl-benzoic acid methyl ester (1.06 g, 6.30 mmol)in carbon tetrachloride (50 mL). Heat the mixture at reflux for 4 h. Cool the mixture toroom temperature and wash with saturated aqueous sodium bicarbonate solution (10 mL)and brine (10 mL). Dry the organic layer over anhydrous sodium sulfate, filter, andconcentrate under reduced pressure. Dissolve the resulting residue in dimethylsulfoxide(30 mL) and heat at reflux for 16 h. Cool the mixture to room temperature and dilutewith water (100 mL) and ethyl acetate (100 mL). Extract the aqueous layer with ethylacetate (3 x 100 mL). Wash the combined organic layers with water (3 x 100 mL),followed by brine (100 mL). Dry the organic layer over anhydrous sodium sulfate, filterand concentrate. Purify the residue by chromatography over silica gel, eluting withhexanes/ethyl acetate (80:20), to provide the title compound as a tan solid (0.228 g, 20%).

According to the analysis of related databases, 2967-93-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; WO2006/2342; (2006); A1;,
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Some common heterocyclic compound, 14920-81-1, name is Methyl 2,6-dimethylbenzoate, molecular formula is C10H12O2, 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. Formula: C10H12O2

General procedure: To a flame-dried 250 mL round-bottom flask under argon wereadded 4 (8.02 g, 28.4 mmol, 1 equiv), TMEDA (8.71 mL, 58.2mmol, 2.05 equiv), and anhydrous n-hexane (28 mL). Theresulting solution was cooled in an ice bath and sec-butyllithium(1.4 M solution in cyclohexane, 42.0 mL, 58.2 mmol, 2.05equiv) was added dropwise. The ice bath was removed and thereaction mixture was stirred at room temperature for 4 h. Thereaction was cooled to -78 C and a solution of methyl 2,4,6-trimethylbenzoate (5.11 g, 28.7 mmol, 1.01 equiv) in anhydrousn-hexane (28 mL) was added slowly via cannula. After the addition,the mixture was allowed to slowly warm to room temperatureand stirred for 12 h. The reaction was quenched with water(25 mL) and the biphasic mixture was stirred vigorously for 30min. The mixture was diluted with Et2O (100 mL) and the layerswere separated. The organic layer was washed with water(2 × 150 mL) and brine (1 × 150 mL). The organic layer wastransferred to a 250 mL round-bottom flask equipped with astir bar. To the vigorously stirred solution was added conc. HCl(12 mL), resulting in a bright-yellow precipitate. The suspensionwas stirred vigorously for 30 min then diluted with water (150mL). The layers were separated and the organic layer wasextracted with water (3 × 150 mL or until the washings becomecolorless). To the combined aqueous layers was added solidNaBF4 (9.35 g, 85.2 mmol, 3 equiv), resulting in a bright-yellowprecipitate. The resulting suspension was extracted withdichloromethane (3 × 150 mL or until the washings become colorless).To the combined organic layers was added HBF4·Et2Ocomplex (3.46 mL, 28.4 mmol, 1 equiv). The solution wasswirled to achieve homogeneity then washed with water(1 × 100 mL) and aq. NaBF4 (1 M, 1 × 100 mL). The organic layerwas dried over solid NaBF4, filtered, and concentrated to dryness.The residue was purified by trituration with hexanes andfiltered. The solid was rinsed with n-pentane and dried in vacuoto give xanthylium 3 (10.6 g, 21.3 mmol, 75% yield) as a yelloworangesolid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14920-81-1, its application will become more common.

Reference:
Article; White, Alexander R.; Wang, Leifeng; Nicewicz, David A.; Synlett; vol. 30; 7; (2019); p. 827 – 832;,
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Synthetic Route of 39552-81-3, 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 39552-81-3 as follows.

EXAMPLE 3 N-(4-Methoxycarbonylmethylphenyl)-L-glutamine: Compound (3) Following the procedure described in (a) of Example 1, 11.14 g (0.03 mole) of N-carbobenzoxy-L-glutamic acid alpha-benzyl ester was reacted with 4.96 g (0.03 mole) of methyl p-aminophenylacetate to give 13.38 g (88% yield) of an intermediate. The intermediate was dissolved in 500 ml of tetrahydrofuran, 200 ml of methanol and 100 ml of water. To the solution was added 0.5 g of palladium black and the mixture was subjected to hydrogenation at atmospheric pressure to give 6.09 g (79% yield) of N-(4-methoxycarbonylmethylphenyl)-L-glutamine, m.p. 183.3-184.2 C. [alpha]D25 =+29.2 (c=1 2 N HCl)

According to the analysis of related databases, 39552-81-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsubishi Chemical Industries Ltd.; Nippon Shinyaku Co., Ltd.; US4439448; (1984); A;,
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Electric Literature of 581065-95-4, 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. 581065-95-4, name is tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, This compound has unique chemical properties. The synthetic route is as follows.

Example 9: Preparation of Compounds 10a and 10b [00172] Compound 8 (1.0 g, 1.97 mmol) was dissolved in DMF (25 mL) and Et3N (1.37 mL, 9.87 mmol) and cooled to 0 C. Then TSTU (593 mg, 1.97 mmol) was added and the reaction was stirred at 0 C for 30 minutes. A solution of the appropriate pegylated amine (2.07 mmol) in chloroform (10 mL) was added dropwise at 0 C and the reaction was allowed to warm to room temperature and stir for 12 hours. The reaction was concentrated and the -Bu ester of lOa/lOb was purified by silica gel chromatography (acetonitrile/methanol). The purified -Bu ester of lOa/lOb was dissolved in dichloro methane (20 mL) and TFA (5 mL) was added at 0 C. The reaction was stirred at room temperature overnight. The reaction was concentrated and dried under reduced pressure to give pure lOa/lOb.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BIOTIUM, INC.; MAO, Fei; MCGARRAUGH, Patrick, Gordon; MADRID, Alexis, Spain; LEUNG, Wai-Yee; ROBERTS, Lori, M.; (104 pag.)WO2016/69922; (2016); 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. 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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