Tag: M.W=100-200

Synthetic Route of 121-98-2,Some common heterocyclic compound, 121-98-2, name is Methyl 4-methoxybenzoate, molecular formula is C9H10O3, 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.

General procedure: A solution of methyl 4-tert-butylbenzoate (5.15 g, 26.8 mmol) and hydrazine monohydrate (1.50 ml, 30.0 mmol) in MeOH (15 mL) was stirred for 2 d. After the removal of the solvent in vacuo, the residue was recrystallized from MeOH to give 4-tert-butylbenzohydrazide (1b) (2.94 g, 15.3 mmol, 57%) as a colorless crystal. 1 H-NMR (300 MHz, DMSO-d 6 ): delta 9.68 (s, 1H), 7.75 (d, J = 8.5 Hz, 2H), 7.45 (d, J = 8.5 Hz, 2H), 4.44 (s, 2H), 1.28 (s, 9H) ppm.

The synthetic route of 121-98-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Sakurai, Masayoshi; Kawakami, Rina; Kihara, Nobuhiro; Tetrahedron Letters; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 431-47-0, name is Methyl 2,2,2-trifluoroacetate, 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 431-47-0, Application In Synthesis of Methyl 2,2,2-trifluoroacetate

N-benzyl p-toluenesulfonamide (100 mg, 0.38 mmol), DMF (4 mL), potassium t-butoxide (129 mg, 1.15 mmol, 3 eq.) was added to the reaction flask in turn, and stirred at room temperature for 5 minutes. After the potassium tert-butoxide was uniformly dispersed, methyl trifluoroacetate (0.15 mL, 1.52 mmol, 4 eq.) was slowly injected into the reaction flask, and after 10 hours of reaction, stirring was stopped. It was extracted twice with ethyl acetate and distilled water, and then washed with a saturated NaCI solution. The magnesium sulfate was removed by filtration, and the solvent was evaporated. Purification by column chromatography to give N-methyl-N-benzyl-p-toluenesulfonamide (104 mg, yield 100%)

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; Guangdong Petrochemical College; Xiao Duoduo; Zheng Xin; Zeng Jiechun; Huang Jiawei; Zhou Rujin; Guan Ying; Liang Jieling; (8 pag.)CN109369506; (2019); A;,
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Related Products of 685-88-1, These common heterocyclic compound, 685-88-1, name is Diethyl fluoromalonate, 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 diethyl 2 fluoromalonate ester (1.0 g, 5.617 mmol) was added ethanol (10 ml), water (10ml), and lithium hydroxide monohydrate (0.943 g, 22.47mmol), then the reaction was stirred well for 16h at 50C. Then the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted in MTBE and water, then mixture was acidify with 6N HCl and then extracted with MTBE (5 x 50 ml). The combined organic layer were dried over Na2SO4, filtered and concentrated under reduced pressure to give 400 mg (yield 58%) of a white solid corresponding to 2-fluoromalonic acid. The crude product used in the next step without further purification. Synthesis of 2,4-dichloro-3-fluoroquinoline, intermediate 348-I-2

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

Reference:
Patent; GENOSCIENCE PHARMA; BRUN, Sonia; BERET, Antoine; BASSISSI, Firas; HALFON, Philippe; COURCAMBECK, Jerome; (275 pag.)WO2017/191599; (2017); A1;,
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Reference of 1559-02-0, 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 1559-02-0 as follows.

In the 2L three-mouth reaction bottle,Add 255.3 g of diethyl 1,1-cyclopropanedicarboxylate,840mL EtOH,The ice water bath cools it to 0 C.Slowly add 137.32g KHCO3The temperature control is added below 30 C.Naturally rise to room temperature,Stir the reaction for 15 h,TLC monitors the reaction completely,Add 1L of water,Extracted with (PE: EA = 1:1) 300 mL ¡Á 2,Remove the organic phase,Concentrated HCl adjusts pH=2,Extracted with EA 370mL¡Á2,Take the organic phase,Desolvent1,1-cyclopropanedicarboxylic acid monoethyl ester 201.7 g,The yield was 93%.

According to the analysis of related databases, 1559-02-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wuhan Institute of Technology; Huang Qimao; Feng Jinjin; Gao Hui; (13 pag.)CN105111155; (2018); B;,
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Adding a certain compound to certain chemical reactions, such as: 61644-18-6, name is Chloromethyl isobutyrate, 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 61644-18-6, HPLC of Formula: C5H9ClO2

A solution of compound Int-1 (100 mg, 0.239 mmol) in 1.2 mL of acetonitrile, was treated with potassium carbonate (99 mg, 0.717 mmol), potassium iodide (119 mg, 0.717 mmol), 18-crown-6 (3.16 mg, 0.012 mmol) followed by chloromethyl isobutyrate (65.3 mg, 0.478 mmol). The reaction mixture was stirred at 80C for 16 h. The resulting mixture was cooled to room temperature, and partitioned between ethyl acetate and water. The aqueous phase was back extracted with ethyl acetate and the combined organic layers were dried over Na2S04, filtrered, and concentrated in vacuo. The residue was purified on a XBridge1M C18, 30×250 mm column, eluting with acetonitrile / water (5 mM NH4HCO3) at 50 mL / min using a 20 min 20-90% acetonitrile / water gradient. Clean fractions were partitioned between water and (0266) dichloromethane. The organic phase was dried over Na2S04, filtered and concentrated to give compound 14. (0267) Compound 14: 1H MR (500 MHz, DMSO-i4) delta 10.30 (t, J= 5.9 Hz, 1H), 8.55 (s, 1H), 7.40 (td, J= 8.7, 6.6 Hz, 1H), 7.23 (td, J= 10.0, 2.6 Hz, 1H), 7.05 (td, J= 8.6, 2.5 Hz, 1H), 5.84 – 5.61 (m, 2H), 4.63 (dd, J= 14.4, 2.2 Hz, 1H), 4.58 – 4.46 (m, 3H), 3.89 (m, 1H), 3.87 – 3.76 (m, 1H), 3.44 (m, 1H), 2.45 (m, 1H), 2.23 (d, J= 10.2 Hz, 1H), 1.48 – 1.30 (m, 3H), 1.11 (s, 3H), 1.04 (d, J= 7.0 Hz, 6H). LCMS M+l = 519.3.

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; MERCK SHARP & DOHME CORP.; YU, Tao; MCCAULEY, John, A.; WHITEHEAD, Alan; APGAR, James, M.; RAHEEM, Izzat, T.; DONG, Guizhen; WADDELL, Sherman, T.; LI, Hong; (43 pag.)WO2018/140368; (2018); A1;,
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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, COA of Formula: C9H9ClO2

General procedure: Substituted aromatic acid (0.01 mol) was dissolved in 20 ml absolute ethanol added 1 ml conc. H2SO4 and refluxed for 8 h. The two third volume of reaction mixture was removed under reduced pressure and then poured into crushed ice and neutralized with sodium bicarbonate to obtain esters. In the subsequent step equimolar quantity of substituted ester (0.005 mol) and hydrazine hydrate (0.25 ml, 0.005 mol) in ethanol was refluxed for 24 h with stirring. The two third volume of alcohol was removed under reduced pressure and the reaction mixture was poured into the crushed ice. The resultant precipitate was filtered, washed with water and dried. The solid was recrystallized from 25 ml of 90 % ethanol. The purity of the compounds was checked by TLC using toluene-ethyl acetate-formic acid (5:4:1) as mobile phase.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4-chlorobenzoate, and friends who are interested can also refer to it.

Reference:
Article; Ahsan, Mohamed Jawed; Samy, Jeyabalan Govinda; Khalilullah, Habibullah; Nomani, Md. Shivli; Saraswat, Pankaj; Gaur, Ramakant; Singh, Abhimanyu; Bioorganic and Medicinal Chemistry Letters; vol. 21; 24; (2011); p. 7246 – 7250;,
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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. 10602-03-6, name is Ethyl 4-ethynylbenzoate, A new synthetic method of this compound is introduced below., Computed Properties of C11H10O2

General procedure: A solution of 4,5-dibromo-1,2-disubstituted-1H-imidazole 2, 7a-e, or 8a (1 mmol) or 5-alkynyl-4-bromo-1,2-dimethyl-1H-imidazole, alkyne 3 (3 mmol or 1.5 mmol), Pd(MeCN)2Cl2 (10 mg, 0.04 mmol, 4 mol%), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (26 mg, 0.04 mmol, 4 mol%), and CuI (3 mg, 0.02 mmol, 2 mol%) in DMF (4.5 mL) and DBU (0.5 mL) was stirred at 80 C for 3 h. The reaction mixture was then diluted with EtOAc (100 mL) and sat. aq NH4Cl (100 mL) was added. The resulting mixture was stirred in the open air for 0.5 h and then extracted with EtOAc. The combined organic extractswere washed with H2O (3 25 mL) and brine (25 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel. This procedure was employed to prepare 1,2-dimethylimidazole-fused enediynes 5a-e, 2-aryl-1-methylimidazole-fused enediynes 9a-d, and 1,2-diarylimidazole-fused enediyne 10a (Table 2).

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; Lessi, Marco; Panattoni, Alessandro; Guglielmero, Luca; Minei, Pierpaolo; Bellina, Fabio; Synthesis; vol. 51; 4; (2019); p. 933 – 943;,
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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. 14064-10-9, name is Diethyl 2-chloromalonate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 14064-10-9

A solution of the product of Example 107a (1.2 g, 4.4 mmol) and triethylamine (0.49 g, 4.8 mmol) in dichloromethane (25 ML) was treated dropwise with ethyl chloromalonate (0.73 g, 4.8 mmol), stirred for 2 hr and partitioned between ethyl acetate and water and the layers were separated.The ethyl acetate layer was washed with brine, dried (Na2SO4), and concentrated.The residue was purified by column chromatography on silica gel eluding with hexane and ethyl acetate (3:1) to provide the title compound (1.1 g, 65percent). MS (DCI) m/z 387 (M+H)+.

According to the analysis of related databases, 14064-10-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pratt, John K.; Betebenner, David A.; Donner, Pemela L.; Green, Brian E.; Kempf, Dale J.; McDaniel, Keith F.; Maring, Clarence J.; Stoll, Vincent S.; Zhang, Rong; US2004/87577; (2004); 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. 454-31-9, name is Ethyl 2,2-difluoroacetate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 2,2-difluoroacetate

Step 2 Preparation of 4,4-difluoro-1-(3-fluoro-4-methoxyphenyl)-butane-1,3-dione Ethyl difluoroacetate (4.06 g, 32.7 mmol) was dissolved in methyl t-butyl ether (50 mL). To the stirred solution was added 25 weight % sodium methoxide (7.07 g, 32.7 mmol) followed by 3′-fluoro-4′-methoxyacetophenone (5.0 g, 29.7 mmol). After stirring for 16 hours, 1N HCl (50 mL) was added. The organic layer was collected and washed with water (2*50 mL), dried over anhydrous MgSO4, filtered, and added to hexanes to precipitate a tan solid (7.0 g, 96%): mp 70-72 C.

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; Isakson; Peter C.; Anderson; Gary D.; Gregory; Susan A.; US5700816; (1997); A;,
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Electric Literature of 79383-44-1, 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. 79383-44-1, name is Methyl 2-methoxy-6-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows.

N-Bromosuccinimide (250mg) and catalytic amount of 2,2′-Azobis(2- methylpropionitrile) was added to a solution of 4 (252mg) in carbon tetrachloride (3.5mL). The reaction was heated to reflux in the present of visible light for 6h. After cooling to room

The chemical industry reduces the impact on the environment during synthesis Methyl 2-methoxy-6-methylbenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; ARANCIO, Ottavio; DENG, Shixian; LANDRY, Donald, W.; FIORITO, Jole; PURGATORIO, Rosa; WO2015/153410; (2015); A1;,
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