Tag: M.W=100-200

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. 28868-76-0, name is Dimethyl 2-chloromalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Dimethyl 2-chloromalonate

To 8.33 g of dimethyl chloromalonate, 10.7 ml of 7N ammonia/methanol solution was dropped at 0C and then stirred for 10 minutes. The reaction mixture was further stirred at room temperature for 2 hours, filtered and concentrated. The residue was dissolved with a mixed solvent of chloroform with methanol. The solution was filtered, and then concentrated. The residue was subjected to silica gel column chromatography to give 4.4 g of methyl 2-chloro-2-carboxamideacetate. Mp. 79.5C1H-NMR (300 M Hz, CDCl3, TMS delta (ppm) ) : 3.86 (s, 3H), 4.79 (s, 1H), 5.8-6.0 (bs, 1H), 6.5-6.7 (bs, 1H)

The synthetic route of 28868-76-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sumitomo Chemical Company, Limited; EP1422227; (2004); A1;,
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Reference of 50413-30-4, 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 50413-30-4 as follows.

To a stirred solution of compound If-I (7 g, 38.6 mmol) in pyridine (80 ml) was slowly added TsCI (8.8 g, 46.6 mmol) at rt. This solution was further stirred for 16h. The reaction mixture was poured into cold water upon which a solid was formed. The precipitate was filtered off and washed with n-pentane (50 ml) to afford the title compound If-2 as an off-white solid (10.8 g, 70% yield). LCMS [M+H] 336.

According to the analysis of related databases, 50413-30-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; MAMAI, Ahmed; (134 pag.)WO2019/119141; (2019); A1;,
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Electric Literature of 927-68-4, A common heterocyclic compound, 927-68-4, name is 2-Bromoethyl acetate, molecular formula is C4H7BrO2, 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.

EXAMPLE 50; 2-(Acetyloxy)ethyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-3-(2-thienyl)-1,6- dihydropyridazine-4-carboxylate; A mixture of the title product of Preparation 35 (0.15g, 0.42 mmol), potassium carbonate (0.17g, 12.63 mmol) and 2-bromoethylacetate (77.2 mg, 0.46 mmol) in dimethylformamide (4 ml) were heated at 50C for 4h. Once at room temperature, solvent was evaporated under reduced pressure and the residue was purified by flash chromatography (CH2CI2:MeOH 99: 1 as eluent). 0.13 g (68%) of the desired final product were isolated. m. p.: 161.0-161.6C No. (DMSO-d6): 1.4 (t, J=7.0 Hz, 3 H) 1.9 (s, 3 H) 2.2 (s, 2 H) 3.4 (m, 3 H) 3.9 (m, 2 H) 4.2 (q, J=7.0 Hz, 2 H) 7.0 (m, 2 H) 7.3 (d, J=5.0 Hz, 1 H) 7.6 (d, J=5.0 Hz, 1 H) 8.3 (s, 1 H) 8.3 (d, J=5.0 Hz, 1 H) 9.0 (s, 1 H)

The synthetic route of 927-68-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALMIRALL PRODESFARMA, S.A.; WO2005/123693; (2005); A1;,
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Reference of 37466-90-3, 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. 37466-90-3, name is Ethyl 3,4-diaminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step B: Preparation of 1H-benzo[d]imidazole-6-carboxylic acid ethyl ester 40 g of 3,4-diaminobenzoic acid ethyl ester (0.22 mol) and 200 mL formic acid were added to a three-necked bottle. After refluxing for 7 h, the reaction was completed. After concentration under reduced pressure, the ice water was poured into the residual solution. The resulting mixture was adjusted to pH 7 with sodium hydroxide. After sucking filtration, the filtrate was extracted with dichloromethane thrice, dried with anhydrous sodium sulfate, and decolored with active charcoal. Then the solution was concentrated under reduced pressure to get a white solid (29.6g). Yield: 70.2%. MS: 191 (M+1)

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, Ethyl 3,4-diaminobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenyang J & Health Pharmaceutical Co., Ltd.; EP2468730; (2012); A1;,
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3697-68-5, name is Ethyl 1-(hydroxymethyl)cyclopropanecarboxylate, 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. Formula: C7H12O3

REFERENCE EXAMPLE 1 Preparation of 2-bromomethylcyclopropanecarboxylic acid ethyl ester (2-formyl)cyclopropanecarboxylic acid ethyl ester (14.2 g, 0.10 mol) was dissolved in methanol (200 ml). The solution was cooled to 0 C., and sodium borohydride (3.8 g, 0.10 mol) was added. The mixture was stirred for 20 minutes. After distilling off the solvent, a saturated sodium chloride aqueous solution was added thereto. The product was extracted with chloroform, then dried and concentrated. Then, it was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain (2-hydroxymethyl)cyclopropanecarboxylic acid ethyl ester (14.3 g, yield: 99%). The (2-hydroxymethyl)cyclopropanecarboxylic acid ethyl ester (14.3 g, 0.1 mol) was dissolved in N,N-dimethylformamide (150 ml), and triphenylphosphine (25.9 g, 0.1 mol) was added thereto at room temperature. The mixture was stirred for 10 minutes. After cooling the mixture to 20 C., bromine (15.8 g, 0.1 mol) was dropwise added thereto over a period of 10 minutes. One hour later, the reaction mixture was added to a saturated sodium hydrogen carbonate solution, and the product was extracted with ethyl ether. It was dried, concentrated and then purified by column chromatography (hexane:ethyl acetate=5:1) to obtain (2-bromomethyl)cyclopropane carboxylic acid ethyl ester (15.3 g, yield: 74%). 1 NMR(CDCl3) delta0.9-1.0(m, 1H), 1.27(t, J=7.6 Hz, 3H), 1.3-1.5(m, 1H), 1.6-1.7(m, 1H, 1.8-2.0(m, 1H), 3.3-3.4(m, 2H), 4.25(q, J=7.6 Hz, 2H)

The synthetic route of 3697-68-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Asahi Glass Company, Ltd.; US5416231; (1995); A;,
Ester – Wikipedia,
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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. 2177-70-0, name is Phenyl methacrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: Phenyl methacrylate

Example 7 2.5 mL of tetrahydrofuran solution of 3.0 mol/L concentration of methylmagnesium chloride was added to 10 mL of anhydrous tetrahydrofuran in a reaction vessel under an atmosphere of argon, and then 1.0 g of 3,3,5-trimethylcyclohexanone was added with stirring while the mixture in the reaction vessel was kept at a temperature of 50 C. or less, followed by stirring for another one hour at the same temperature with stirring. Then, 1.20 g of phenyl methacrylate was added drop wise into the reaction vessel, and then 1.74 g of N,N,N’,N’-tetramethylethylene diamine, and the reaction was carried out with stirring for 24 hours at a temperature of 60 C. After the reaction, an aqueous saturated solution of ammonium chloride was added to the resulting reaction mixture, and the desired product was extracted with ethyl acetate. The obtained organic layer was subjected to gas chromatographic analysis. As a result, the yield of 1,3,3,5-tetramethylcyclohexyl methacrylate was found to be 18.0 mol %.

The synthetic route of 2177-70-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; HONSHU CHEMICAL INDUSTRY CO., LTD.; US2006/167305; (2006); A1;,
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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 35418-07-6 as follows. category: esters-buliding-blocks

General procedure: To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2 × 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white solid.

According to the analysis of related databases, 35418-07-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Jianyong; Li, Zheng; Li, Huilan; Liu, Chunxia; Wang, Nasi; Shi, Wei; Liao, Chen; Cai, Xingguang; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 8; (2017); p. 2445 – 2450;,
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These common heterocyclic compound, 122-72-5, name is 3-Phenylpropyl Acetate, 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: C11H14O2

General procedure: A general procedure for the manganese-catalysed benzylic amination is as follows. A Teflon stir bar and 5 A powdered molecular sieves (40 mg) were added in a 10 ml round-bottom flask, which was sealed with a Suba Seal rubber septum, placed under vacuum, flame-dried for 45 s to activate the molecular sieves, cooled under a purged and completely air-free argon balloon and wrapped in foil to exclude light. Once cooled, solvent (0.40 ml, 0.5 M to substrate) and substrate (0.20 mmol, 1 equiv.) were added and stirred for 10 min. Manganese(iii) perchlorophthalocyaninechloride 3 (23.1 mg, 0.020 mmol, 0.1 equiv.) and silver hexafluoroantimonate (6.9 mg, 0.020 mmol, 0.1 equiv.) were weighed in a foil-wrapped 1-dram vial in the glove box and sealed with a Teflon cap. The vial was removed from the glove box and the contents added directly to the round-bottom flask while maintaining an argon atmosphere, then stirred for 10 min at room temperature. In a 1-dram vial open to air, 2,2,2-trichloroethyl (phenyl-lambda 3-iodanylidene)sulfamate (172.2 mg,0.40 mmol, 2 equiv.) was weighed and added directly to the round-bottom flask while maintaining an argon atmosphere. The Suba Seal rubber septum was replaced by a polyethylene cap, sealed tightly, and placed in a 40 C oil bath for 8 h with stirring. Upon reaction completion, the reaction was filtered through a 1 inch silicagel plug using diethyl ether or ethyl acetate as the eluent. The crude material was concentrated and dry-loaded directly onto a silica gel column.

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

Reference:
Article; Clark, Joseph R.; Feng, Kaibo; Sookezian, Anasheh; White, M. Christina; Nature Chemistry; vol. 10; 6; (2018); p. 583 – 591;,
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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. 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, A new synthetic method of this compound is introduced below., Computed Properties of C7H14ClNO3

To available thiophen-3-ylamine 2p1 (0.50 g, 5.04 rnmol) was added imidate2g2 (1.08g, 5.5mmol) in ethanol (10 mL) under a N2 atmosphere. The mixture wasstirred at R.T. for 3 h at which point the reaction was concentrated. To the residuewas added ether, and the suspension filtered and washed with ether to afford adduct2p2(1.0g, 82percent). This material was sufficiently clean to be used in the subsequentstep. MS: 242.1 (MH)+.

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; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; BOEHRINGER INGELHEIM PHARMA GmbH & CO KG; WO2006/85; (2006); A1;,
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Application of 455-75-4, A common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, molecular formula is C9H10FNO2, 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.

Intermediate 33: N-{5-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide; Step A: Ethyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-4-fluorobenzoate; To a solution of ethyl 3-amino-4-fluorobenzoate (5.47 g, 30 mmol) and pyridine (2.55 mL, 33 mmol) in DCM (150 mL) was added 2,6-difluorobenzenesulfonyl chloride (4.45 mL, 33 mmol). The reaction was stirred overnight at rt. After 16 h, the reaction mixture was concentrated, triturated with ether, and dried in vacuo to generate 7.87 g (66% yield) of the product of Step A as a white powder. MS (ESI): 360 (M+H).

The synthetic route of 455-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
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