Tag: M.W=100-200

Reference of 443-26-5, 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. 443-26-5, name is Ethyl 2-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5,6-Dihydro-cyclopenta[b]thiophen-4-one (2.1 g, 15.0 mmol) in 15 mL of THF was treated with NaH (60 percent, 1.5 g, 36 mmol). After the addition of 3-Fluoro-benzoic acid ethyl ester, the reaction mixture was heated at 100 C. for 8 hr. The solution was cooled to room temperature and poured into water. The resulting mixture was acidified with concentrated HCl and was added with ethyl acetate (70 mL). The organic layer was collected, brined, dried over MgSO4(s), and concentrated under reduced pressure. The resultant precipitate was collected and recrystallized from ethanol to provide the corresponding 5-(2-Fluoro-benzoyl)-5,6-dihydro-cyclopenta[b]thiophen-4-one (0.56 g, 2.1 mmol) as brown solid in 14% yield.

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 2-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DEVELOPMENT CENTER FOR BIOTECHNOLOGY; LIAO, Chu-Bin; CHIANG, Chao-Cheng; YANG, Huei-Ru; LIAO, Yuan-Chun; CHEN, Paonien; US2013/274255; (2013); 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 141-12-8 as follows. Product Details of 141-12-8

6.983g (0.035mol) of 1a was added to a stirring solution of 0.491g (3.5mmol) of salicylic acid, 0.665g (3.5mmol) of SeO2 and 14.82g (0.164mol) of tert-butylhydroperoxide (70%) in 35mL of diethyl ether at 0C and left to stir for 48h. The volume of the mixture was then reduced to one half and was washed with 15mL of 5% NaHCO3, saturated CuSO4, repeatedly washed with saturated Na2S2O3, water, brine and then dried over MgSO4. Solvent was removed by rotary evaporation and the crude oil was then purified by flash chromatography (5% EtOAc/hexanes) to afford 3.53g (47%) of 2a. TLC: (Rf 0.7). 1H NMR (300MHz): delta 9.28 (s, 1H), 6.37 (t, 1H), 5.32 (t, 1H), 4.49 (d, 2H), 2.39 (q, 2H), 2.25 (t, 2H), 1.91 (s, 3H) 1.69 (s, 3H), 1.58 (s, 3H). 13C NMR (76MHz): delta 195.2, 171.0, 153.2, 140.8, 139.7, 120.5, 60.7, 30.4, 27.3, 25.8 (contaminant), 23.2, 21.0, 9.2.

According to the analysis of related databases, 141-12-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Mostafavi, Anahita Z.; Lujan, Donovan K.; Erickson, Katelyn M.; Martinez, Christina D.; Troutman, Jerry M.; Bioorganic and Medicinal Chemistry; vol. 21; 17; (2013); p. 5428 – 5435;,
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Related Products of 21961-31-9, These common heterocyclic compound, 21961-31-9, name is Methyl 3-amino-5-chlorobenzoate, 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.

3-Amino-5-chloro-benzoic acid methyl ester (CAS 21961-31-9, 0.400 g) was dissolved in 10.5 ml of chloroform and treated at 0 C with 0.344 g of isobutyryl chloride (1.5 eq.) and 0.90 ml of triethylamine. After stirring for 2 h at ambient temperature, the reaction mixture was poured onto crashed ice/HCl-solution, extracted twice with AcOEt, washed with water, dried over sodium sulfate, and evaporated i. V. Flash chromatography (Si02, hexane/AcOEt=7/3) yielded finally 0.546 g of pure 3-chloro-5-isobutyrylamino-benzoic acid methyl ester as white waxy solid. MS 256.0 ([M+H]+). It was dissolved in 12.8 ml of THF/EtOH =1/1, treated with 6.4 ml (3 eq.) of IN NaOH and kept at ambient temperature for 2 h. The reaction mixture was then poured onto crashed ice/AcOEt/HCl dil., the aqueous phase extracted again with AcOEt, the combined organic layers were washed with water, dried over sodium sulfate, and evaporated to dryness to produce 0.529 g of 3-chloro-5-isobutyrylamino-benzoic acid as white solid. MS 240.1 ([M-H]”).

Statistics shows that Methyl 3-amino-5-chlorobenzoate is playing an increasingly important role. we look forward to future research findings about 21961-31-9.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2006/27135; (2006); 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. 145576-28-9, name is Ethyl 4-methylenecyclohexanecarboxylate, A new synthetic method of this compound is introduced below., COA of Formula: C10H16O2

At 0 C, to a solution of ethyl 4-methylenecyclohexanecarboxylate (0.08 g) in DCE (1 mL) was added chloroiodomethane (0.110 mL, 1.522 mmol), followed bythe addition of 1 N diethylzinc in hexane (0.76 1 mL, 0.76 1 mmol). The reaction was stirred at 0 C for 1 hr, then stirred at rt for 18 hrs. The reaction mixture was diluted with EtOAc and 1 N HC1, the organic phase was washed with sat. NaC1, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was charged to a 25 g silica gel cartridge which was eluted with a 20 mm gradient of 0-6% EtOAc inhexane to yield ethyl spiro[2.5]octane-6-carboxylate. ?H NMR (400 MHz, CDC13) ppm 4.08-4.18(2 H, m), 2.32 (1 H, tq, J=11.01, 3.53 Hz), 1.85 – 1.93 (2 H, m), 1.53- 1.74 (4 H, m), 1.28 – 1.35 (2 H, m), 1.22 – 1.28 (3 H, m), 0.28 (2 H, ddd, J=8.53, 5.52, 1.51 Hz), 0.17 – 0.25 (2 H, m).

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; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
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Some common heterocyclic compound, 5164-76-1, name is Dimethyl pent-2-enedioate, molecular formula is C7H10O4, 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. Application In Synthesis of Dimethyl pent-2-enedioate

General procedure: The crude aryl diazonium tosylate 9 thus obtained was dissolved or suspended in MeOH (30 mL). Dimethyl glutaconate (1.45 mL, 10.0 mmol) and Pd(OAc)2 (112 mg, 0.5 mmol) were successively added while stirring. After stirring at r.t. for 15 h, the mixture was concentrated under reduced pressure and partitioned between CH2Cl2 (40 mL) and H2O (25 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. The residue was briefly fractionated on SiO2 using CH2Cl2 or CH2Cl2- acetone (5:1) as eluent. Fractions containing arylation product were pooled and concentrated to give compound 10 of at least 90% purity (according to 1H NMR analysis). It was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5164-76-1, its application will become more common.

Reference:
Article; Dar’In, Dmitry; Kantin, Grigory; Bakulina, Olga; ?alubovskis, Raivis; Krasavin, Mikhail; Synthesis; vol. 51; 10; (2019); p. 2230 – 2236;,
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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. 185629-32-7, name is Methyl 4-amino-3-fluorobenzoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8FNO2

To a 1L round-bottom flask was added methyl 4-amino-3-fluorobenzoate 30a (20 g, 118.24 mmol, 1.0 equiv.), AcOH (400 mL), and NaSCN (38.34 g, 473.33 mmol, 4.0 equiv.). The mixture was cooled at 0 C, and bromine (18.7 g, 117.01 mmol, 1.0 equiv) was added dropwise with stirring. The reaction mixture was stirred at 0 C for 2 hours, then at 30C for 3 days. 400 mL of water was added, the pH value of the solution was adjusted to 9 using sodium hydroxide. Solids were collected by filtration and dried in an oven under reduced pressure, to give 28 g (crude) of methyl 2-amino-4-fluoro-l,3-benzothiazole-6-carboxylate 30b as a yellow solid. The crude product was carried onto the next step without further purification.

According to the analysis of related databases, 185629-32-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; (231 pag.)WO2019/55808; (2019); A1;,
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Reference of 609-08-5, 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. 609-08-5, name is Diethyl 2-methylmalonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 6 Preparation of Diethyl 2-fluoro-2-methylmalonate Diethyl 2-methylmalonate (870 mg, 860 muL, 5 mmole) was dissolved in anhydrous tetrahydrofuran (10 mL) under nitrogen. Sodium hydride (250 mg as a 60% oil dispersion, 6 mmole) was added and the mixture was stirred until hydrogen evolution ceased (about 15 minutes). The reaction mixture was diluted with toluene (20 mL) and transferred dropwise to a solution of N-fluoro-N-neopentyl-p-toluenesulfonamide (1.295 g, 5 mmole) in anhydrous toluene (10 mL) over 5 minutes. A precipitate formed during addition and the reaction temperature rose from 23 to 36. After stirring an additional 5 minutes under nitrogen, the reaction mixture was diluted with ether (100 mL), washed with aqueous 1N oxalic acid (30 mL), 10% aqueous potassium bicarbonate (30 mL), and saturated aqueous sodium chloride (30 mL) solutions, and then dried over anhydrous magnesium sulfate. Filtration, removal of solvent under reduced pressure, and purification by flash column chromatography (silica, 1:1 methylene chloride-hexane) yielded diethyl 2-fluoro-2-methylmalonate (512 mg, 53% yield) as a colorless liquid. This material, and additional samples prepared by this procedure, were analyzed and provided the following results: IR (liquid film) gammamax (cm-1) 2940 (m), 1750 (s, ester), 1440 (m), 1370 (m), 1290 (s); 1 H NMR (80 MHz, CDCl3) delta1.33 (t, J=8 Hz, 6H, CH2 CHHD 3), 1.81 (d, J=22.67 Hz, 3H, CH3), 4.30 (q, J=8 Hz, 4H, CH2); 19 F NMR (94.1 MHz, CDCl3) -158.02 (q, J=22 Hz, 1F); HRMS (M–CH2 CH3) calcd. for C6 H8 O3 F: 147.0457; found: 147.0450; LRMS (CI) m/e 193.

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

Reference:
Patent; E. I. Du Pont de Nemours and Company; US4479901; (1984); A;,
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Adding a certain compound to certain chemical reactions, such as: 18469-52-8, name is Methyl 4-(aminomethyl)benzoate, 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 18469-52-8, SDS of cas: 18469-52-8

(1) To a solution of methyl 4-(aminomethyl)benzoate (5.08 g) in methylene chloride (30 mL) was added di-tert-butyl dicarbonate (6.4 g) under ice-cooling and the mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted with methylene chloride (20 mL) and thereto was added water (40 mL). After stirring, the organic layer was separated and concentrated in vacuo to give crude methyl 4-[N-(tert-butoxycarbonyl)aminomethyl] benzoate.

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; TANABE SEIYAKU CO., LTD.; EP1772454; (2007); 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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, A new synthetic method of this compound is introduced below., Recommanded Product: Ethyl 2-ethoxy-2-iminoacetate

A mixture of 2-chloropyridine-3-sulfonamide (115) (50 mg, 0.26 mmol), ethyl 2-ethoxy-2- iminoacetate (56 mg, 0.39 mmol) and DBU (79 mg, 0.52 mmol) in ethanol (5 mL) was heated in a sealed tube at 130 C for 0.5 h then cooled to r.t.. The mixture was diluted with water (5 mL), adjusted to pH 5 with 1 M aqueous HCI and extracted with DCM (10 mL x 3). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by preparative TLC (MeOH/DCM = 1 :20) to give the product as a yellow solid (10 mg, 15% yield). LCMS (ES-API) Rt 0.51 min; m/z 256.1 [M+H]+. 1H NMR (400 MHz, d6-DMSO) 8.81 (dd, J = 4.8, 2.0 Hz, 1H), 8.43 (dd, J = 8.0, 1.6 Hz, 1H), 7.63 (dd, J = 8.0, 4.8 Hz, 1H), 4.41 (q, J = 7.2 Hz, 2H), 1.37 (t, J = 7.2 Hz, 3H).

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; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
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Electric Literature of 46193-76-4,Some common heterocyclic compound, 46193-76-4, name is Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, molecular formula is C9H9NO2S, 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) Preparation of thiophene pyrrole:Lipidothiophene pyrrole (1.95 g, 10 mmol)And potassium hydroxide (1 g, 18 mmol)Mixed in ethylene glycol (19.5 mL)Under inert gas protection and dark conditions, heated to 150 reaction 3h,After cooling to room temperature, add a large amount of distilled water to dilute,Extract with chloroform several times,Organic phase with water,Saturated sodium chloride solution,After drying, the solvent was removed by rotary evaporation,Quickly purified by silica gel column,Dichloromethane as eluent,Point before collecting components, dried to give thiophene pyrrole,Yield 85%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate, its application will become more common.

Reference:
Patent; Henan Normal University; Chang Yi; Niu Mengyuan; Liu Mengyang; (11 pag.)CN106905351; (2017); A;,
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