Category: 6283-71-2

Reference of 6283-71-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 6283-71-2 name is Dimethyl 2-cyanosuccinate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of dimethyl 2-cyanobutanedioate (CAS 6283-71-2, 10.0 g, 58.4 mmol, 1.00 eq) in methanol (60.0 niL) and water (60.0 mL) was added triethylamine (8.87 g, 87.6 mmol, 12.1 mL, 1 50 eq) at 0- 5 C. After stirring for 30 minutes, ten- butyl prop-2-enoate (CAS 1663-39-4, 8.99 g, 70.1 mmol, 10.2 mL, 1.20 eq) was added to the reaction mixture. The mixture was stirred at 0- 5 C for 1.5 hours and was allowed to warm to 25 C and stirred for a further 2 hours TLC showed that starting material was consumed and one new spot was detected. The reaction mixture was acidified with 2 N aq HC1 to pH = 4 and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (50 mL), dried over NaiSCX filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography (SiC , petrol ether: ethyl acetate = 20: 1 to 4: 1) to afford 4-0-tert-butyl 1-6), 2-O-dimethyl 2-cyanobutane- 1,2, 4- tricarboxylate (10.0 g, 33.4 mmol, 57.2%) as a yellow gum. NMR: 400 MHz, CDCh: d 3.82- 3 87 (m, 3H), 3.73 (s, 3H), 3.09 (d, ./ 17.07 Hz, 11 1 ), 2.83 id, J = 17 32 Hz, i l l), 2 47- 2 61 ( n, (1198) 1H), 2.31- 2.43 (m, 1H), 2.10- 2.25 (m, 2H), 2.03 (s, 1H), 1.43 (s, 9H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dimethyl 2-cyanosuccinate, and friends who are interested can also refer to it.

Reference:
Patent; C4 THERAPEUTICS, INC.; NASVESCHUK, Christopher, G.; DEY, Fabian; GOERGLER, Annick; KUHN, Bernd; NORCROSS, Roger; ROEVER, Stephan; SCHMID, Philipp; (270 pag.)WO2019/204354; (2019); 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. 6283-71-2, name is Dimethyl 2-cyanosuccinate, A new synthetic method of this compound is introduced below., Product Details of 6283-71-2

To a solution of dimethyl 2-cyanobutanedioate (compound 62a, 513 mg, 3 mmol) in acetone (5 mL) was added iodomethane (639 mg, 4.5 mmol) and potassium carbonate (829 mg, 6 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with EtOAc twice, washed with water. The combined organic phase was dried over Na2SO4, filtrated and concentrated to give compound 62b (556 mg, crude). LCMS (M+H+): 186.

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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HU, Taishan; KOU, Buyu; LIN, Xianfeng; LIU, Haixia; ZHANG, Zhisen; (152 pag.)WO2018/11160; (2018); A1;,
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Reference of 6283-71-2, 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. 6283-71-2, name is Dimethyl 2-cyanosuccinate, This compound has unique chemical properties. The synthetic route is as follows.

Cyanodiester 12 (1.16 g; 6.78 mmol) was dissolved in ethanol/water 1:1 (12 mL), cooled to 0-5 C and Et3N (1.2 mL) was added dropwise. After 15 min tert-butyl acrylate (1.05 mL; 0.92 g; 7.14 mmol) was added dropwise. The mixture was stirred at 0-5 C for 1.5 h, allowed to warm to room temperature and stirred for further 2 h. It was then concentrated, diluted with water, acidified with 2 N HCl to pH 4 and extracted 3* with AcOEt. The combined organic extracts were dried with MgSO4, concentrated in vacuo and chromatographed on silica gel in hexane/AcOEt (4:1) to give 20 (0.61 g; 29%; Rf 0.27) and 21 (0.77 g; 38%; Rf 0.23) as colourless oils.

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

Reference:
Article; Weinberg, Kamil; Stoit, Axel; Kruse, Chris G.; Haddow, Mairi F.; Gallagher, Timothy; Tetrahedron; vol. 69; 23; (2013); p. 4694 – 4707;,
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Electric Literature of 6283-71-2, These common heterocyclic compound, 6283-71-2, name is Dimethyl 2-cyanosuccinate, 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.

Sodium nitrite (1.32 g, 19.1 mmol) was added carefully to sulphuric acid (concentrated, 6.8 ml), whilst cooling the solution to 0° C. The solution was heated to 60° C. for 30 min, allowed to cool and then diluted with acetic acid (12 ml). To the solution was added Preparation 182 (5.0 mg, 17.4 mmol) in acetic acid (11 ml) and the reaction mixture was heated at 55° C. for 1 h. To a solution of Preparation 248 (3.09 g, 18.1 mmol) in acetic acid (24 ml) and water (36 ml) was added dropwise the solution of the diazonium salt, followed by sodium acetate (24.2 g) in water (42 ml). The reaction mixture was then stirred at room temperature for 30 min. The reaction mixture was poured into ice/water (200 ml) and the mixture was extracted with dichloromethane (4.x.60 ml). The combined extracts were then washed with ammonium hydroxide (48 ml), dried and concentrated in vacuo. To a solution of sodium methoxide (25 wt.percent, 11.5 ml, 50.1 mmol) in methanol (450 ml) was added dropwise a solution of the residue in methanol (100 ml). The reaction mixture was then stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and to the residue was added water. This solution was adjusted to pH 1 by addition of hydrochloric acid (4 N) and the mixture was extracted with dichloromethane (3.x.100 ml). The combined extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography, eluting with hexane/ethyl acetate [3: 1]. The appropriate fractions were combined and concentrated to give the titled compound (4.5 g). Experimental MH+ 379.8; expected 380.0

The synthetic route of 6283-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Billen, Denis; Boyle, Jessica; Critcher, Douglas James; Gethin, David Morris; Hall, Kim Thomas; Kyne, Graham Michael; US2006/287365; (2006); A1;,
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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. 6283-71-2, name is Dimethyl 2-cyanosuccinate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: Dimethyl 2-cyanosuccinate

Preparation 100; 1- [2, 6-dichloro-4-pentafluorothiophenyl]-5-hydroxy-1 H-pyrazole-3-carbonitrile; Sodium nitrite (1.32 g, 19.1 mmol) was added carefully to sulphuric acid (concentrated, 6.8 ml), whilst cooling the solution to 0°C. The solution was heated to 60°C for 30 min, allowed to cool and then diluted with acetic acid (12 ml). To the solution was added 2, 6-dichloro-4-pentafluorothiophenylamine (WO 9421606 A1, 5.0 mg, 17.4 mmol) in acetic acid (11 ml) and the reaction mixture was heated at 55°C for 1 h. To a solution of dimethyl 2-cyanosuccinate (Hall, H. K. , Jr.; Ykman, P. , J. Am. Chem. Soc. (1975), 97 (4), 800-807,3. 09 g, 18.1 mmol) in acetic acid (24 mi) and water (36 ml) was added dropwise the solution of the diazonium salt, followed by sodium acetate (24.2 g) in water (42 ml). The reaction mixture was then stirred at room temperature for 30 min. The reaction mixture was poured into ice/water (200 ml) and the mixture was extracted with dichloromethane (4 x 60 ml). The combined extracts were then washed with ammonium hydroxide (48 ml), dried and concentrated in vacuo. To a solution of sodium methoxide (25 wt. percent, 11.5 ml, 50.1 mmol) in methanol (450 ml) was added dropwise a solution of the residue in methanol (100 ml). The reaction mixture was then stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and to the residue was added water. This solution was adjusted to pH 1 by addition of hydrochloric acid (4N) and the mixture was extracted with dichloromethane (3 x 100 ml). The combined extracts were dried (MgS04) and concentrated in vacuo. The residue was purified by column chromatography, eluting with hexane/ethyl acetate [3: 1]. The appropriate fractions were combined and concentrated to give the titled compound (4. 5g). Experimental MH+ 379.8 ; expected 380.0

The synthetic route of 6283-71-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2005/90313; (2005); A1;,
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