Category: 67442-07-3

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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, A new synthetic method of this compound is introduced below., Computed Properties of C4H8ClNO2

A solution of 2.5 M n-butyl lithium in hexanes (35ml, 87.6mmol) was added to a solution of the bromide from preparation 29 (20.0g, 79.7mmol) in ferf-butyl methylether (300ml) at -78¡ãC under nitrogen over 10 minutes. The reaction was stirred for a further 10 minutes and 2-chloro-N-methoxy-N-methyl-acetamide (12.1g, 87.6mmol) in terf-butyl-methylether (40ml) was added slowly. The reaction was stirred at -78¡ãC for 20 minutes and then 1M hydrochloric acid (200ml) was added. The mixture was allowed to warm to room temperature, stirred for 2 hours and the organic phase separated. The aqueous phase was extracted with fe/f-butyl methylether and the combined organic extracts were washed with water (100ml), saturated aqueous sodium chloride (100ml) and 1M sodium hydroxide (100ml). The organic phase was dried (sodium sulfate), concentrated in vacua and the residual oil purified by flash column chromatography on silica gel eluting with pentane:dichloromethane:methanol (75:25:0 changing to 0:99:1, by volume). The residue was recrystallised from pentane:dichloromethane to give the title compound as a yellow solid.1H NMR (400MHz, CDCI3): 5 = 9.11 (1H, s), 8.34-8.33 (1H, d), 7.32-7.30 (1H,d), 5.91 (2H, s), 4.66 (2H, s), 2.17 (6H, s) ppm.LRMS (electrospray): m/z [M-H]+ 247.

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; PFIZER LIMITED; PFIZER INC.; WO2004/108676; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 67442-07-3, 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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows.

iPrMgCl*LiCl (Turbo Grignard, 1.3 mol/L in tetrahydrofuran, 25.6 mL) is added dropwise to a flask charged with a stir bar, 2-iodo-5-bromo-pyridine (9.00 g), and tetrahydrofuran (180 mL) and chilled to -30¡ã C. The mixture is stirred in the cooling bath for 1 h. 2-Chloro-N-methoxy-N-methylacetamide (4.58 g) dissolved in tetrahydrofuran (20 mL) is added dropwise over 5 min. The mixture is stirred for 30 min and then quenched by the addition of aqueous 1 M HCl solution. The mixture is concentrated, and the aqueous residue is extracted with ethyl acetate. The combined extract is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 20:1?1:1) to give the title compound. Mass spectrum (ESI+): m/z=234/236/238 (Br+Cl) [M+H]+.

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

Reference:
Patent; Boehringer Ingelheim International GmbH; ECKHARDT, Matthias; WAGNER, Holger; PETERS, Stefan; (43 pag.)US2018/148411; (2018); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Application of 67442-07-3, A common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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.

Under nitrogen protection, 1340.5g of intermediate was taken, dissolved in 200mL anhydrous THF, the reaction system was cooled to -15¡ã, and 13g of THF solution of 13g isopropylmagnesium chloride was added dropwise. During the dropwise addition, the reaction temperature was controlled at -5¡ã. After the completion of the dropwise addition, the reaction was continued for 1 h, and then 60 g of a solution of 15 g of 2-chloro-N-methoxy-N-methylacetamide in THF was added dropwise thereto, and the reaction temperature was controlled not to exceed -5¡ã during the dropwise addition. After the end of the addition, the temperature of the system was raised to -5-0 ¡ã, and after the reaction was completed, the reaction was quenched by the addition of 2N hydrochloric acid at 0 ¡ã, and ethyl acetate (200 mL) was added, and the mixture was separated. , filtration, solvent recovery under reduced pressure, residue,With methanol:Water = 10:1 recrystallized to give a white solid, 27 g, yield 76percent.

The synthetic route of 67442-07-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu Engineering Polytechnic College; Feng Chengliang; Yao Wenjin; Yan Bin; (12 pag.)CN109678686; (2019); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, molecular formula is C4H8ClNO2, 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. 67442-07-3

To an oven dried, N2-flushed 100 mL round bottom flask was added 5-cyclohexyl-5-methylimidazolidine-2,4-dione (Example 2.47d) (6.77 g, 32.9 mmol), K2CO3 (6.80 g, 49.3 mmol) 32 mL of anhydrous DMF and commercially available 2-chloro-N-methoxy-N-methylacetamide (4.74 g, 34.5 mmol). The reaction was stirred at 50¡ã C. for 12 h. The reaction was cooled and 70 mL water was added with stirring. The precipitate was filtered and dried to afford 8.9 g (92percent) of 2-(4-cyclohexyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-N-methoxy-N-methylacetamide as a white solid. (0741) To an oven dried, N2-flushed 100 mL round bottom flask was added 2-(4-cyclohexyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-N-methoxy-N-methylacetamide (8.90 g, 29.9 mmol), Cs2CO3 (13.65 g, 41.9 mmol), 30 mL DMF and methyl iodide (2 mL, 31.4 mmol). The reaction was stirred for 24 hours and 60 mL water was added. The mixture was extracted with ether (3¡Á50 mL). The combined organic layers were washed with water (1¡Á100 mL), brine and dried with Na2SO4. The solvent was evaporated, and the residue was purified by column chromatography utilizing a Silicycle column (120 g) and elution with 20-70percent ethyl acetate/hexane to afford 8.2 g (88percent) of the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) delta 4.28 (s, 2H), 3.73 (s, 3H), 3.10 (s, 3H), 2.78 (s 3H), 1.79-1.49 (m, 6H), 1.39-1.25 (m, 4H), 1.23-0.82 (m, 4H); MS 312 (MH+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 67442-07-3, its application will become more common.

Reference:
Patent; SENOMYX, INC.; Chumakova, Lyudmyla; Patron, Andrew; Priest, Chad; Karanewsky, Donald; Kimmich, Rachel; Boren, Brant Clayton; Hammaker, Jeffrey Robert; Chumakov, Volodymyr; Zhao, Wen; Noncovich, Alain; Ung, Jane; (146 pag.)US2015/376136; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, A new synthetic method of this compound is introduced below., 67442-07-3

Benzylmagnesium chloride (1.0 M in diethyl ether, 50.0 mL) was treated with 2-chloro-N-methoxy-N-methylacetamide (5.16 g, 37.5 mmol) in tetrahydrofuran (200 mL) at -78¡ã C. drop wise. The reaction was allowed to warm slowly to room temperature overnight and quenched with 1N hydrochloric acid. The layers were separated and the organic phase dried (Na2SO4), filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel; elution with hexanes) to provide the title. 1H NMR (300 MHz, DMSO-d6) delta 3.87 (s, 2H), 4.62 (s, 2H), 7.25 (m, 5H); MS (DCI/NH3) m/z 186 (M+NH4)+.

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; Kolasa, Teodzyj; Patel, Meena; Mortell, Kathleen H.; Matulenko, Mark A.; Hakeem, Ahmed A.; Bhatia, Pramila A.; Wang, Xueqing; Daanen, Jerome F.; Latshaw, Steven P.; Stewart, Andrew O.; US2005/176727; (2005); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

These common heterocyclic compound, 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, 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. 67442-07-3

To a solution of bromo pyridine from example 38 (2g, 8. 0mmol) at-78¡ãC, in dry THF (30ml), was added butyllithium (2.5M in hexanes) (3. 5ml 8. 8MMOL), dropwise over 20 minutes. The reaction mixture was stirred for 30 minutes +, HEN 2-chloro-N-methoxy-N-methylacetamide (1.2g, 8. 8MMOL) in dry THF (20ml) was added dropwise keeping the temperature AT-78¡ãC. Stirring was continued for 30 minutes at this temperature before 1 M HCI (aq) (50ml) was added and the reaction mixture warmed to room temperature. The organic layer was separated and the aqueous layer washed with ethyl acetate (56ml). The organic layers were combined then washed with 3M NAOH (aq) (1 OML) and brine (20ml) before being dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give crude title compound as a brown oil (1.34g, 5. 4mmol, 67percent). 1H NMR (CDCI3, 400MHZ) 6 : 2.20 (s, 6H), 4.68 (s, 2H), 5.92 (s, 2H), 7.32 (d, 1 H), 8.38 (d, 1 H), 9.16 (s, 1 H). LRMS: m/z 249 (M-H+).

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 67442-07-3.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.; WO2004/52372; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 67442-07-3 as follows. 67442-07-3

1. 2-Imidazol-1-yl-N-methoxy-N-methyl-acetamide 60percent sodium hydride in oil (0.296 g, 7.4 mol) was washed with tetrahydrofuran and suspended in additional tetrahydrofuran (10 ml). To this was added imidazole (0.506 g, 7.43 mol) followed by stirring at 25¡ã C. for 1 hour. To the mixture was added a solution of 2-chloro-N-methoxy-N-methyl-acetamide (1.02 g, 7.4 mmol, prepared per Tetrahedron Letters Vol. 30, No. 29, pp3779-80, 1989.) followed by stirring at 25¡ã C. for 15. The mixture was filtered, and the filtrate was evaporated to an oil in vacuo and purifide by chromatography on silica gel eluted with a gradient of chloroform to 10percent methanol:chloroform giving a solid 0.46 g, 37percent yield.

According to the analysis of related databases, 67442-07-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Denny, William Alexander; Hutchings, Richard H; Johnson, Douglas S; Kaltenbronn, James Stanely; Lee, Ho Huat; Leonard, Daniele Marie; Milbank, Jared Bruce John; Repine, Joseph Thomas; Rewcastle, Gordon William; White, Andrew David; US2004/44057; (2004); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 67442-07-3 name is 2-Chloro-N-methoxy-N-methylacetamide, 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. 67442-07-3

4-Iodo-1-(4-methoxybenzyl)-1H-pyrazole (8.1 g, 26 mmol) was dissolved in THF (50 mL) and cooled in an ice bath. Isopropylmagnesium chloride (2.9 M, 8.9 mL, 26 mmol) was added slowly. The reaction mixture was stirred for 10 minutes, and then 2- chloro-N-methoxy-N-methylacetamide (3.5 g, 26 mmol) dissolved in THF (15 mL) was added slowly by syringe. The reaction mixture was warmed to ambient temperature and stirred for 1 hour. The reaction mixture was partitioned between EtOAc and iN HC1, and the organic layer was dried over sodium sulfate, filtered and concentrated to afford crude 2-chloro-1-(l-(4- methoxybenzyl)- 1 H-pyrazol-4-yl)ethanone (7.1 g, 27 mmol, 104 percent yield) as an amber oil that slowly solidified.

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

Reference:
Patent; ARRAY BIOPHARMA INC.; CELGENE CORPORATION; ALLEN, Shelley; BOYS, Mark Laurence; CHICARELLI, Mark J.; FELL, Jay Bradford; FISCHER, John P.; GAUDINO, John; HICKEN, Erik James; HINKLIN, Ronald Jay; KRASER, Christopher F.; LAIRD, Ellen; ROBINSON, John E.; TANG, Tony P.; BURGESS, Laurence E.; RIEGER, Robert Andrew; PHENEGER, Jed; SATOH, Yoshitaka; LEFTHERIS, Katerina; RAHEJA, Raj K.; BENNETT, Brydon L.; (223 pag.)WO2016/90285; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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. 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, This compound has unique chemical properties. The synthetic route is as follows., 67442-07-3

(d) To a solution of 0.33 g (0.83 mmol) 3-acetoxy-4-fluoro-N-[4-(imidazol-1-yl)-3-trifluoromethylphenyl]-benzamide, J-1c, in 5 mL acetone and 0.5 mL of methanol was added cesium carbonate (0.54 g, 1.65 mmol) and 2-chloro-N-methoxy-N-methyl-acetamide (0.15 g, 1.07 mmol) and the resulting mixture was stirred for 6 h at 45¡ã C. After cooling to room temperature, the mixture was partitioned between ethyl acetate and sat. brine (2*20 mL). The organic layer was filtered though a silica gel plug and concentrated. The residue was purified by titurated with diethyl ether (2*20 mL) to give 0.35 g (92percent) of 4-fluoro-N-[4-(imidazol-1-yl)-3-trifluoromethylphenyl]-3-[(N-methoxy-N-methylcarbamoyl)methoxy]benzamide, J-1d, as a white solid: Rt=11.95 min.; 1H NMR (300 MHz, CDCl3) delta8.34 (d, 1H, J=2.4 Hz), 8.11 (dd, lh, J=8.7 Hz), 7.64-7.54 (m, 3H), 7.42 (d, 1H, J=8.7 Hz), 7.22-7.15 (m, 2H), 6.97 (s, 1H), 502 (s, 2H), 3.72 (s, 3H), 3.06 (s, 3H); MS (ESI): Calculated for C21H18F4N4O4 (M+H+): 467, Found: 467.

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; Bender, Steven Lee; Bhumralkar, Dilip; Collins, Michael Raymond; Cripps, Stephen James; Deal, Judith Gail; Jia, Lei; Nambu, Mitchell David; Palmer, Cynthia Louise; Peng, Zhengwei; Varney, Michael David; US2002/103203; (2002); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 67442-07-3, name is 2-Chloro-N-methoxy-N-methylacetamide, 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 67442-07-3. 67442-07-3

into the reactor add LD-I and tetrahydrofuran; Replace nitrogen 3 times, under nitrogen protection, cool the solution at-12 C, slowly add 2N iso-propylmagnesium chloride THF solution, the resulting reaction solution is stirred at -12C for 1h, until the reaction is complete, dissolve 2-chloro-N-methoxyl-N-methylacetamide into methyl tert-butyl ether, after that slowly add 2-chloro-N-methoxyl-N-methylacetamide solution into the reactor, while dropping, keep the internal temperature at -10C, adjust the internal temperature at 0C and continue stirring for 2 hours, after the reaction is completed, 1N hydrochloric acid is added and the layers are separated, and extracting the aqueous layer with methyl tert-butyl ether, combining organic layers, concentrate under reduced pressure at 10 volumes, adjust the temperature at 20 C, and stir for 1.5h, centrifuge, and wash the filter cake with isopropyl alcohol, dried, and obtained solid product LD-J.

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 2-Chloro-N-methoxy-N-methylacetamide.

Reference:
Patent; Anhui Nuoquan Pharmaceutical Co., Ltd.; Du Xiaopeng; Xu Liangzhi; Hu Zhigang; He Darong; Qian Zhujin; He Yong; Liu Zhuangzi; (12 pag.)CN107879908; (2018); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics