Category: 6919-61-5

Adding a certain compound to certain chemical reactions, such as: 6919-61-5, name is N-Methoxy-N-methylbenzamide, belongs to amides-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 6919-61-5, HPLC of Formula: C9H11NO2

N-Methoxy-N-methyl benzamide 20 (0.1 g, 0.60 mmol) was dissolved in anhydrous diethyl ether (2.01 ml). The solution was cooled to 0 C. To this, vinyl magnesium bromide solution (0.91 ml, 1.0 M in THF) was added dropwise over 30 min at 0 C. After the completion of addition, the reaction mixture was stirred for a further 60 min at 0 C and for 30 min at room temperature. It was then quenched with 1M HCl at 0 C. The reaction mixture was diluted with diethyl ether. The organic layer was washed with brine, dried over Na2SO4,concentrated in vacuo, purified on silica gel (3:1 hexanes/EtOAc) to afford 0.04 g of 7 (55%) as a colorless oil. 1H NMR (400 MHz, CDCl3) ae 7.95 (d, J = 8.3 Hz, 2H), 7.60-7.55 (m, J = 7.4 Hz,1H), 7.49 (t, J = 8.0 Hz, 2H), 7.15 (dd, J = 10.5 Hz, 6.6 Hz, 1H), 6.40 (d, J = 17.1 Hz, 1H), 5.90(d, J = 10.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) ae 191.2, 137.5, 133.1, 132.6, 130.2, 128.8,128.7. HRMS C9H9O [M+H]+ Expected: 133.0648, Found: 133.0646.

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, N-Methoxy-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Korwar, Sudha; Nguyen, Thuy; Ellis, Keith C.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 271 – 274;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 6919-61-5, A common heterocyclic compound, 6919-61-5, name is N-Methoxy-N-methylbenzamide, molecular formula is C9H11NO2, 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 a solution of 5.0g (25.4 mmol) of tetaut-butyldimethyl-pent-4-ynylochiy-silane (prepared by the method of Koseki, Y.; Sato, H.; Watanabe, Y.; Nagasaka, T. Org. Lett. 2002, 4, 885-888) in 10OmL of THF at -78C under an atmosphere of N2 was added dropwise 10.2 mL (25.4 mmol) of 2.5 M nBuLi in hexane. After stirring for Ih at that temperature, 4.0 g (24.2 mmol) of N-methoxy-N-methyl benzamide (2-1) in 20 mL of THF was added, the cooling bath was removed, and stirring was continued for 3h at room temperature. The reaction was quenched with saturated aqueous NH4Cl, extracted with 2 x EtOAc, washed with brine, dried over Na2SO4, and concentrated. The crude material was loaded onto a 4Og silica gel cartridge and eluted with a gradient of 0 to 55% EtOAc in hexanes over 25 minutes to provide 6.3g (20.9 mmol, 87%) of the propargylic ketone (2-2) as a pale yellow oil. To a suspension of 2.2g (10.7 mmol) of CuBrOMS in 30 mL of THF at -78C was added 10.7 mL (21.4 mmol) of a 2.0 M solution of PhLi in dibutylether. After stirring for 1.5h, 2.7g (8.9 mmol) of the above prepared ketone 2-2 in 5mL of THF was added, and the mixture was allowed to stir for an additional 3h at -78C, and warmed to 00C for 15 minutes before being quenched with saturated aqueous NH4Cl. The mixture was partitioned with EtOAc, the layers were separated, the aqueous was extracted with 2 x EtOAc, the organics were combined, washed with brine, dried over Na2SO4, and concentrated. The crude material was loaded onto a 4Og silica gel cartridge and eluted with a gradient of 0 to 25% EtOAc in hexanes to provide 2.89g (7.6 mmol, 85%) of 2-3 as a yellow oil; NMR analysis indicated that there was a 1.1:1 mixture of E:Z isomers. Careful separation of a fraction of this material provided the pure isomers, whose identities were determined by ID NOE analysis. Data for 2-3-(E) (first to elute): 1HNMR (500 MHz, CDCl3) delta 8.0 (m, 2H), 7.6 – 7.4 (m, 8H), 7.1 (s, IH), 3.7 (t, J = 6.3 Hz, 2H), 3.1 (m, 2H), 1.75 (m, 2H), 0.9 (s, 9H), 0.01 (s, 6H) ppm. Data for 2-3-(Z) (second to elute): 1HNMR (500 MHz, CDCl3) delta 7.8 (m, 2H) 7.45 (m, IH), 7.35 (m, 2H), 7.25 – 7.1 (m, 5H), 6.7 (s, IH), 3.65 (t, J = 6.3 Hz, 2H), 2.65 (t, J = 7.6 Hz, 2H), 1.7 (m, 2H), 0.9 (s, 9H), 0.05 (s, 6H) ppm. Data for mixture 2-3: HRMS (ES) calc’d M + H for C24H32O2Si: 381.2245. Found: 381.2251

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; MERCK & CO., INC.; WO2006/7501; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Electric Literature of 6919-61-5, A common heterocyclic compound, 6919-61-5, name is N-Methoxy-N-methylbenzamide, molecular formula is C9H11NO2, 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 a solution of 5.0g (25.4 mmol) of tetaut-butyldimethyl-pent-4-ynylochiy-silane (prepared by the method of Koseki, Y.; Sato, H.; Watanabe, Y.; Nagasaka, T. Org. Lett. 2002, 4, 885-888) in 10OmL of THF at -78C under an atmosphere of N2 was added dropwise 10.2 mL (25.4 mmol) of 2.5 M nBuLi in hexane. After stirring for Ih at that temperature, 4.0 g (24.2 mmol) of N-methoxy-N-methyl benzamide (2-1) in 20 mL of THF was added, the cooling bath was removed, and stirring was continued for 3h at room temperature. The reaction was quenched with saturated aqueous NH4Cl, extracted with 2 x EtOAc, washed with brine, dried over Na2SO4, and concentrated. The crude material was loaded onto a 4Og silica gel cartridge and eluted with a gradient of 0 to 55% EtOAc in hexanes over 25 minutes to provide 6.3g (20.9 mmol, 87%) of the propargylic ketone (2-2) as a pale yellow oil. To a suspension of 2.2g (10.7 mmol) of CuBrOMS in 30 mL of THF at -78C was added 10.7 mL (21.4 mmol) of a 2.0 M solution of PhLi in dibutylether. After stirring for 1.5h, 2.7g (8.9 mmol) of the above prepared ketone 2-2 in 5mL of THF was added, and the mixture was allowed to stir for an additional 3h at -78C, and warmed to 00C for 15 minutes before being quenched with saturated aqueous NH4Cl. The mixture was partitioned with EtOAc, the layers were separated, the aqueous was extracted with 2 x EtOAc, the organics were combined, washed with brine, dried over Na2SO4, and concentrated. The crude material was loaded onto a 4Og silica gel cartridge and eluted with a gradient of 0 to 25% EtOAc in hexanes to provide 2.89g (7.6 mmol, 85%) of 2-3 as a yellow oil; NMR analysis indicated that there was a 1.1:1 mixture of E:Z isomers. Careful separation of a fraction of this material provided the pure isomers, whose identities were determined by ID NOE analysis. Data for 2-3-(E) (first to elute): 1HNMR (500 MHz, CDCl3) delta 8.0 (m, 2H), 7.6 – 7.4 (m, 8H), 7.1 (s, IH), 3.7 (t, J = 6.3 Hz, 2H), 3.1 (m, 2H), 1.75 (m, 2H), 0.9 (s, 9H), 0.01 (s, 6H) ppm. Data for 2-3-(Z) (second to elute): 1HNMR (500 MHz, CDCl3) delta 7.8 (m, 2H) 7.45 (m, IH), 7.35 (m, 2H), 7.25 – 7.1 (m, 5H), 6.7 (s, IH), 3.65 (t, J = 6.3 Hz, 2H), 2.65 (t, J = 7.6 Hz, 2H), 1.7 (m, 2H), 0.9 (s, 9H), 0.05 (s, 6H) ppm. Data for mixture 2-3: HRMS (ES) calc’d M + H for C24H32O2Si: 381.2245. Found: 381.2251

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; MERCK & CO., INC.; WO2006/7501; (2006); A2;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 6919-61-5, name is N-Methoxy-N-methylbenzamide, belongs to amides-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 6919-61-5, name: N-Methoxy-N-methylbenzamide

N-Methoxy-N-methyl benzamide 20 (0.1 g, 0.60 mmol) was dissolved in anhydrous diethyl ether (2.01 ml). The solution was cooled to 0 C. To this, vinyl magnesium bromide solution (0.91 ml, 1.0 M in THF) was added dropwise over 30 min at 0 C. After the completion of addition, the reaction mixture was stirred for a further 60 min at 0 C and for 30 min at room temperature. It was then quenched with 1M HCl at 0 C. The reaction mixture was diluted with diethyl ether. The organic layer was washed with brine, dried over Na2SO4,concentrated in vacuo, purified on silica gel (3:1 hexanes/EtOAc) to afford 0.04 g of 7 (55%) as a colorless oil. 1H NMR (400 MHz, CDCl3) ae 7.95 (d, J = 8.3 Hz, 2H), 7.60-7.55 (m, J = 7.4 Hz,1H), 7.49 (t, J = 8.0 Hz, 2H), 7.15 (dd, J = 10.5 Hz, 6.6 Hz, 1H), 6.40 (d, J = 17.1 Hz, 1H), 5.90(d, J = 10.6 Hz, 1H); 13C NMR (100 MHz, CDCl3) ae 191.2, 137.5, 133.1, 132.6, 130.2, 128.8,128.7. HRMS C9H9O [M+H]+ Expected: 133.0648, Found: 133.0646.

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, N-Methoxy-N-methylbenzamide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Korwar, Sudha; Nguyen, Thuy; Ellis, Keith C.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 1; (2014); p. 271 – 274;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics