Category: 122334-37-6

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. 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, A new synthetic method of this compound is introduced below., Application In Synthesis of 4-Chloro-N-methoxy-N-methylbenzamide

Ethylmagnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a period of several minutes in an ice bath under nitrogen atmosphere to a solution of 5-bromo-1-methyl-1H-imidazole G, 64.4 mmol). A white precipitate was formed upon addition. The mixture was removed from the ice bath, stirred for 20 min and then cooled again in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, intermediate 1: step a) . The resulting white suspension was stirred at room temperature overnight. The reaction was quenched by the addition of a saturated aqueous NH4Cl solution and diluted with water. The mixture was partially concentrated, the THF was removed and diluted with DCM. The mixture was acidified to pH 1 with 1 N HCl aqueous solution and then neutralized with saturated aqueous NaHCO3 solution. The phases were separated and the aqueous phase further extracted with DCM. The organic extracts were washed with water, then dried (Na2SO4), filtered and concentrated to give a white solid. The crude product was triturated with a mixture of EtOAc: heptane (1: 1, 150 mL). The precipitated solid was collected by vacuum filtration and washed with heptane to give the title compound.

The synthetic route of 122334-37-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica, N.V; Leonardo, Christie.A; Barubay, Kent; Edward, James P.; Kirsten, Kevin D.; Kumar, David A.; Maharupe, Uma; Nishimura, Rachel; Urbanski, Modu; Venkatesan, Hariharan; Wang, Ai Hua; OhLynn, Ronald L.; Woods, Craig R.; Fourier, Anne; Shu, Jia Hu; Cummings, Maxwell D.; (50 pag.)KR2016/70823; (2016); A;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Some common heterocyclic compound, 122334-37-6, name is 4-Chloro-N-methoxy-N-methylbenzamide, molecular formula is C9H10ClNO2, 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. category: amides-buliding-blocks

Ethyl magnesium bromide (3.0 M in diethyl ether, 21.5 mL, 64.4 mmol) was added via syringe over a few minutes to a clear colorless solution of 5-bromo-1-methyl-1H-imidazole (10.4 g, 64.4 mmol) in THF (100 mL) under a nitrogen atmosphere in an ice bath. A white precipitate formed during the addition. The mixture was removed from the ice bath and was stirred for 20 minutes, then was again cooled in an ice bath before addition of 4-chloro-N-methoxy-N-methylbenzamide (10.7 g, 53.6 mmol, Intermediate 22: step a). The resulting white suspension was stirred overnight at room temperature. The reaction was quenched by addition of saturated aqueous NH4Cl and diluted with water. The mixture was partially concentrated to remove THF and was diluted with DCM. The mixture was acidified to pH 1 with 1 N aqueous HCl, then neutralized with saturated aqueous NaHCO3. The phases were separated and the aqueous phase was further extracted with DCM. The organic extracts were washed with water, then were dried (Na2SO4), filtered, and concentrated, affording a white solid. The crude product was triturated with a mixture of EtOAc:heptanes (1:1, 150 mL). The precipitated solid was collected by vacuum filtration, washing with heptanes, to afford the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 122334-37-6, its application will become more common.

Reference:
Patent; JOHNSON & JOHNSON; LEONARD, KRISTI A.; BARBAY, KENT; EDWARDS, JAMES P.; KREUTTER, KEVIN D.; KUMMER, DAVID A.; MAHAROOF, UMAR; NISHIMURA, RACHEL; URBANSKI, MAUD; VENKATESAN, HARIHARAN; WANG, AIHUA; WOLIN, RONALD L.; WOODS, CRAIG R.; FOURIE, ANNE; XUE, XIAOHUA; CUMMINGS, MAXWELL D.; MCCLURE, KELLY; TANIS, VIRGINIA; US2015/111870; (2015); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics