Method for synthesizing 2-(N-4-methyl benzyl) methoxy-acetamido methyl isobutyrate

A technology of methyl methoxyacetamido isobutyrate and methyl benzylidene aminoacetate, applied in the field of synthesis of 2-(N-4-methylbenzyl) methyl methoxyacetamido isobutyrate, Achieve the effect of reducing air pollution, low cost and convenient operation

Inactive Publication Date: 2012-09-12
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Methyl 2-(N-4-methylbenzyl)methoxyacetamidoisobutyrate is a new compound, so far there is no report about this compound

Method used

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  • Method for synthesizing 2-(N-4-methyl benzyl) methoxy-acetamido methyl isobutyrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] a. Preparation of electrolyte

[0018] Mix 0.001 mol (0.191g) methyl p-methylbenzylidene aminoacetate with 0.001 mol (0.369g) tetra-n-butylammonium iodide and 0.129 mol (10 mL) N,N-dimethylformamide to form an electrolyte , and then placed in a one-chamber electrolytic cell with stainless steel as the cathode and magnesium rod as the anode, methyl p-methylbenzylidene aminoacetate, tetra-n-butylammonium iodide and N,N-dimethylformamide as analytically pure , wherein: methyl p-methylbenzylidene aminoacetate is the substrate, N,N-dimethylformamide is the solvent after drying with 4? grade molecular sieves, and tetra-n-butylammonium iodide is the supporting electrolyte.

[0019] b. Electrocarboxylation reaction

[0020] Under normal pressure, carbon dioxide is introduced into the electrolytic cell to saturation, and then at 2.9mA / cm 2 The constant current electric carboxylation reaction is carried out at a current density of 96.5°C and the reaction temperature is 25°C.

...

Embodiment 2

[0026] a. Preparation of electrolyte

[0027] Mix 0.001 mol (0.191g) methyl p-methylbenzylidene aminoacetate with 0.001 mol (0.369g) tetra-n-butylammonium iodide and 0.129 mol (10 mL) N,N-dimethylformamide to form an electrolyte , and then placed in a one-chamber electrolytic cell with stainless steel as the cathode and magnesium rod as the anode, methyl p-methylbenzylidene aminoacetate, tetra-n-butylammonium iodide and N,N-dimethylformamide as analytically pure , wherein: methyl p-methylbenzylidene aminoacetate is the substrate, N,N-dimethylformamide is the solvent after drying with 4? grade molecular sieves, and tetra-n-butylammonium iodide is the supporting electrolyte.

[0028] b. Electrocarboxylation reaction

[0029] Under normal pressure, carbon dioxide is introduced into the electrolytic cell to saturation, and then at 2.9mA / cm 2 The constant current electric carboxylation reaction is carried out at a current density of 193°C, and the reaction temperature is 25°C.

...

Embodiment 3

[0035] a. Preparation of electrolyte

[0036] Mix 0.001 mol (0.191g) methyl p-methylbenzylidene aminoacetate with 0.001 mol (0.369g) tetra-n-butylammonium iodide and 0.129 mol (10 mL) N,N-dimethylformamide to form an electrolyte , and then placed in a one-chamber electrolytic cell with stainless steel as the cathode and magnesium rod as the anode, methyl p-methylbenzylidene aminoacetate, tetra-n-butylammonium iodide and N,N-dimethylformamide as analytically pure , wherein: methyl p-methylbenzylidene aminoacetate is the substrate, N,N-dimethylformamide is the solvent after drying with 4? grade molecular sieves, and tetra-n-butylammonium iodide is the supporting electrolyte.

[0037] b. Electrocarboxylation reaction

[0038] Under normal pressure, carbon dioxide is passed into the electrolytic cell to saturation, and then at 3.5mA / cm 2 The constant current electric carboxylation reaction is carried out at a current density of 386°C, and the reaction temperature is 22°C.

[00...

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Abstract

The invention discloses a method for synthesizing 2-(N-4-methyl benzyl) methoxy-acetamido methyl isobutyrate. The method is characterized by comprising the following steps of: mixing p-methyl iminobenzyl methyl acetate, N,N-dimethylformamide and tetrabutylammonium iodide, saturating carbon dioxide under normal pressure, performing electrical carboxylation reaction under the condition of constant current, esterifying and purifying to obtain the 2-(N-4-methyl benzyl) methoxy-acetamido methyl isobutyrate. Compared with the prior art, the method has the advantages of simple process, convenience for operation, safety and readily available raw materials; and the carbon dioxide serving as greenhouse effect gas is utilized effectively, atmospheric pollution is reduced greatly, and the conversion of aromatic imine compounds and the effective synthesis of N-carboxylation products are realized simultaneously, so the method is a process route with industrial synthetic value.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a method for synthesizing methyl 2-(N-4-methylbenzyl)methoxyacetamido isobutyrate. Background technique [0002] In recent years, various organic compounds centered on the activation and fixation of carbon dioxide by electrochemical methods, including electrocarboxylation reactions containing activated groups such as C-X, C=C, and C=O, have attracted more and more attention. However, regarding C= However, there are few reports on the electrocarboxylation of N. The imine compound containing C=N unsaturated double bond has poor stability and is easy to decompose when encountering water and acid, so the electrocarboxylation reaction of this compound is generally difficult to carry out. Weinberg et al. reported in Weinberg, N. L.; Hoffmann, A. K.; Reddy, T. B. Tetrahedron Lett, 1971, 25, 2271 in the electrocarboxylation of benzylidene aniline in molten tetraethyla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/00C07C271/22C07C269/00
Inventor 王欢李瑞娜何丽徐晓明赵学如吴靓陆嘉星
Owner EAST CHINA NORMAL UNIV
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