Novel process for preparing acetamino diethyl malonate

A technology of diethyl acetamidomalonate and diethyl nitrosomalonate, which is applied in the field of preparing diethyl acetamidomalonate, which can solve the problems of difficult handling, high production cost, and low yield of products, etc. problem, to achieve the effect of increasing product yield, reducing production cost and simplifying process steps

Inactive Publication Date: 2006-12-13
安徽省恒锐新技术开发有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] After searching, the existing synthesis process and method using diethyl malonate as raw material generally have disadvantages such as high consumption of raw and au

Method used

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  • Novel process for preparing acetamino diethyl malonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of step 1 diethyl nitrosomalonate

[0019] Add 130ml of diethyl malonate (0.8mol), 35g (0.8mol) of sodium nitrite, 6ml of water and 190ml of toluene into a 1000ml three-necked flask, and dropwise add 80ml of glacial acetic acid below 5°C. After the dropwise addition, slowly raise the temperature to 40-50°C, react for 6 hours, then add water to dissolve the unreacted salt, pour it into a separatory funnel, wash the organic layer with 5% NaCl aqueous solution, discard the aqueous layer, evaporate The toluene solvent from the organic layer was 145.2 g of light yellow oily liquid, with a purity of 98.5% and a yield of 96.0% (calculated as diethyl malonate).

[0020] Step 2 Preparation of Diethyl Acetylaminomalonate

[0021] Take the above 76g of diethyl nitrosomalonate (0.4mol), 60g of acetic anhydride (0.6mol), and 36g of glacial acetic acid (0.6mol), mix well, slowly add 65g of zinc powder, and control the feeding temperature at 40-50°C . After the addition...

Embodiment 2

[0023] Preparation of step 1 diethyl nitrosomalonate

[0024] Same as step 1 of example 1

[0025] Step 2 Preparation of Diethyl Acetylaminomalonate

[0026] Take 76g of diethyl nitrosomalonate (0.4mol), 60g of acetic anhydride (0.6mol), 36g (0.6mol) of glacial acetic acid, mix well, add 2g of Rany Ni catalyst, replace the reaction system with nitrogen and hydrogen successively Air, flow hydrogen, stir and heat, control the temperature at 60-70°C, control the hydrogen pressure at 1.2MPa, react for 2-3 hours, stop the flow of hydrogen, filter while hot, and wash the filter cake twice with 40g hot acetic acid. The combined filtrates were distilled under reduced pressure to recover acetic acid. When crystals are precipitated, stop the distillation, add 100ml of distilled water to heat and dissolve, then cool in an ice-water bath and stir vigorously, let it stand for 2 hours to filter, wash the filter cake with cold distilled water, dry, and recover the mother liquor to obtain a...

Embodiment 3

[0028] Preparation of step 1 diethyl nitrosomalonate

[0029] Same as step 1 of example 1

[0030] Step 2 Preparation of Diethyl Acetylaminomalonate

[0031] Take the above 76g of diethyl nitrosomalonate (0.4mol), 81.6g of acetic anhydride (0.8mol), 36g of glacial acetic acid (0.6mol), mix well, slowly add 65g of zinc powder, and the temperature of the addition is controlled at 40-50 ℃. After the addition, react at 50-60°C for 1 hour, filter while hot, and wash the filter cake twice with 40 g of hot acetic acid. The combined filtrates were distilled under reduced pressure to recover acetic acid. When crystals are precipitated, stop the distillation, add 100ml of distilled water to heat and dissolve, then cool in an ice-water bath and stir vigorously, let it stand for 2 hours to filter, wash the filter cake with cold distilled water, dry, and recover the mother liquor to obtain a white powder 80.5 g of crystals, the melting point is 96.0-98.5°C, and the total yield of reduc...

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Abstract

The invention relates the new technology of preparing acylated amino-compound, especially preparing acetamino-diethyl malonate with diethyl malonate. The method comprises the following steps: using diethyl malonate and sodium nitrite as raw material to prepare nitroso- diethyl malonate, mixing nitroso- diethyl malonate, acylating agent and solvent at the ratio of 1:1-2:1-2, adding reducer, stirring, after acylating, filtering to remove fouled catalyst, filter liquor carrying out vacuum distillation to recover acetic acid, when a great amount of crystals separate out, cooling, filtering, drying and getting product. The productivity of acetamino-diethyl malonate is above 95%. The technology is fit for mass production.

Description

technical field [0001] The invention relates to a new process for preparing amido compounds, in particular to a new process for preparing acetamidodiethyl malonate by using diethyl malonate as a raw material. Background technique [0002] Diethyl acetamidomalonate is an important raw material and intermediate in organic synthesis and pharmaceutical synthesis, especially in the synthesis of unnatural amino acids. With the development of the amino acid and peptide industry, the demand is increasing year by year, but due to technical limitations, the production of this product has not been able to meet the demand, and the demand gap in my country alone has reached nearly 1,000 tons. [0003] The synthetic route of diethyl acetamidomalonate that has been developed at home and abroad includes the synthetic route with chloroacetic acid and sodium cyanide as raw materials and the synthetic route with diethyl malonate as the main raw material. The former has been eliminated due to ...

Claims

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Application Information

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IPC IPC(8): C07C233/47C07C231/02
Inventor 柴多里马云峰王组元吴梅
Owner 安徽省恒锐新技术开发有限责任公司
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