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Synthesis process of furoxan-3,4-diethyl phthalate

A technology of diethyl dicarboxylate and furoxan oxide is applied in the direction of organic chemistry, etc., which can solve the problems of difficulty in obtaining raw materials, dangerous experimental operation, and high cost of raw materials, and achieve the effects of reducing the generation of waste acid, reducing costs, and simplifying processes

Active Publication Date: 2016-08-24
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
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Problems solved by technology

The synthetic method of oxyfurazan-3,4-dicarboxylate mainly contains following several kinds: the one is with the sodium salt of methyl dinitroacetate as raw material, N 2 o 4 Synthesized as an oxidizing agent, but the raw material cost of this method is high, and the experimental operation is more dangerous; the second is to use diethyl 2-nitromalonate as a raw material, which is oxidized and synthesized into a ring, and the yield is 70%, but the raw material is difficult to obtain
The third is to use monoethyl malonate potassium salt as a raw material, and use nitric acid / sodium nitrite as an oxidant to obtain diethyl oxyfurazan-3,4-dicarboxylate through oxidative nitration and ring-forming reaction, but the raw material is expensive and difficult obtain; the fourth is to use ethyl nitroacetate as a raw material, and copper acetate or concentrated sulfuric acid is used as an oxidant to synthesize, but the cost of raw materials is high, and the reaction 15h yield is only 43% when copper acetate is used as an oxidant; the fifth is to use ethyl acetoacetate as Raw material, after sodium nitrite and dilute HNO 3 It is obtained by nitrosation and oxidation to form a ring, but the yield and purity of diethyl oxyfurazan-3,4-dicarboxylate prepared by this method are low
Sixth, ethyl chlorooximyloacetate is used as raw material and synthesized by oxidation with a yield of 70%, but the raw material is difficult to obtain

Method used

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  • Synthesis process of furoxan-3,4-diethyl phthalate

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Experimental program
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Embodiment 1

[0020] 0.196g concentrated H 2 SO 4 Add to 50 mL of acetic anhydride. After the mixture is cooled to -10°C, 12.7 mL of HNO with a mass fraction of 95% is added dropwise while stirring 3 , Control temperature 10~15℃. The reaction mixture was cooled to -5°C, 26.028g ethyl acetoacetate was added dropwise, and the temperature was maintained at -5°C during the addition, and the reaction was maintained for 1h after the addition was completed. The temperature was raised to 20°C, and 3.20 mL of concentrated sulfuric acid was added dropwise to the reaction solution, followed by TLC until the reaction was complete (1.1h). The mixture was extracted three times with ethyl acetate, washed with saturated brine, and the extracts were combined and anhydrous Na 2 SO 4 Dry and filter. The ethyl acetate was evaporated by rotary evaporation, the residue was distilled under reduced pressure, and the fractions were collected. The obtained diethyl furazan-3,4-dicarboxylate is a pale yellow liquid w...

Embodiment 2

[0022] 0.600 g of trifluoromethanesulfonic acid was added to 50 mL of acetic anhydride. After the mixture is cooled to -5°C, 12.7 mL of HNO with a mass fraction of 95% is added dropwise while stirring 3 , Control temperature 10~15℃. The reaction mixture was cooled to -5°C, 26.028g ethyl acetoacetate was added dropwise, and the temperature was maintained at -5°C during the addition, and the reaction was maintained for 1h after the addition was completed. The temperature was raised to 20°C, and 3.20 mL of concentrated sulfuric acid was added dropwise to the reaction solution, followed by TLC until the reaction was complete (1.1h). The mixture was extracted three times with ethyl acetate, washed with saturated brine, and the extracts were combined and anhydrous Na 2 SO 4 Dry and filter. The ethyl acetate was evaporated by rotary evaporation, the residue was distilled under reduced pressure, and the fractions were collected. The obtained diethyl furazan-3,4-dicarboxylate is a pal...

Embodiment 3

[0024] 0.384 g methanesulfonic acid was added to 50 mL acetic anhydride. After the mixture is cooled to -5°C, 12.7 mL of HNO with a mass fraction of 95% is added dropwise while stirring 3 , Control temperature 10~15℃. The reaction mixture was cooled to -5°C, 26.028g ethyl acetoacetate was added dropwise, and the temperature was maintained at -5°C during the addition, and the reaction was maintained for 1h after the addition was completed. The temperature was raised to 20°C, and 3.20 mL of concentrated sulfuric acid was added dropwise to the reaction solution, followed by TLC until the reaction was complete (1.1h). The mixture was extracted three times with ethyl acetate, washed with saturated brine, and the extracts were combined and anhydrous Na 2 SO 4 Dry and filter. The ethyl acetate was evaporated by rotary evaporation, the residue was distilled under reduced pressure, and the fractions were collected. The obtained diethyl furazan-3,4-dicarboxylate is a pale yellow liquid...

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Abstract

The invention relates to a synthesis process of furoxan-3,4-diethyl phthalate. With ethyl acetoacetate as the raw material, furoxan-3,4-diethyl phthalate is synthesized through nitration and oxidative cyclization; the yield is 81.4%, the purity is higher than 98%, and nuclear magnetic characterization and infrared characterization is performed on the product. The process has the advantages that raw materials are easy to obtain, the process is simple, and the yield and the purity are high.

Description

Technical field [0001] The invention relates to the field of organic chemistry, in particular to the one-pot synthesis of diethyl oxyfurazan-3,4-dicarboxylate. Background technique [0002] Oxyfurazan-3,4-dicarboxylate is an important raw material for the synthesis of furazan-4-amino-3-acyl azide (ANFO), which contains two highly reactive groups, namely primary amino and acyl Azide is a key intermediate for the synthesis of furoxan compounds. The synthesis methods of oxyfurazan-3,4-diethyl dicarboxylate mainly include the following: One is the sodium salt of methyl dinitroacetate as the raw material, N 2 O 4 It is synthesized as an oxidant, but the method has high raw material cost and relatively dangerous experimental operation. Second, it uses diethyl 2-nitromalonate as the raw material and oxidizes it into a ring synthesis. The yield is 70%, but the raw material is difficult to obtain. Third, the potassium salt of monoethyl malonate is used as the raw material, and nitric aci...

Claims

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Application Information

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IPC IPC(8): C07D271/08
Inventor 李斌栋王敏
Owner NANJING UNIV OF SCI & TECH
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