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Synthesis method of nitrocyclopropane

A technology of nitrocyclopropane and nitropropane, which is applied in the field of synthesis of pharmaceutical and pesticide intermediates, and can solve the problems of low yield and no application prospect

Inactive Publication Date: 2018-04-20
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has a low yield and has no application prospect

Method used

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  • Synthesis method of nitrocyclopropane
  • Synthesis method of nitrocyclopropane

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Experimental program
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Embodiment 1

[0015] At 0°C, 30 mL of dichloromethane, 3 g (0.075 mol) of sodium hydroxide and 0.05 g (2.2×10 -4 mol) benzyltriethylammonium chloride, and then 10.8 grams (0.05mol) of 1-iodo-3-nitropropane was added dropwise. After the dropwise addition, the temperature was raised, refluxed for 0.5 hours, and cooled to room temperature. The reaction solution was washed twice with water and separated. The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness to obtain 5.2 g of a light yellow transparent liquid. It was confirmed to be nitrocyclopropane by NMR analysis, with a yield of 92.6% and a purity of 95.2%.

[0016] 1 H NMR (CDCl 3 ,500MHz,δ / ppm):4.25(m,1H),1.64(m,2H),1.15(m,2H).

Embodiment 2

[0018] At 0°C, 30 mL of ethyl acetate, 4 g (0.1 mol) of sodium hydroxide and 0.11 g (5×10 -4 mol) benzyltriethylammonium chloride, and then 8.4 grams (0.05mol) of 1-bromo-3-nitropropane were added dropwise. After the dropwise addition, the temperature was raised to 60° C. to react for 1 hour, and then cooled to room temperature. The reaction solution was washed twice with water and separated. The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness to obtain 5 g of a light yellow transparent liquid. It was confirmed to be nitrocyclopropane by NMR analysis, with a yield of 88.2% and a purity of 94%.

Embodiment 3

[0020] At 0°C, 30 mL of toluene, 4 g (0.1 mol) of sodium hydroxide and 0.05 g (2.2×10 - 4 mol) benzyltriethylammonium chloride, and then 6.2 grams (0.05mol) of 1-chloro-3-nitropropane were added dropwise. After the dropwise addition, the temperature was raised to 100° C. to react for 1 hour, and then lowered to room temperature. The reaction solution was washed twice with water and separated. The organic phase was dried over anhydrous sodium sulfate and evaporated to dryness to obtain 5 g of a light yellow transparent liquid. It was confirmed as nitrocyclopropane by NMR analysis, with a yield of 89.1% and a purity of 95%.

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Abstract

The invention discloses a synthesis method of nitrocyclopropane. The synthesis method comprises the following steps: taking 1-halogenated-3-nitropropane as a raw material and taking benzyl triethyl ammonium chloride as a phase transfer catalyst under the action of sodium hydroxide to prepare the nitrocyclopropane. The method disclosed by the invention has the advantages of simplicity in operation,rapid reaction and high yield; the difficulty of rapidly and efficiently synthesizing the nitrocyclopropane is overcome; the synthesis method disclosed by the invention can be used for synthesizing an organic molecule containing a nitrocyclopropane structural unit.

Description

technical field [0001] The invention belongs to the field of synthesis of medicine and pesticide intermediates, and in particular relates to a synthesis method of nitrocyclopropane. Background technique [0002] Many compounds with cyclopropane structural units have good biological and physiological activities, and many intermediates in biological metabolism are derivatives of cyclopropane with cyclopropane structure. Cyclopropanes are widely used in drug design, especially nitro-containing cyclopropane compounds can be used to synthesize many heterocyclic drugs, peptide biopharmaceuticals and pesticides widely used in agriculture. [0003] The method (Helvetica Chimica Acta, 1982,65,137-161) of the synthetic nitrocyclopropane reported in the current literature is raw material with 1-iodo-3-nitrocyclopropane, the alkali that uses is potassium carbonate, and solvent is toluene, reflux reaction 2.75h, the product yield was 53%. This method has a low yield and has no applicat...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/05
Inventor 李秉擘卫天琪宁斌科王威陈涛杨翠凤张晓光张媛媛
Owner XIAN MODERN CHEM RES INST
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