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Method for efficiently preparing cylopropyl ethylnen

A technology of cyclopropylacetylene and cyclopropylethane, applied in the field of chemistry, can solve the problems of low condensation yield, low product purity, difficult separation, etc., and achieve the effects of mild reaction conditions, high atom utilization, and simple post-processing

Inactive Publication Date: 2015-12-16
JIUJIANG ZHONGTIAN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0023] Patents US3715407, GB2329384 etc. have reported that triphenylphosphine reacts with phosgene to generate dichlorotriphenylphosphine as a chlorination reagent. The solubility of phosphine is very small, so a large amount of solvent is needed in the reaction. In addition, the application of phosgene brings a greater safety hazard to the industrialization of the product
In production, there must be an additional set of equipment for producing and storing phosgene, and there are still great safety hazards in the process
[0028] In summary, the common problems of the above traditional synthesis methods are: low condensation yield, low product purity, many by-products, and difficult separation. The organic amine catalyst used makes the wastewater contain more nitrogen-containing compounds, which is environmentally friendly. high pressure

Method used

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  • Method for efficiently preparing cylopropyl ethylnen
  • Method for efficiently preparing cylopropyl ethylnen
  • Method for efficiently preparing cylopropyl ethylnen

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Synthesis of intermediate 1,1-dichloro-1-cyclopropylethane (formula III)

[0049] Cyclopropylmethyl ketone (formula II): phosphorus pentachloride: catalyst is 1.0:1.0:1.0 according to the ratio of substances, cyclopropylmethyl ketone is 8.4g; phosphorus pentachloride is 20.8g; catalyst is methanol, and the mass of feed is 3.2g; the organic solvent is 8mL of dichloromethane, and its volume is 1 times the mass of cyclopropylmethyl ketone (mL / g).

[0050] In the reaction flask, add dichloromethane, turn on mechanical stirring, adjust the temperature to -10°C, and protect with nitrogen gas. Add phosphorus pentachloride and continue stirring. When the temperature of the feed liquid is stable, slowly add the mixture of cyclopropylmethyl ketone and methanol dropwise, and control the temperature of the feed liquid at -10 to 0°C. After the dropwise addition, the temperature was raised to 40°C, and samples were taken for gas phase monitoring every 1 h. After the rea...

Embodiment 2

[0053] Cyclopropylmethyl ketone: phosphorus pentachloride: catalyst is 1.0: 1.0: 0.4 feeding, cyclopropyl methyl ketone 8.4g; phosphorus pentachloride 20.8g; catalyst is isopropanol, feeding quality 2.4g ; The organic solvent is 34 mL of dichloromethane, and its volume is 4 times the mass of cyclopropylmethyl ketone (mL / g).

[0054] The reaction temperature was 0°C, and other operations were the same as in Example 1 to obtain 49.7 g of a dichloromethane solution of 1,1-dichloro-1-cyclopropylethane, of which 1,1-dichloro-1-cyclopropylethane The quality of alkane is 9.6g, and the yield is 69.1%.

Embodiment 3

[0056] Cyclopropylmethyl ketone: phosphorus pentachloride: catalyst is 1.0: 1.5: 1.2 feeding, cyclopropyl methyl ketone 8.4g; phosphorus pentachloride 31.2g; catalyst is isopropanol, feeding quality 7.2g ; The organic solvent is chloroform 42mL, and its volume consumption is 5 times of the mass of cyclopropylmethyl ketone (mL / g).

[0057] The reaction temperature was 25°C, and other operations were the same as in Example 1 to obtain 65.3 g of a chloroform solution of 1,1-dichloro-1-cyclopropylethane, in which 1,1-dichloro-1-cyclopropylethane The quality of alkane is 10.5g, and the yield is 75.5%.

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Abstract

The invention discloses a method for effectively preparing cylopropyl ethylnen as shown in the formula (I). The method comprises the steps that firstly, cylopropyl methyl ketone shown in the formula (II) is taken as a raw material and fully reacts in an organic solvent under the effect of phosphorus pentachloride and a catalyst, a reaction solution is subjected to reduced pressure distillation to obtain 1,1-dichloro-1-cylopropyl ethane as shown in the formula (III), an elimination reaction is then carried out under the effect of alkali, and a reaction solution is subjected to rectification and purification to obtain the product cylopropyl ethylnen. The method for effectively preparing the cylopropyl ethylnen has the advantages of being mild in reaction condition, high in yield, low in cost, little in three-waste and the like, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and in particular relates to a method for efficiently preparing cyclopropyne. Background technique [0002] Cyclopropyne is the key intermediate of Efavirenz, a specific anti-AIDS drug (WO9622955, US6235957). Efavirenz is a non-nucleoside reverse transcriptase inhibitor, which can be used in highly active antiretroviral therapy to treat class A human immune virus HIVTypeI. [0003] At present, there are many synthetic methods of cyclopropyne reported at home and abroad. According to the classification of different starting materials for preparation, there are mainly the following routes: [0004] (1) Using 5-chloro-1-pentyne as the starting material [0005] Using 5-chloro-1-pentyne as raw material, cyclopropylacetylene (WO9622955) was obtained by cyclization under the action of n-butyllithium, and the yield was 58%-65%. Although the reaction and post-treatment of this method are relatively...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C13/04C07C1/30
Inventor 夏建胜叶艺郑建华陈德响
Owner JIUJIANG ZHONGTIAN PHARMA
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