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1,3-dichlor-6-trifluomethyl-9-phenanthrene formaldehyde preparation method

A technology of trifluoromethyl and formaldehyde, which is applied in the field of preparation of 1,3-dichloro-6-trifluoromethyl-9-phenanthrene formaldehyde, can solve the problems of harsh conditions, low melting point and low yield, and achieve The effect of mild reaction conditions, simple process operation and high product purity

Inactive Publication Date: 2006-05-03
ZHEJIANG NHU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Above method needs to use lead tetraacetate as oxygenant, has many shortcoming: 1, yield is not high, is 78-82%, and product purity is poor, and fusing point is on the low side; 2, lead tetraacetate waste residue and reaction waste residue all have a large amount of lead-containing Compounds, pollution control is difficult and costly; 3. Lead tetraacetate oxidation operation is difficult, conditions are harsh, water requirements are high, side reactions are many, and post-treatment is complicated

Method used

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Examples

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preparation example Construction

[0019] Preparation of active manganese dioxide

[0020] Dissolve 151 grams of manganese sulfate in 2.87 liters of hot water at 60°C, add a solution made of 105 grams of potassium permanganate and 2 liters of water under stirring, stir the mixture at 60°C for 1 hour, filter, and use the filter cake Wash with distilled water until the filtrate is colorless, dry the filter cake at 100-120°C, grind it finely to obtain 120 g, and store it in vacuum. Activate at 200°C for 1 hour before use.

Embodiment 1

[0022] In a 500 ml three-neck flask equipped with mechanical stirring and a thermometer, add 6.9 g of 1,3-dichloro-6-trifluoromethyl-9-phenanthrene methanol (0.02 mol) and 300 ml of dichloromethane, stir until dissolved, Add 13.9 grams (0.16 moles) of active manganese dioxide at 20°C, stir vigorously at 20°C for 24 hours, after the reaction is complete, filter, wash the filter cake with 3×200 ml of dichloromethane, combine the dichloromethane, and evaporate to dryness to obtain light yellow The solid was dried to obtain 6.0 g of the product, with a yield of 87.5%. Melting range 185.4~185.9℃, content 99.5% (HPLC).

Embodiment 2

[0024] Repeat the operation of Example 1, only change the amount of active manganese dioxide in Example 1 to 8.7 grams (0.1 mole), and the reaction time is 40 hours to obtain a product yield of 85.1%.

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Abstract

The invention discloses a preparation method for 1, 3-dichloro- 6- trifluoromethyl ¿C 9 - phenanthryl formaldehyde as intermediate of antimalarial agent by 1, 3-dichloro- 6- trifluoromethyl ¿C 9 ¿C phenanthryl carbinol with active manganese bioxide. This method is simple with mild reaction condition, and has high purity and yield.

Description

technical field [0001] The invention relates to a preparation method of 1,3-dichloro-6-trifluoromethyl-9-phenanthrene formaldehyde, an intermediate of phenanthrene methanol antimalarial drugs. Background technique [0002] Phenanthrene methanol antimalarial drugs are a class of effective malaria treatment drugs. As schizonticides, they have high killing activity against asexual endoerythrocytic Plasmodium. It is clinically used to treat single or mixed acute malaria caused by Plasmodium falciparum or Plasmodium vivax infection. Its representative drugs include halofantrine, debutylhalofantrine and so on. The structural formula of phenanthrene methanol antimalarial drugs is as follows: [0003] [0004] where R 1 is hydrogen, methyl, ethyl, propyl, butyl, R 2 For methyl, ethyl, propyl, butyl, phenyl, HX for hydrochloric acid, tartaric acid, oxalic acid, maleic acid. [0005] The key intermediate of phenanthrene methanol antimalarial drugs is ...

Claims

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Application Information

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IPC IPC(8): C07C47/55C07C45/29
Inventor 商志才车来滨钱洪胜陈云盛晓军
Owner ZHEJIANG NHU CO LTD
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