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Preparation method of recessive malachite green hapten

A technology of recessive malachite green and hapten, which is applied in the field of immunochemistry, can solve the problems of cumbersome synthesis steps of recessive malachite green hapten, low final yield, and reduce the impact of antibodies, so as to reduce emissions and reaction by-products The effect of less and less organic solvent consumption

Active Publication Date: 2015-04-29
INST OF QUALITY STANDARD & TESTING TECH FOR AGRO PROD OF CAAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The key step in the synthesis of the recessive malachite green hapten is the extension of the active arm. In the existing synthesis methods, the active arm is extended by means of N, O or double bonds. The defect of this method is that the introduction of heteroatoms or other poles In theory, the spacer arm should generally be non-polar. Except for the active group for coupling, it should not contain other highly immunologically active structures, such as benzene rings, heteroatoms, hydroxyl groups, etc., to reduce the antibody Identification of the spacer arm and the effect of the spacer arm on the feature structure to be measured
The synthesis steps of the reported recessive malachite green hapten whose spacer arm is a saturated carbon chain are cumbersome and the final yield is low

Method used

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  • Preparation method of recessive malachite green hapten
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preparation example Construction

[0026] The invention provides a method for preparing a recessive malachite green hapten, the method comprising the following steps:

[0027] Step 1: carry out Heck reaction with 4-bromobenzaldehyde or 4-iodobenzaldehyde and acrolein diethyl acetal or the compound shown in general formula (I) in the presence of Heck reaction ligand, palladium acetate and acid-binding agent Compound 1 is obtained;

[0028] Step 2: Condensing compound 1 with N,N-dimethylaniline to obtain compound 2;

[0029] Step 3: dissolving compound 2 in 1,4-dioxane, adding saturated sodium hydroxide solution to a pH value of 9-10, and reacting to obtain the recessive malachite green hapten represented by general formula (II);

[0030]

[0031] Wherein, in the general formula (I), n is an integer of 1-3, and m is 0 or 1; in the general formula (II), n is an integer of 2-4.

[0032] In a preferred embodiment of the present invention, the recessive malachite green hapten is prepared by using acrolein diethy...

Embodiment 1

[0056] This example is used to illustrate the preparation method of the recessive malachite green hapten provided by the present invention.

[0057] Add 1.85g of 4-p-bromobenzaldehyde, 2.78g of tetrabutylammonium chloride and 0.067g of palladium acetate into a two-necked flask and mix well, then add N,N-dimethylformamide (DMF) under the protection of argon 40mL was used as the reaction solvent, and then 4.56mL of acrolein diethyl acetal and 2.79mL of triethylamine were added sequentially, stirred at 90°C (500rpm) for reaction, and a small amount was taken every 6 hours to judge the progress of the reaction by TLC. The reaction ended after 48h. The reaction solution was poured into 400 mL of ice water, stirred evenly, and then extracted with ethyl acetate 4 times, and the amount of ethyl acetate used each time was 150 mL. After the organic phase was dried by rotary evaporation, it was separated by column using petroleum ether: ethyl acetate = 4:1 as a developing solvent, and t...

Embodiment 2

[0067] Example 2 This example is used to illustrate the preparation method of the recessive malachite green hapten provided by the present invention.

[0068] Add 1.85g of 4-p-bromobenzaldehyde, 2.68g of triphenylphosphine and 0.067g of palladium acetate into a two-neck flask and mix evenly, and then add 40mL of N,N-dimethylformamide (DMF) under the protection of argon as Reaction solvent, then add 3.20mL of methyl 3-butenoate and 2.79mL of triethylamine in sequence, stir (500rpm) at 130°C for reaction, take a small amount every 6 hours and use TLC to judge the progress of the reaction. The reaction ends after about 30h. The reaction solution was poured into 400 mL of ice water, stirred evenly, and then extracted with ethyl acetate 4 times, and the amount of ethyl acetate used each time was 150 mL. After the organic phase was dried by rotary evaporation, it was separated by column using petroleum ether: ethyl acetate = 4:1 as a developing solvent, and the eluting solvent was ...

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Abstract

The invention relates to a preparation method of recessive malachite green hapten. The preparation method adopts the Heck reaction to lengthen an active arm, is mild in reaction conditions, adopts a small quantity of organic solvent, generates a small quantity of reaction byproducts and adopts simple operation steps; moreover, by optimizing a method for purifying the product, a great quantity of organic solvent is avoided being used in the purifying process and emission of environmental pollutants is effectively reduced.

Description

technical field [0001] The invention relates to the technical field of immunochemistry, in particular to a method for preparing a recessive malachite green hapten. Background technique [0002] Malachite Green (Malachite Green, MG) is a green crystal with metallic luster, easily soluble in water to form a blue-green solution, soluble in methanol, ethanol or amyl alcohol. MG is a synthetic triphenylmethane chemical that can be used not only as a dye for silk, leather and paper, but also as a biological dye. It is also a fungicide and has been widely used to prevent and treat various types of aquatic animals. Gill mold, saprolegniasis, and small melon worm disease. In May 2002, my country included malachite green in the "List of Veterinary Drugs and Compounds Prohibited by Food Animals", and formulated the use standard of malachite green in 2005, stipulating that in aquatic products, the detection rate of MG should not exceed 1μg / kg, but illegal use of malachite green occurre...

Claims

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Application Information

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IPC IPC(8): G01N33/531
CPCG01N33/531
Inventor 陈刚朱丹王凯强李强强逄秀梅魏丽娟
Owner INST OF QUALITY STANDARD & TESTING TECH FOR AGRO PROD OF CAAS
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