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Preparation method of guanidine polymer heterogeneous catalyst as well as application method of guanidine polymer heterogeneous catalyst to catalytic synthesis of Warfarin and derivatives thereof

A technology of a heterogeneous catalyst and an application method, applied in the application of catalytic synthesis of warfarin and its derivatives, the field of preparation of a guanidine polymer heterogeneous catalyst, can solve the problems of increasing the reaction cost and operation steps, and achieve mild conditions. , The effect of simple purification and wide application

Active Publication Date: 2019-01-08
HENAN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Catalysts commonly used to catalyze the synthesis of warfarin include some small molecule primary amine catalysts and thiourea catalysts. These catalysts are homogeneous catalysts. After the reaction, the catalyst needs to be separated from the product, which increases the reaction cost and operation steps.

Method used

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  • Preparation method of guanidine polymer heterogeneous catalyst as well as application method of guanidine polymer heterogeneous catalyst to catalytic synthesis of Warfarin and derivatives thereof
  • Preparation method of guanidine polymer heterogeneous catalyst as well as application method of guanidine polymer heterogeneous catalyst to catalytic synthesis of Warfarin and derivatives thereof
  • Preparation method of guanidine polymer heterogeneous catalyst as well as application method of guanidine polymer heterogeneous catalyst to catalytic synthesis of Warfarin and derivatives thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Example 1: Synthesis of Diphenyl-Substituted Guanidine Polymers

[0030] Take 1.86 g of aniline and 2.71 g of phenyl isothiocyanate dissolved in 50 mL of acetonitrile, stir at room temperature for 6 hours, a large amount of white precipitate appears, filter and dry to obtain 4.22 g of white solid, yield 92.5%.

[0031] Take 2.28 g of N,N'-diphenylthiourea obtained in the previous step, dissolve it in 50 mL of dichloromethane, then add 3.03 g of triethylamine, and finally add 5.11 g of 2-chloro-1-methyliodopyridine, Stir at room temperature for 30 minutes, filter, spin the filtrate to remove the solvent, and separate and purify by column chromatography (eluent: petroleum ether) to obtain 1.57 g of a colorless transparent liquid with a yield of 81.0%.

[0032] 1.57 g (about 8 mmol) of diphenylcarbodiimide obtained in the previous step was dissolved in 20 mL of dichloromethane, and 0.473 g of branched polyethyleneimine (1 mmol equivalent, molecular weight 10,000) was added...

Embodiment 2

[0034] Embodiment 2: the synthesis of phenyl, benzyl substituted guanidine polymer

[0035] Take 2.14 g of benzylamine and 2.71 g of phenyl isothiocyanate dissolved in 50 mL of acetonitrile, stir at room temperature for 6 hours, a large amount of white precipitate appears, filter and dry to obtain 4.56 g of white solid, yield 94.0%.

[0036] Take 2.42 g of thiourea obtained in the previous step, dissolve it in 50 mL of dichloromethane, then add 3.03 g of triethylamine, and finally add 5.11 g of 2-chloro-1-methyliodopyridine, stir at room temperature for 30 minutes, and filter. After the filtrate was spun to remove the solvent, it was separated and purified by column chromatography (eluent: petroleum ether) to obtain 1.66 g of a colorless transparent liquid with a yield of 79.8%.

[0037] 1.66 g (about 7.9 mmol) of the carbodiimide obtained in the previous step was dissolved in 20 mL of dichloromethane, and 0.473 g of branched polyethyleneimine (1 mmol equivalent, molecular wei...

Embodiment 3

[0039] Embodiment 3: the synthesis of phenyl, n-hexyl substituted guanidine polymer

[0040] 2.02 g of n-hexylamine and 2.71 g of phenylisothiocyanate were dissolved in 50 mL of acetonitrile, and stirred at room temperature for 6 hours, a large amount of white precipitate appeared, which was filtered and dried to obtain 4.12 g of white solid with a yield of 87.1%.

[0041] Take 2.36 g of thiourea obtained in the previous step, dissolve it in 50 mL of dichloromethane, then add 3.03 g of triethylamine, and finally add 5.11 g of 2-chloro-1-methyliodopyridine, stir at room temperature for 30 minutes, and filter. After the filtrate was spun to remove the solvent, it was separated and purified by column chromatography (eluent: petroleum ether) to obtain 1.26 g of a colorless transparent liquid with a yield of 62.3%.

[0042] 1.26 g (about 6.23 mmol) of the carbodiimide obtained in the previous step was dissolved in 20 mL of dichloromethane, and 0.368 g of branched polyethyleneimine ...

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Abstract

The invention discloses a preparation method of a guanidine polymer heterogeneous catalyst as well as an application method of the guanidine polymer heterogeneous catalyst to catalytic synthesis of Warfarin and derivatives thereof. The method comprises the following steps: synthesizing thiourea by taking various primary amino compounds and phenyl isothiocyanate as raw materials, converting the thiourea into corresponding carbodiimide by utilizing 2-chlorine-1-methyl iodide pyridine, performing stirring reaction on the carbodiimide and branched polyethyleneimine at room temperature, and synthesizing a polyethyleneimine-based guanidine polymer, wherein the obtained guanidine polymer can be purified by being washed in a solvent. The prepared guanidine polymer can efficiently catalyze additionreaction of 4-hydroxycoumarin and alpha, beta-unsaturated ketone; an anticoagulant Warfarin and derivatives thereof with the yield more than 90 percent can be obtained at room temperature; meanwhile,the catalyst can be reused, and efficient and environmentally-friendly effects can be achieved. The invention provides a new approach for synthesis of the anticoagulant Warfarin.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of a guanidine polymer heterogeneous catalyst and an application method thereof in catalytically synthesizing warfarin and its derivatives. Background technique [0002] Guanidine is a class of HNC (NH 2 ) 2 A general term for organic compounds with structural elements. Guanidine functional groups exist in organisms and in many drug molecules, such as L-arginine and metformin, a drug for treating diabetes. In organic chemistry, guanidine is used more as a strong base. Guanidine is one of the strongest organic bases. It is called a "superbase" and has strong nucleophilicity. As a strong base or catalyst, it has It is used in many types of organic reactions. However, due to their high polarity, the separation and purification of guanidine compounds are also very difficult, and the synthesis methods of guanidine are less and cumbersome, ...

Claims

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Application Information

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IPC IPC(8): C08G73/02C07D311/56B01J31/06
CPCB01J31/06B01J2231/32C07D311/56C08G73/0206
Inventor 董振华袁金伟肖咏梅毛璞
Owner HENAN UNIVERSITY OF TECHNOLOGY
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