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Industrial production method of furan derivative

A technology of furan derivatives and furan rings, which is applied in organic chemistry and other fields, can solve the problems of long compound synthesis routes, uneconomical atoms, complex by-products, etc., and achieve the effects of green production process, low raw material cost and convenient post-processing

Inactive Publication Date: 2016-10-19
王志训
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, in the existing technology, the synthesis of this compound often has problems such as long synthetic route, complicated steps, complicated by-products, difficult separation, high cost, and uneconomical atoms.

Method used

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  • Industrial production method of furan derivative
  • Industrial production method of furan derivative
  • Industrial production method of furan derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The reaction equation is as follows:

[0048]

[0049] Put 9600g of compound A into the reactor, add 2700g of HCN, stir and react at room temperature for 5 hours, then add 600g of nickel, feed air (or oxygen), and heat the system at a speed of 2-4°C / min while stirring to 60°C, react for 8 hours, and stop the reaction. (The reaction method with catalyst participation can also be used in the reaction process with HCN, such as: metal catalyst, biocatalyst, Lewis, etc.)

[0050] Cool to room temperature, add 1 L of water, stir for 1 hour, adjust the pH to weak acidity, filter, and recrystallize twice with a solvent of acetone:cyclohexane=1:1 to obtain 12999 g of product B.

[0051] Or, after the above-mentioned reaction is finished, after cooling to room temperature, add 4700g of methoxyamine, adjust to an appropriate pH value with hydrochloric acid, and stir the reaction for 2 hours at room temperature, detect that the HPLC raw material is <5%, and feed 1700g of ammoni...

Embodiment 2

[0057] The reaction equation is as follows:

[0058]

[0059] Put 3000ml of acetonitrile, 9600g of compound A into the reaction kettle, add 4900g of NaCN and 100g of ion exchange resin at 25°C, stir and react for 1.5 hours, cool to room temperature, filter off the resin, evaporate the solvent, add 1L of water, and stir for 3 hours , add 100g of nickel, feed air (or oxygen), heat the system to 60°C at a speed of 2-4°C / min while stirring, react for 6 hours, and stop the reaction.

[0060] Cool to room temperature, add 1 L of water, stir for 1 hour, adjust the pH to weak acidity, filter, and recrystallize twice with a solvent of acetone:cyclohexane=1:1 to obtain 13132 g of product B.

[0061] Or, after the above-mentioned reaction is completed, after cooling to room temperature, add 4700g of methoxyamine, adjust to an appropriate pH value with hydrochloric acid, and stir the reaction for 2 hours at room temperature, detect that the HPLC raw material is <5%, and feed 1700g of amm...

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Abstract

The invention provides an industrial production method of a furan derivative. The industrial production method is characterized in that a compound A and a cyanide are subjected to an addition reaction, and an oxidation reaction and a hydrolysis reaction are performed to obtain the target furan derivative. According to the present invention, the production method is simple and different from the complex production way and the stringent production conditions in the prior art; the synthesis of the target product can be achieved through the one step; and the production process and the synthesis route are optimized, such that the advantages of less side reaction, convenient post-treatment and mild production condition during the production process are provided, and the method is suitable for the industrial production mode.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to an industrial production method of furan derivatives. Background technique [0002] Furan derivatives are widely used in various fields such as electronics, biology, medicine, materials, etc. In particular, furan ammonium salts are important intermediates for the preparation of antibiotics. [0003] For example, pyridyl furan derivatives are a class of compounds with protein kinase inhibitory activity, and these compounds can be used to treat various cancers: such as bladder cancer, breast cancer, colon cancer, renal cancer, liver cancer, lung cancer (including small cell lung cancer), Cancer of the esophagus, gallbladder, ovary, pancreas, stomach, cervix, thyroid, prostate, and skin (including squamous cell carcinoma); hematopoietic tumors of the lymphoid lineage, including leukemia, acute lymphoblastic leukemia, Acute lymphoblastic leukemia, B-cell lymphoma, T-cell lymphoma, H...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/54
CPCC07D307/54
Inventor 王志训
Owner 王志训
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