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Method of synthesizing p-N-imidazolyl benzaldehyde

A synthesis method and a technology for p-fluorobenzaldehyde, which are applied in directions such as organic chemistry, can solve the problems of increased production time and production cost, complicated and complicated separation methods, shortened synthesis time, etc., so as to achieve shortened production time, simple and feasible method, and reduced production time. cost reduction effect

Inactive Publication Date: 2010-02-17
QINGYUAN POLYTECHNIC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, the synthesis method of Cozzi in 1993 is more classic, using DMSO as solvent, potassium carbonate as catalyst, and the product is separated by column chromatography, but the yield is very low, and the separation method is cumbersome and complicated; Akira Tanaka improved the synthesis method in 1998, using DMF As a solvent, potassium carbonate is still used as a catalyst. Although the yield has increased by up to 55%, the product still needs to be separated and purified by column chromatography; in 2001, Peter Magdolen et al. used ultrasonic technology to shorten the synthesis time. The solvent is DMSO, the catalyst is potassium carbonate, and the productive rate is greatly improved, which can reach 75%. The product purification still needs to use column chromatography, which increases the production time and production cost

Method used

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  • Method of synthesizing p-N-imidazolyl benzaldehyde
  • Method of synthesizing p-N-imidazolyl benzaldehyde
  • Method of synthesizing p-N-imidazolyl benzaldehyde

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (1) Use DMF as a solvent, add imidazole and a catalyst, gradually heat up to 90°C, after 5min, add p-fluorobenzaldehyde dropwise three times, react at 80°C for 10 hours to obtain a reaction mixture;

[0024] Add 30ml DMF to a 100mL round bottom flask, weigh 3.4g (0.05mol) imidazole, 5.0g K 2 CO 3 Add the powder into the flask, stir, add 3 drops of phase transfer catalyst aliquat336 dropwise, and gradually raise the temperature to 90°C. After 5 minutes, add 5.4mL p-fluorobenzaldehyde dropwise in three times, the solution turns light yellow. After the dropwise addition, adjust the temperature is 80°C. After 10 hours, the heating was stopped.

[0025] (2) The reaction mixture was purified by freeze separation.

[0026] The cooled reaction mixture was poured into 150 mL of ice water, stirred, and a large amount of yellow precipitates appeared. Freeze at 0°C for 30 minutes to obtain more precipitates, filter them with suction, and dry them in vacuum to constant weight. T...

Embodiment 2

[0028] (1) Use DMF as a solvent, add imidazole and a catalyst, gradually heat up to 90°C, after 5min, add p-fluorobenzaldehyde dropwise three times, react at 80°C for 10 hours to obtain a reaction mixture;

[0029] Add 30ml DMF to a 100mL round bottom flask, weigh 3.4g (0.05mol) imidazole, 5.0g K 2 CO 3 Add the powder into the flask, stir, add 3 drops of phase transfer catalyst aliquat336 dropwise, and gradually raise the temperature to 90°C. After 5 minutes, add 5.4mL p-fluorobenzaldehyde dropwise three times, and the solution turns light yellow. After the dropwise addition, the temperature is adjusted to 80°C. After 10 hours, the heating was stopped.

[0030] (2) The reaction mixture was purified by freeze separation.

[0031] The cooled reaction mixture was poured into 160 mL of ice water, stirred, and a large amount of yellow precipitates appeared. Freeze at -5°C for 30 minutes to obtain more precipitates, filter with suction, and vacuum-dry to constant weight. It is l...

Embodiment 3

[0033] (1) Use DMF as a solvent, add imidazole and a catalyst, gradually heat up to 90°C, after 5min, add p-fluorobenzaldehyde dropwise three times, react at 80°C for 10 hours to obtain a reaction mixture;

[0034] Add 30ml DMF to a 100mL round bottom flask, weigh 3.4g (0.05mol) imidazole, 5.0g K 2 CO 3 Add the powder into the flask, stir, add 3 drops of phase transfer catalyst aliquat336 dropwise, and gradually raise the temperature to 90°C. After 5 minutes, add 5.4mL p-fluorobenzaldehyde dropwise three times, and the solution turns light yellow. After the dropwise addition, the temperature is adjusted to 80°C. After 10 hours, the heating was stopped.

[0035] (2) The reaction mixture was purified by freeze separation.

[0036] The cooled reaction mixture was poured into 180 mL of ice water, stirred, and a large amount of yellow precipitates appeared. Freeze at -18°C for 30 minutes to obtain more precipitates, filter with suction, and dry in vacuum to constant weight, and...

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Abstract

The present invention discloses synthetic method of p-N-glyoxalinyl benzaldehyde, which uses appropriate catalyst to increase specific surface area of synthesis reaction, and the invention provides acompletely new subzero fractionating and purifying method, which has the advantages of simply performing, high yield and low cost, and it lays foundation for industrialization production and extensiveapplication prospect of p-N-glyoxalinyl benzaldehyde.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a synthesis method of p-N imidazolylbenzaldehyde. Background technique [0002] p-N-imidazolylbenzaldehyde is an important pharmaceutical intermediate, which can be used to synthesize drugs for controlling cholesterol levels in humans, and is also an important coordination intermediate. [0003] The synthesis of p-N imidazolyl benzaldehyde is generally synthesized with p-fluorobenzaldehyde and imidazole, and the reaction is called S N Ar reaction. Among them, the synthesis method of Cozzi in 1993 is more classic, using DMSO as solvent, potassium carbonate as catalyst, and the product is separated by column chromatography, but the yield is very low, and the separation method is cumbersome and complicated; Akira Tanaka improved the synthesis method in 1998, using DMF As a solvent, potassium carbonate is still used as a catalyst. Although the yield has increased by up t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/60
Inventor 冯小军吴杰颖
Owner QINGYUAN POLYTECHNIC
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