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Method for controlling synthesis end point of carbonyl diimidazole

A carbonyldiimidazole technology and a control method are applied in the control field of the synthetic end point of high-quality carbonyldiimidazole, and can solve the problems of high imidazole content, low yield and content, easy moisture absorption and dissolution of products, etc. The effect of simple process and high product yield

Pending Publication Date: 2022-03-22
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the method yield and content are not high, and product purification is difficult
[0011] The applicant found in the research that under the condition that the amount of phosgene added is appropriate, the quality of the carbonyldiimidazole product synthesized by method 1 is relatively the highest, and only the amount of phosgene added has a relatively large impact on the quality of the product. High, when the phosgene is excessive, the product is easy to absorb moisture and dissolve

Method used

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  • Method for controlling synthesis end point of carbonyl diimidazole
  • Method for controlling synthesis end point of carbonyl diimidazole
  • Method for controlling synthesis end point of carbonyl diimidazole

Examples

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Embodiment 1

[0047] A method for controlling the synthetic end point of carbonyldiimidazole of the present invention, comprising the following steps:

[0048] in N 2 Under protection, 41.3g (0.6mol, 99%) of imidazole and 400g of tetrahydrofuran were put into a 1000mL four-neck flask with a condenser, and the stirring was started. The reaction temperature was controlled at 10° C., and 118 g of a THF solution containing phosgene was added dropwise within 1 hour. The THF solution containing phosgene contained 18.0 g (0.1818 mol) of phosgene. After the addition of phosgene is completed, continue to stir and keep warm for 30 minutes, turn off the stirring and let stand for 10 minutes, take the supernatant of the reaction solution and quantitatively measure the chloride ion content to be 0.018%. According to the chloride ion content, 3.86 g of a tetrahydrofuran solution of imidazole with a mass fraction of 10% was quantitatively added dropwise while stirring. After the dropwise addition is com...

Embodiment 2

[0050] A method for controlling the synthetic end point of carbonyldiimidazole of the present invention, comprising the following steps:

[0051] in N 2 Under protection, 41.3g (0.6mol, 99%) of imidazole and 400g of tetrahydrofuran were put into a 1000mL four-neck flask with a condenser, and the stirring was started. The reaction temperature was controlled at 10° C., and 119.4 g of a tetrahydrofuran solution of phosgene containing 19.3 g (0.1949 mol) of phosgene was added dropwise within 1 hour. After the addition of phosgene was completed, after 30 minutes of heat preservation, the stirring was turned off and allowed to stand for 10 minutes, and the supernatant of the reaction solution was taken to quantitatively measure the chloride ion content to be 0.031%. According to the chloride ion content, 6.67 g of 10% imidazole in tetrahydrofuran solution was quantitatively added during stirring. After the dropwise addition was completed, the chloride ions in the reaction liquid c...

Embodiment 3

[0053] A method for controlling the synthetic end point of carbonyldiimidazole of the present invention, comprising the following steps:

[0054] in N 2 Under protection, 41.3g (0.6mol, 99%) of imidazole and 400g of tetrahydrofuran were put into a 1000mL four-neck flask with a condenser, and the stirring was started. The reaction temperature was controlled at 10° C., and 98 g of a phosgene-tetrahydrofuran solution containing 19.1 g (0.1929 mol) of phosgene was added dropwise within 1 hour. After the addition of phosgene was completed, after 30 minutes of heat preservation, the stirring was turned off and allowed to stand for 10 minutes, and the supernatant of the reaction solution was taken to quantitatively measure the chloride ion content to be 0.034%. According to the chloride ion content, 7.03 g of a tetrahydrofuran solution of 10 wt % imidazole was quantitatively added during stirring. After the dropwise addition was completed, the chloride ions in the reaction liquid c...

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Abstract

The invention discloses a carbonyl diimidazole synthesis endpoint control method which comprises the following steps: under the protection of N2, mixing a raw material imidazole and a solvent tetrahydrofuran, adding excessive phosgene under stirring for reaction, controlling the reaction temperature to be 5-10 DEG C, after the phosgene is added, keeping the temperature for 30-40 minutes under stirring, then standing for 10-15 minutes, and after the reaction is finished, cooling to room temperature to obtain the carbonyl diimidazole synthesis endpoint. Taking supernatant liquid of the reaction liquid, quantitatively determining the mass percentage content of chloride ions, quantitatively adding imidazole back under stirring according to the mass percentage content of the chloride ions, determining the chloride ions in the supernatant liquid of the reaction liquid again after adding, and filtering out imidazole hydrochloride under the protection of N2 after the reaction is finished, and evaporating the filtrate to remove the solvent at room temperature to obtain the imidazole. The carbonyl diimidazole product is obtained. The method disclosed by the invention has the advantages of high reaction efficiency, high product quality, no other redundant impurities and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a method for controlling the synthesis end point of high-quality carbonyldiimidazole. Background technique [0002] Carbonyldiimidazole is a compound with strong reactivity, it can react with -COOH, -NH 2 , -OH and other functional groups react to synthesize many compounds such as ketones, esters, ureas, etc., which are difficult to obtain by general methods. Because it can keep the molecular configuration unchanged and not form hydrohalic acid during the reaction, it is of great significance in biochemical synthesis. As a strong activator, carbonyldiimidazole is an important pharmaceutical intermediate, widely used in the synthesis of enzymes and protein adhesives, antibiotics, especially as a bonding agent for the synthesis of polypeptide compounds. With the rapid development of the field of biochemistry, N,N′-carbonyldiimidazole has been favore...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/60
CPCC07D233/60
Inventor 周锦萍李萍刘欢臧阳陵黄炜陈新年虞孝云
Owner HUNAN CHEM RES INST
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