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Method for preparing 1-proparagyl hydantoin

A technology of propargyl and propargyl glycine alkyl ester is applied in the field of preparation of 1-propargyl hydantoin, and achieves the effects of low production cost, reasonable process route and high purity

Inactive Publication Date: 2006-03-01
中山凯中有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The above methods have their own advantages and disadvantages in terms of process control and yield.

Method used

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  • Method for preparing 1-proparagyl hydantoin
  • Method for preparing 1-proparagyl hydantoin
  • Method for preparing 1-proparagyl hydantoin

Examples

Experimental program
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Effect test

Embodiment 1

[0030] (1) In the reactor with condensing reflux, stirring and dropping and heating device, add 142.3g ethyl glycine hydrochloride, 1000ml carbon tetrachloride, 212g triethylamine, stir, and heat up to 50~55°C, Slowly add 106g of 3-bromopropyne dropwise, react for 20 hours, filter the reactant, remove the solvent, distill under reduced pressure, collect fractions at 58-61°C / 300Pa to obtain 133 grams of light yellow oily liquid, yield 85%.

[0031] (2) 78g of the light yellow oily liquid obtained in the previous step is slowly added dropwise to 63g of 36% hydrochloric acid solution, and the reaction temperature is maintained at 25-30°C. After the dropwise addition, 47g of potassium cyanate aqueous solution is continued to be added dropwise, and the temperature is raised to 95-95°C after the dropwise addition. 100°C, keep warm for 5-6 hours, then cool down to 50°C, and enter the next step.

[0032] (3) Add 46 g of 20% hydrochloric acid dropwise to the mixed solution obtained in ...

Embodiment 2

[0034] (1) The operation process is the same as that of Example 1 step (1), changing glycine ethyl ester hydrochloride into glycine methyl ester hydrochloride, reacting for 30 hours, filtering the reactant, precipitating, and distilling under reduced pressure, collecting 54~57 °C / 300Pa fraction, 118 g of light yellow oily liquid was obtained, yield 83.5%.

[0035] (2) 71g of the light yellow oily liquid obtained in the previous step is slowly added dropwise to 60g of 36% hydrochloric acid solution, and the reaction temperature is maintained at 25-30°C. After the dropwise addition, 45g of potassium cyanate aqueous solution is continued to be added dropwise, and the temperature is raised to 95-95°C after the dropwise addition. 100°C, keep warm for 5-6 hours, then cool down to 50°C, and enter the next step.

[0036] (3) Add 46 g of 20% hydrochloric acid dropwise to the mixed solution obtained in the previous step to acidify it. After the drop is completed, the temperature is rais...

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Abstract

A process for preparing 1-propargyl glycolyurea uses the hydrochloride (or sulfate) of alkyl glycinate as raw material, and includes N-substitution, condensation and cyclization. Its advantages are high output rate and high purity.

Description

technical field [0001] The invention relates to a preparation method of 1-propargylhydantoin. Background technique [0002] Propargylhydantoin is an important pharmaceutical intermediate, which is widely used in the process of pharmaceutical synthesis, especially as an important raw material for the preparation of a new generation of ultra-high-efficiency pyrethroid imiprothrin. Its structural formula is as follows: [0003] [0004] At present, existing literature has reported the method for synthesizing 1-propargylhydantoin, and the more typical ones are as follows: [0005] (1) EP0560622, CN1032691, CN1078462, DE69329255, JP5255272 disclose a kind of raw material with hydantoin, react with morpholine, 37% formaldehyde solution in polar solvent at low temperature to obtain 3-morpholinomethylimidazolidine-2, 4-diketone, and then the resulting product reacts with propargyl methanesulfonate in a polar solvent under the action of a catalyst to obtain the target product. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/72
Inventor 谭如学胡应兵林彬
Owner 中山凯中有限公司