3-bromobutyl-5,5-dimethylhydantoin and preparation method thereof

A technology of dimethyl hydantoin and bromobutyl, applied in the field of 3-bromobutyl-5,5-dimethylbromobutyl hydantoin and its preparation, can solve the problems of long time-consuming and complicated operation, and achieve sterilization The effect is good, the synthesis process is optimized, and the sterilization speed is fast.

Inactive Publication Date: 2017-03-22
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current method for preparing alkylhydantoin is to generate the corresponding salt under the alkaline condition of alcohol, filter and dry, and then react with bromoalkane. The operation is more complicated and time-consuming.

Method used

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  • 3-bromobutyl-5,5-dimethylhydantoin and preparation method thereof
  • 3-bromobutyl-5,5-dimethylhydantoin and preparation method thereof
  • 3-bromobutyl-5,5-dimethylhydantoin and preparation method thereof

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preparation example Construction

[0032] A kind of preparation method of the present invention prepares 3-bromobutyl-5,5-dimethyl hydantoin, specifically comprises the following steps:

[0033] 1) 5,5-dimethylhydantoin is added to the acetone solution containing acid-binding agent, and the mass ratio of 5,5-dimethylhydantoin to acid-binding agent is: 1:(3- 5), stirring and refluxing to fully react;

[0034] Acid binding agent is anhydrous K 2 CO 3 , anhydrous Na 2 CO 3 , NaOH, KOH or triethylamine, the stirring and reflux time is 20-60min.

[0035] 2) Add 1,4-dibromobutane, control the water temperature and continue to reflux until fully reacted to make a solution, the molar ratio of 5,5-dimethyl hydantoin to 1,4-dibromobutane is 1:(1.5 -3); the reflux time is 3-7h, and the water temperature is 58°C-60°C;

[0036] 3) Suction filter the solution obtained in step 2) to remove inorganic salts, concentrate, add ethyl acetate and water for extraction and liquid separation, take the supernatant, remove ethyl a...

Embodiment 1

[0038] Dissolve 5,5-dimethylhydantoin (1g, 7.788mmol) in 70mL of acetone, stir to dissolve, add anhydrous K 2 CO 3 (4g), heated to reflux for 30min, then added 1,4-dibromobutane (3.37g, 15.6mmol) to the mixture, and continued to reflux for 5h to obtain a white suspension. The solvent was removed by rotary evaporation to obtain a clear viscous liquid.

[0039] Water and ethyl acetate were added thereto for extraction and liquid separation, and the supernatant was taken; after ethyl acetate was removed, column chromatography was performed using ethyl acetate / petroleum ether as the eluent. Collect the obtained liquid containing the product, and remove the eluent to obtain a white solid that is 3-bromobutyl-5,5-dimethylhydantoin, the structure of which is as follows: 1 H NMR (400MHz, CDCl 3 )δ5.94(s, 1H), 3.55(t, J=6.8Hz, 3H), 3.45(t, J=6.4Hz, 3H), 1.94–1.79(m, 6H), 1.70(s, 1H), 1.46(s, 8H).

Embodiment 2

[0041] Dissolve 5,5-dimethylhydantoin (1g, 7.788mmol) in 70mL of acetone, stir to dissolve, add anhydrous Na 2 CO 3 (4g), heated to reflux for 30min, then added 1,4-dibromobutane (3.37, 15.6mmol) to the mixture, and continued to reflux for 5h to obtain a white suspension. The solvent was removed by rotary evaporation to obtain a clear viscous liquid.

[0042] Water and ethyl acetate were added therein for extraction and liquid separation, and the supernatant was taken; after ethyl acetate was removed, column chromatography was performed with ethyl acetate / petroleum ether as eluent. The resulting liquid containing the product was collected, and the white solid obtained after removing the eluent was 3-bromobutyl-5,5-dimethylhydantoin, the structure of which was as follows: 1 H NMR (400MHz, CDCl 3 )δ5.94(s, 1H), 3.55(t, J=6.8Hz, 3H), 3.45(t, J=6.4Hz, 3H), 1.94–1.79(m, 6H), 1.70(s, 1H), 1.46(s, 8H).

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Abstract

The invention discloses 3-bromobutyl-5,5-dimethylhydantoin and a preparation method thereof. The preparation method comprises the following steps: adding 5,5-dimethylhydantoin (DMH) into an acetone solution of anhydrous potassium carbonate, carrying out refluxing for 30 minutes under stirring, then adding 1,4-dibromobutane into the mixed solution, keeping on refluxing for 5 hours, carrying out suction filtration, and concentrating the filtrate to obtain bromobutyl hydantoin. The disclosed 3-bromobutyl-5,5-dimethylhydantoin is an important intermediate in the synthesis of a quaternary ammonium type alkyl halamine antibacterial corrosion inhibitor, and has an industrial application prospect. According to the provided preparation method, the mole ratio of DMH to dibromobutane during the synthesis process, the kinds of acid binding agent, the mass ratio of DMH to acid binding agent, and the refluxing time before / after the addition of dibromobutane are optimized to improve the yield, proper reaction conditions are obtained, the preparation method is simple, and the raw materials are easily available.

Description

[0001] 【Technical field】 [0002] The invention belongs to the technical field of chemical industry, and in particular relates to 3-bromobutyl-5,5-dimethylbromobutylhydantoin and a preparation method thereof. [0003] 【Background technique】 [0004] For nearly half a century, with the continuous deterioration of the environment, pathogenic microorganisms have spread widely, leading to frequent public safety incidents. Therefore, antibacterial reagents and antibacterial material products have received more and more attention. The most widely used in various fields is the quaternary ammonium antibacterial agent, but due to a large number of long-term use, it will cause bacterial resistance and secondary pollution of the environment. [0005] Haloamines achieve the purpose of microbial inactivation by oxidizing or chlorinating intracellular protein receptors, so the possibility of drug resistance is very small. Therefore, haloamines are a kind of broad-spectrum bacteria with fast...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/72
CPCC07D233/72
Inventor 郭睿李云鹏郭煜马兰王映月宋博土瑞香王宁
Owner SHAANXI UNIV OF SCI & TECH
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