Method of preparing zeitin compound by applying ionic liquid

An ionic liquid and compound technology, applied in chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of poor N substitution reaction selectivity, long bromine dripping process, and difficulty in realizing industrialization. High selectivity, reducing the time for dripping bromine, and easy operation

Inactive Publication Date: 2014-01-22
BEIJING HARMONY CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] Li Yu and others have also considered using aceguvaldehyde dimethyl acetal to synthesize zeatin and dihydrozeatin as starting materials, but in the process, multiple reductions with lithium aluminum hydride, sodium borohydride, etc. are required, and the operation is complicated and the cost is high. It is also difficult to achieve industrialization
[0013] A method for preparing zeatin and its derivatives using isoprene as a starting material. The route is relat...

Method used

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  • Method of preparing zeitin compound by applying ionic liquid
  • Method of preparing zeitin compound by applying ionic liquid
  • Method of preparing zeitin compound by applying ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1: the preparation of ionic liquid

[0060] Ionic liquid [Bmim]Br 3 (i.e. 1-butyl-3-methylimidazole tribromide) preparation: 821g (10.0mol) of 1-methylimidazole was dissolved in 5L toluene, and 1437g (10.5mol) of 1-methylimidazole was added dropwise while stirring. Bromobutane, after the dropwise addition, heat to reflux for 24 hours, cool and stand still, separate the toluene, add 3L of ethyl acetate, and ultrasonicate while stirring, a large amount of white solid precipitates, filter, and wash the solid with ethyl acetate for 2 to 3 times , dried in vacuo to obtain ionic liquid [Bmim]Br (namely 1-butyl-3-methylimidazole bromide). Add 1440g (9.0mol) of bromine dropwise to [Bmim]Br while stirring, the mixture slowly turns from white to orange-yellow liquid, after the dropwise addition, continue to stir for 2 hours, add 1L of ethyl acetate to wash, then vacuum dry . Obtain orange-yellow ionic liquid [Bmim]Br 3 .

[0061] Ionic liquid [Emim]Br 3 (i.e. 1-e...

Embodiment 2

[0062] Example 2: One-pot preparation of (E)-4-(phthalimide)-2-methyl-2-butenyl acetate (i.e. compound III) with ionic liquid:

[0063]

[0064] (A) Add isoprene to the reaction kettle, control the temperature at -5°C to 25°C, add [Emim]Br dropwise 3 or [Bmim]Br 3 After the dropwise addition, continue to stir for 1 hour, distill off the excess isoprene, and the main product obtained is compound I, which is not treated, and continues to the next step of reaction.

[0065] (B) add dimethylformamide (DMF) in reactor, K 2 CO 3 , temperature control 0 ℃ ~ 25 ℃, while stirring, dropwise add the DMF solution of phthalimide; stir for about 6 hours, that is, the reaction ends when the phthalimide reaction is completed, and the main product obtained It is compound II, no treatment, continue to the next step reaction.

[0066] (C) Add sodium acetate (NaOAc) to the reaction solution in the previous step, heat to 80°C to 110°C, stir for 2 hours, finish the reaction with raw material...

Embodiment 3

[0067] Embodiment 3: the recovery of ionic liquid

[0068] Recovery of ionic liquid: in step (C) in embodiment 2, after toluene extracts organic compound, the main substance that obtains is ionic liquid [Emim]Br or [Bmim]Br, in this ionic liquid [Emim]Br or Add ethyl acetate to [Bmim]Br to wash for 2 to 3 times, and vacuum dry; then add bromine dropwise to [Emim]Br or [Bmim]Br to obtain [Emim]Br 3 or [Bmim]Br 3 , for repeated use.

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Abstract

The invention relates to a method of preparing a zeitin compound by applying ionic liquid. According to the method, isoprene is used as a starting material to carry out a one-pot reaction in the ionic liquid, i.e., (E)-4-(phthalimide)-2-methyl-2-butenyl acetate is obtained through bromination, selective nitrogen substitution as well as acetoxy substitution reaction, and then (E)-4-hydroxy-3-methyl-2-butenyl amine is obtained through hydrazinolysis and the zeitin compound is conveniently obtained through continuous reaction. The method disclosed by the invention has the advantages of being simple in synthesis route, green and environment-friendly, easy for industrialization, low in product cost as well as high in product purity at the same time, and the like.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for preparing zeatin compounds using ionic liquids. Background technique [0002] At the beginning of the 20th century, German botanist G. Haberlandt smashed plant phloem cells and placed them on the wound of potato tubers, and found that the parenchyma cells near the wound had split. In the 1940s, J.van.Overbeek, a plant physiologist in the United States, found that coconut milk (the endosperm of coconut) can stimulate the growth of Daturastramonium immature embryos cultured in vitro. They speculate that there are growth-promoting substances in coconut milk that are different from any known hormones. In the early 1950s, Miller et al. cultivated the parenchyma of tobacco plants in the laboratory. They found that parenchyma can grow into tumor-like clusters of cells called callus in vitro. Callus cells are generally larger, but do not divide. Sometimes the nucleus div...

Claims

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Application Information

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IPC IPC(8): C07H19/167C07H1/00C07D473/34
Inventor 韩见生李旭张杰
Owner BEIJING HARMONY CHEM TECH
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