CN106674213A - Preparation method of furilazole - Google Patents
Preparation method of furilazole Download PDFInfo
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- CN106674213A CN106674213A CN201510744762.7A CN201510744762A CN106674213A CN 106674213 A CN106674213 A CN 106674213A CN 201510744762 A CN201510744762 A CN 201510744762A CN 106674213 A CN106674213 A CN 106674213A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Abstract
The invention relates to a preparation method of furilazole. The method comprises the following steps: dropwisely adding furfural into a container filled with cyanotrimethylsilane and a catalyst, and uniformly stirring and mixing the solution; dropwisely adding the mixed solution into a non-protonic solvent containing lithium aluminum hydride; cooling the solution to room temperature, adding a sodium hydroxide solution to carry out neutralization reaction, and after the reaction finishes, carrying out filtration, drying and distillation to obtain a solid; adding an acetone/toluene sulfonic acid benzene solution into the solid, and stirring to carry out reflux reaction; finally adding sodium hydroxide and dichloroacetyl chloride into the solution, and stirring to react at -10-0 DEG C; and after the reaction finishes, pumping the solution into ice water, standing to stratify, and removing the water layer and oil layer, thereby finally obtaining the furilazole. The method has the advantages of reasonable preparation raw material selection and low cost. In the preparation process, the reflux reaction is firstly carried out at high temperature, and then standing and layering are carried out in a low-temperature place, thereby obtaining the furilazole. Thus, the method is convenient for preparation and high in efficiency.
Description
Technical field
The present invention relates to a kind of preparation method of furilazole, belongs to chemical substance preparation field.
Background technology
Dichloroacetyl oxazolidine compound is a kind of new herbicide-safener.It will be the developing direction of safener that safener forms new mixed agent with herbicide mixture, and the development of safener and it is beneficial to the exploitation of novel herbicide and the safe handling of herbicide using the research of technology, reduce because the use of herbicide is to the loss caused by agricultural production, it is beneficial to the sustainable development of agricultural production, but at present the reaction condition for preparing of furilazole has high demands, method is complicated, yield is low, therefore it is badly in need of a kind of reaction condition requirement of development low, method is simple and preparation method of the furilazole of efficiency high, Jing is retrieved, it was found that with same or analogous technical scheme of the invention.
The content of the invention
The technical problem to be solved in the present invention is to provide that a kind of reaction condition requirement is low, method simple and the preparation method of the furilazole of efficiency high.
To solve above-mentioned technical problem, the technical scheme is that：A kind of preparation method of furilazole, its innovative point is：The preparation method is specific as follows：
（1）Furtural is added drop-wise in the container equipped with cyano group trimethyl silane and catalyst, wherein the volume ratio of cyano group trimethyl silane and catalyst is 1:1～1.2, then solution is stirred and is well mixed；
（2）Mixed solution is added drop-wise in the non-protonic solvent equipped with lithium aluminium hydride reduction, being warming up to 50～65 DEG C carries out back flow reaction, and the reaction time is controlled to 2～3h；
（3）Solution is cooled into room temperature, and adds sodium hydroxide solution to be neutralized reaction, filtered after the completion of reaction, drying and distilling obtains solids；
（4）The benzole soln of acetone and toluenesulfonic acid is added in solids, and stirring carries out back flow reaction, the sulfur dioxide catalyst that volume fraction percent is 10～25% is then added thereto to again carries out catalytic reaction；
（5）Add NaOH and dichloroacetyl chloride in solution, the stirring reaction at -10～0 DEG C carries out stratification in suction frozen water again after the completion of reaction, removes water layer and oil reservoir finally obtains furilazole.
Further, the step（1）In catalyst be boron trifluoride.
It is an advantage of the current invention that：Preparing raw material select rationally, low cost, first back flow reaction is carried out by high temperature during preparation, then place and carry out at low temperature stratification, so as to obtain furilazole, prepare convenient and efficiency high.
Specific embodiment
Embodiment
1
The invention discloses a kind of preparation method of furilazole, the preparation method is specific as follows：
（1）Furtural is added drop-wise in the container equipped with cyano group trimethyl silane and boron trifluoride, wherein the volume ratio of cyano group trimethyl silane and boron trifluoride is 1:1, then solution is stirred and is well mixed；
（2）Mixed solution is added drop-wise in the non-protonic solvent equipped with lithium aluminium hydride reduction, being warming up to 50～60 DEG C carries out back flow reaction, and the reaction time is controlled to 2.5～3h；
（3）Solution is cooled into room temperature, and adds sodium hydroxide solution to be neutralized reaction, filtered after the completion of reaction, drying and distilling obtains solids；
（4）The benzole soln of acetone and toluenesulfonic acid is added in solids, and stirring carries out back flow reaction, the sulfur dioxide catalyst that volume fraction percent is 10～15% is then added thereto to again carries out catalytic reaction；
（5）Add NaOH and dichloroacetyl chloride in solution, the stirring reaction at -10～0 DEG C carries out stratification in suction frozen water again after the completion of reaction, removes water layer and oil reservoir finally obtains furilazole.
Embodiment
2
The invention discloses a kind of preparation method of furilazole, the preparation method is specific as follows：
（1）Furtural is added drop-wise in the container equipped with cyano group trimethyl silane and boron trifluoride, wherein the volume ratio of cyano group trimethyl silane and boron trifluoride is 1:1.2, then solution is stirred and is well mixed；
（2）Mixed solution is added drop-wise in the non-protonic solvent equipped with lithium aluminium hydride reduction, being warming up to 60～65 DEG C carries out back flow reaction, and the reaction time is controlled to 2～2.5h；
（3）Solution is cooled into room temperature, and adds sodium hydroxide solution to be neutralized reaction, filtered after the completion of reaction, drying and distilling obtains solids；
（4）The benzole soln of acetone and toluenesulfonic acid is added in solids, and stirring carries out back flow reaction, the sulfur dioxide catalyst that volume fraction percent is 15～25% is then added thereto to again carries out catalytic reaction；
（5）Add NaOH and dichloroacetyl chloride in solution, the stirring reaction at -10～0 DEG C carries out stratification in suction frozen water again after the completion of reaction, removes water layer and oil reservoir finally obtains furilazole.
Above-mentioned two embodiment can prepare furilazole, therefore optional above-mentioned preparation parameter is prepared.
The general principle and principal character of the present invention has been shown and described above.It should be understood by those skilled in the art that; the present invention is not restricted to the described embodiments; merely illustrating the principles of the invention described in above-described embodiment and specification; without departing from the spirit and scope of the present invention; the present invention also has various changes and modifications, and these changes and improvements are both fallen within scope of the claimed invention.The claimed scope of the invention is by appending claims and its equivalent thereof.
Claims (2)
1. a kind of preparation method of furilazole, it is characterised in that：The preparation method is specific as follows：
（1）Furtural is added drop-wise in the container equipped with cyano group trimethyl silane and catalyst, wherein the volume ratio of cyano group trimethyl silane and catalyst is 1:1～1.2, then solution is stirred and is well mixed；
（2）Mixed solution is added drop-wise in the non-protonic solvent equipped with lithium aluminium hydride reduction, being warming up to 50～65 DEG C carries out back flow reaction, and the reaction time is controlled to 2～3h；
（3）Solution is cooled into room temperature, and adds sodium hydroxide solution to be neutralized reaction, filtered after the completion of reaction, drying and distilling obtains solids；
（4）The benzole soln of acetone and toluenesulfonic acid is added in solids, and stirring carries out back flow reaction, the sulfur dioxide catalyst that volume fraction percent is 10～25% is then added thereto to again carries out catalytic reaction；
（5）Add NaOH and dichloroacetyl chloride in solution, the stirring reaction at -10～0 DEG C carries out stratification in suction frozen water again after the completion of reaction, removes water layer and oil reservoir finally obtains furilazole.
2. the preparation method of a kind of furilazole according to claim 1, it is characterised in that：The step（1）In catalyst be boron trifluoride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510744762.7A CN106674213A (en) | 2015-11-06 | 2015-11-06 | Preparation method of furilazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510744762.7A CN106674213A (en) | 2015-11-06 | 2015-11-06 | Preparation method of furilazole |
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| Publication Number | Publication Date |
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| CN106674213A true CN106674213A (en) | 2017-05-17 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201510744762.7A Pending CN106674213A (en) | 2015-11-06 | 2015-11-06 | Preparation method of furilazole |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110041294A (en) * | 2019-05-13 | 2019-07-23 | 河北科技大学 | The synthetic method and its application of the chloro- N- of 2,2- bis- [2- (2- furyl) -2- hydroxyethyl] acetamide |
-
2015
- 2015-11-06 CN CN201510744762.7A patent/CN106674213A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110041294A (en) * | 2019-05-13 | 2019-07-23 | 河北科技大学 | The synthetic method and its application of the chloro- N- of 2,2- bis- [2- (2- furyl) -2- hydroxyethyl] acetamide |
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| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20170517 |