CN103880752A - Preparation of nitrogen heterocyclic compound metal salt or its heterocyclic compound complex - Google Patents
Preparation of nitrogen heterocyclic compound metal salt or its heterocyclic compound complex Download PDFInfo
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- CN103880752A CN103880752A CN201210563395.7A CN201210563395A CN103880752A CN 103880752 A CN103880752 A CN 103880752A CN 201210563395 A CN201210563395 A CN 201210563395A CN 103880752 A CN103880752 A CN 103880752A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
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Abstract
The invention relates to a synthetic method for preparing nitrogen heterocyclic compound metal salt and nitrogen heterocyclic compound metal salt heterocyclic compound complex. Under a solvent-free condition, nitrogen heterocyclic compounds are mixed with corresponding metal hydrides, and ball milling is carried out to obtain corresponding nitrogen heterocyclic compound metal salt; under the solvent-free condition, ball milling of a mixture of the nitrogen heterocyclic compounds, the corresponding metal hydrides, and heterocyclic compound ligands according to a certain ratio is carried out, or ball milling of a mixture of the nitrogen heterocyclic compound metal salt and a certain amount of heterocyclic compound ligands is carried out, so as to obtain nitrogen heterocyclic compound metal salt heterocyclic compound complex. The ball milling temperature is generally between -100 DEG C and 300 DEG C; the rotating speed is between 10 rpm and 500 rpm; the ball milling time is generally controlled to be 1-300 hours. The preparation method has the advantages of simplicity, practicality, no solvent, no reaction balance point, reaction thoroughness, reaction process monitorability, and easy amplification.
Description
Technical field
The invention belongs to the preparation field of preparation method's technology and unknown compound, particularly prepare nitrogen heterocyclic metal-salt (as: imidazole natrium) and heterogeneous ring compound title complex (as: imidazole natrium imidazoles) thereof based on ball milled.
Background technology
Nitrogen heterocyclic is the cyclic organic compounds that contains nitrogen heteroatom in ring structure, has alkalescence more.Much having bioactive compound is all nitrogen heterocyclic, as nitrogenous base of VITMAIN B1, Histidine, DNA (ATCG) etc.So nitrogen heterocyclic is the focus that organic synthesis and field of medicaments are paid close attention to always.
Nitrogen heterocyclic metal-salt is to be widely used in the intermediate that a class is often used in the process of synthesis of azacyclic compounds derivative, especially alkyl substitution.People can trace back to very early the research of this compounds, as " American Chemical Society's meeting will " (JACS, 84 (1): 43-51.1962 and JACS, 90 (16): 4232-4238.1968) just carried out report to its reaction and character.The repercussion study at present this compounds being participated in is a lot, but all do not study in great detail for its preparation always, particularly there is no the report of extensive preparation, so cause the price of this similar drug always high, as modal imidazole natrium is about 1300 yuan in the price of every 10 grams of Sigma-Aldrich company.The preparation of this compounds is normally carried out in organic solvent, and for the sample of expecting crystal form, this kind of method exists that solvent-oil ratio is large, operating process is loaded down with trivial details, length consuming time and reaction exist balance the shortcoming such as to be difficult to carry out completely.
Summary of the invention
The object of the invention is to propose a kind of practicable method that is suitable for preparing various nitrogen heterocyclic metal-salts, to overcome, in art methods, solvent-oil ratio is large, operating process is loaded down with trivial details, length consuming time and reaction exist balance the shortcoming such as to be difficult to carry out completely.
To achieve these goals, the present invention has adopted the technology of preparing based on ball milled, and its concrete technical scheme is as follows:
Under solvent-free condition, one or more nitrogen heterocyclics are mixed according to certain mol proportion with one or more metal hydrides, mechanical ball milling is had an effect it, and this effect can be considered as simple acid-base reaction.In the process of reaction, the mol ratio of nitrogen heterocyclic and metal hydride is between 1:20 to 20:1, can control speed of reaction by the method for ball milling temperature and rotational speed of ball-mill, temperature of reaction general control is between-100 ° of C to 300 ° of C, and rotational speed of ball-mill is generally between 10 rpms to 500 rpms.Degree is carried out in reaction can be by monitoring that the pressure change in ball grinder judges, Ball-milling Time general control is between 1 hour to 300 hours.
This method can be expanded, and for the exploitation of this class novel cpd of nitrogen heterocyclic metal-salt heterogeneous ring compound title complex and synthetic, synthesizing in traditional solvent reaction of this compound cannot realize.Concrete technical scheme has following two kinds:
Scheme one: under solvent-free condition, one or more nitrogen heterocyclics are mixed with one or more metal hydrides, the mol ratio that makes nitrogen heterocyclic and metal hydride is between 1:20 to 20:1, add a certain amount of heterogeneous ring compound part simultaneously, the mol ratio that makes heterogeneous ring compound part and atoms metal be 100:1 between 1:100, mechanical ball milling is had an effect it.In the process of reaction, can control speed of reaction by the method for ball milling temperature and rotational speed of ball-mill, temperature of reaction general control is within the scope of-100 ° of C to 300 ° of C, and rotational speed of ball-mill is generally between 10 rpms to 500 rpms.Degree is carried out in reaction can be by monitoring that the pressure change in ball grinder judges, Ball-milling Time general control is between 1 hour to 300 hours.
Scheme two: first, prepare as stated above nitrogen heterocyclic metal-salt, and then add a certain amount of heterogeneous ring compound part, the mol ratio that makes heterogeneous ring compound part and atoms metal be 100:1 between 1:100, mechanical ball milling is had an effect it.In the process of reaction, can control speed of reaction by the method for ball milling temperature and rotational speed of ball-mill, temperature of reaction is generally between-100 ° of C to 300 ° of C, and rotational speed of ball-mill is generally between 10 rpms to 500 rpms, and Ball-milling Time general control is between 1 hour to 300 hours.
In described preparation scheme, material therefor is easy deliquescence or oxidizable material above, and therefore operation must operate under dry inert atmosphere, for example N
2or in the glove box of Ar filling.
Nitrogen heterocyclic in this method is all nitrogen heterocyclics (comprising fused ring compound) and the derivative thereof that has reactive hydrogen on nitrogen heteroatom, as one or more in imidazole and its derivants (as glyoxal ethyline, 4-methylimidazole), pyrazoles and derivative, pyrroles and derivative thereof, tetramethyleneimine and derivative thereof, indoles and derivative thereof, purine and derivative thereof, carbazole and derivative thereof.
In this method, metal hydride can be one or more in alkalimetal hydride, alkaline earth metal hydride and transition metal hydride.
Alkalimetal hydride is one or more in lithium hydride, sodium hydride, potassium hydride KH.
Alkaline earth metal hydride is one or more in magnesium hydride, hydrolith.
Transition metal hydride is one or more in titanium hydride, zircoium hydride, zinc hydride.
In this method, heterogeneous ring compound part is to have lone-pair electron, can provide the heterogeneous ring compound (comprising nitrogen heterocyclic heterogeneous ring compound) that electronics carries out coordination, as: Furan and its derivatives, oxazole and derivative thereof, isoxazole and derivative thereof, pyrroles and derivative thereof, imidazole and its derivants, pyrazoles and derivative thereof, thiophene and derivatives, thiazole and derivative thereof, isothiazole and derivative thereof, pyridine and its derivatives, pyrans and derivative thereof, pyridazine and derivative thereof, pyrimidine and derivative thereof, pyrazine and derivative thereof, quinoline and its derivates, isoquinoline 99.9 and derivative thereof, pteridine and derivative thereof, acridine and derivative thereof, indoles and derivative thereof, purine and derivative thereof, one or more in carbazole and derivative thereof.
The feature of this method is: simple, solvent-free, reaction without trim point, carry out thoroughly, reaction carries out degree and can monitor, easily amplify.
Brief description of the drawings
Fig. 1 is the XRD spectra of the imidazole natrium of the imidazole natrium that makes and standard.
Fig. 2 is the XRD spectra of the imidazoles lithium that makes.
Fig. 3 is pyrroles's sodium of making and the XRD spectra of pyrroles's lithium.
Fig. 4 is the imidazole natrium imidazoles that makes according to scheme one and the XRD spectra of imidazoles lithium imidazoles.
Fig. 5 is the XRD spectra of the imidazole natrium imidazoles that makes according to scheme two.
Specific embodiment
The present invention adopts above-mentioned ball milled to prepare various nitrogen heterocyclic metal-salts and heterogeneous ring compound title complex thereof.By the following examples the present invention is described in detail, it is to be noted that the present invention is not limited to these embodiment.
Embodiment 1: the preparation of imidazole natrium
In glove box, take the imidazoles of 687mg and the sodium hydride of 252mg in same ball grinder.Note, now two kinds of samples can not contact.By after this ball grinder sealing, be carefully transferred on ball mill, under the condition of 50 ° of C, under 200rpm rotating speed, ball milling 5 hours.Reaction is carried out degree and can be realized by monitoring that ball grinder internal pressure changes.Fig. 1 is X-ray diffraction (XRD) spectrogram of made sample, can find out, coincide with the imidazole natrium diffraction peak in database, proves that we have synthesized imidazole natrium, and this preparation method's feasibility has been described.
Embodiment 2: the preparation of imidazoles lithium
In glove box, take the imidazoles of 687mg and the lithium hydride of 81mg in same ball grinder.Note, now two kinds of samples can not contact.By after this ball grinder sealing, be carefully transferred on ball mill, under the condition of 50 ° of C, under 200rpm rotating speed, ball milling 20 hours.Reaction is carried out degree and can be realized by monitoring that ball grinder internal pressure changes.Fig. 2 is X-ray diffraction (XRD) spectrogram of made sample, can find out, the diffraction peak of imidazoles and lithium hydride disappears, and the substitute is one group of new diffraction peak, proves to have formed new species, i.e. our target product imidazoles lithium.
Embodiment 3: the preparation of pyrroles's sodium, pyrroles's lithium
In glove box, take 252mg sodium hydride (or 81mg lithium hydride), measure 0.5ml pyrroles in same ball grinder.Note, now two kinds of samples can not contact.By after this ball grinder sealing, be carefully transferred on ball mill, under the condition of room temperature, under 150rpm rotating speed, ball milling 5 hours.Reaction is carried out degree and can be realized by monitoring that ball grinder internal pressure changes.Fig. 3 is made pyrroles's sodium and X-ray diffraction (XRD) spectrogram of pyrroles's lithium powder sample.
Embodiment 4: the preparation (scheme one) of imidazole natrium imidazoles, imidazoles lithium imidazoles
In glove box, take the imidazoles (wherein 343.5mg imidazoles is as heterogeneous ring compound part) of 687mg and the sodium hydride (or 41mg lithium hydride) of 126mg in same ball grinder.Note, now two kinds of samples can not contact.By after this ball grinder sealing, be carefully transferred on ball mill, under the condition of 50 ° of C, under 200rpm rotating speed, ball milling 5 hours (for imidazoles lithium imidazoles, ball milling 20h).Reaction is carried out degree and can be realized by monitoring that ball grinder internal pressure changes.Fig. 3 is made imidazole natrium imidazoles and the X-ray diffraction (XRD) of imidazoles lithium imidazoles powdered sample, and they are the novel coordination compoundes of a class, yet there are no report, and we are called nitrogen heterocyclic metal-salt heterogeneous ring compound title complex.
In glove box, take the imidazole natrium 450mg that makes in embodiment 1 and imidazoles 343.5mg(as heterogeneous ring compound part) in same ball grinder, by after this ball grinder sealing, carefully be transferred on ball mill, under the condition of 50 ° of C, under 150rpm rotating speed, ball milling 5 hours.Fig. 5 is X-ray diffraction (XRD) spectrogram of made sample, can find out, coincide with the imidazole natrium imidazoles diffraction peak making in embodiment 4.
Claims (9)
1. the preparation method of nitrogen heterocyclic metal-salt or its heterogeneous ring compound title complex, it is the preparation of nitrogen heterocyclic metal-salt or nitrogen heterocyclic metal-salt heterogeneous ring compound title complex, it is characterized in that:
Adopt ball milled, ball milling raw material is nitrogen heterocyclic and metal hydride, ball milling raw material is mixed in proportion and carries out ball milling, obtains nitrogen heterocyclic metal-salt;
Or, adopting ball milled, ball milling raw material is nitrogen heterocyclic, metal hydride and heterogeneous ring compound part, or ball milling raw material is nitrogen heterocyclic metal-salt and heterogeneous ring compound part; Ball milling raw material be mixed in proportion and carry out ball milling, obtaining nitrogen heterocyclic metal-salt heterogeneous ring compound title complex.
2. according to preparation method claimed in claim 1, it is characterized in that: ball milling temperature is between-100 ° C to 300 DEG C.
3. according to the preparation method described in claim 1 or 2, it is characterized in that: rotational speed of ball-mill is generally between 10 rpms to 500 rpms.
4. according to the preparation method described in claim 1 or 2, it is characterized in that: Ball-milling Time is generally between 1 hour to 300 hours.
5. according to the preparation method described in claim 1 or 2, it is characterized in that:
Raw material nitrogen heterocyclic is all nitrogen heterocyclics (comprising fused ring compound) and the derivative thereof that has reactive hydrogen on nitrogen heteroatom, as one or more in imidazole and its derivants (as glyoxal ethyline, 4-methylimidazole), pyrazoles and derivative, pyrroles and derivative thereof, tetramethyleneimine and derivative thereof, indoles and derivative thereof, purine and derivative thereof, carbazole and derivative thereof etc.;
Metal hydride can be one or two or more kinds in alkalimetal hydride, alkaline earth metal hydride and transition metal hydride;
Alkalimetal hydride is one or two or more kinds in lithium hydride, sodium hydride, potassium hydride KH;
Alkaline earth metal hydride is one or two or more kinds in magnesium hydride, hydrolith;
Transition metal hydride is one or two or more kinds in titanium hydride, zircoium hydride, zinc hydride.
6. according to the preparation method described in claim 1 or 2, it is characterized in that:
Raw material heterogeneous ring compound part is to have lone-pair electron, can provide the heterogeneous ring compound (comprising nitrogen heterocyclic) that electronics carries out coordination, as: Furan and its derivatives, oxazole and derivative thereof, isoxazole and derivative thereof, pyrroles and derivative thereof, imidazole and its derivants, pyrazoles and derivative thereof, thiophene and derivatives, thiazole and derivative thereof, isothiazole and derivative thereof, pyridine and its derivatives, pyrans and derivative thereof, pyridazine and derivative thereof, pyrimidine and derivative thereof, pyrazine and derivative thereof, quinoline and its derivates, isoquinoline 99.9 and derivative thereof, pteridine and derivative thereof, acridine and derivative thereof, indoles and derivative thereof, purine and derivative thereof, one or two or more kinds in carbazole and derivative thereof.
7. according to the preparation method described in claim 1 or 2, it is characterized in that:
In nitrogen heterocyclic metal-salt preparation process, the mol ratio ratio of nitrogen heterocyclic and hydride is between 1:20 to 20:1.
8. according to the preparation method described in claim 1 or 2, it is characterized in that:
In the preparation process of nitrogen heterocyclic metal-salt heterogeneous ring compound title complex, the mol ratio of nitrogen heterocyclic and hydride is between 1:20 to 20:1, and heterogeneous ring compound part and atoms metal mol ratio are that 100:1 is between 1:100.
9. according to the preparation method described in claim 1 or 2, it is characterized in that: the mol ratio of nitrogen heterocyclic metal-salt and heterogeneous ring compound part is that 100:1 is between 1:100.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104356363A (en) * | 2014-11-10 | 2015-02-18 | 天津翔盛粉末涂料有限公司 | Novel modified imidazole latent epoxy curing accelerator |
| CN108083986A (en) * | 2016-11-22 | 2018-05-29 | 中国科学院大连化学物理研究所 | Hybrid inorganic-organic materials and its preparation and the application in hydrogen storage |
| CN111423618A (en) * | 2020-05-20 | 2020-07-17 | 中国科学技术大学 | Nitrogen heterocyclic aromatic amine-metal ion complex flame retardant and application thereof in preparation of flame-retardant epoxy resin |
| CN112250582A (en) * | 2019-07-22 | 2021-01-22 | 中国科学院大连化学物理研究所 | Preparation method of amino metal compound and application of amino metal compound |
| CN113620919A (en) * | 2021-06-18 | 2021-11-09 | 浙江工业大学 | Mechanical ball-milling auxiliary synthesis method of 2-amino-3-cyano-4H-pyran compounds |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104356363A (en) * | 2014-11-10 | 2015-02-18 | 天津翔盛粉末涂料有限公司 | Novel modified imidazole latent epoxy curing accelerator |
| CN108083986A (en) * | 2016-11-22 | 2018-05-29 | 中国科学院大连化学物理研究所 | Hybrid inorganic-organic materials and its preparation and the application in hydrogen storage |
| CN108083986B (en) * | 2016-11-22 | 2020-08-04 | 中国科学院大连化学物理研究所 | Organic-inorganic hybrid material, preparation thereof and application thereof in hydrogen storage |
| CN112250582A (en) * | 2019-07-22 | 2021-01-22 | 中国科学院大连化学物理研究所 | Preparation method of amino metal compound and application of amino metal compound |
| CN111423618A (en) * | 2020-05-20 | 2020-07-17 | 中国科学技术大学 | Nitrogen heterocyclic aromatic amine-metal ion complex flame retardant and application thereof in preparation of flame-retardant epoxy resin |
| CN111423618B (en) * | 2020-05-20 | 2021-07-06 | 中国科学技术大学 | Nitrogen heterocyclic aromatic amine-metal ion complex flame retardant and application thereof in preparation of flame-retardant epoxy resin |
| CN113620919A (en) * | 2021-06-18 | 2021-11-09 | 浙江工业大学 | Mechanical ball-milling auxiliary synthesis method of 2-amino-3-cyano-4H-pyran compounds |
| CN113620919B (en) * | 2021-06-18 | 2023-12-12 | 浙江工业大学 | Mechanical ball milling assisted synthesis method of 2-amino-3-cyano-4H-pyran compound |
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