CN104447776A - Novel heterocyclic organic compound and preparation method thereof - Google Patents
Novel heterocyclic organic compound and preparation method thereof Download PDFInfo
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- CN104447776A CN104447776A CN201310437329.XA CN201310437329A CN104447776A CN 104447776 A CN104447776 A CN 104447776A CN 201310437329 A CN201310437329 A CN 201310437329A CN 104447776 A CN104447776 A CN 104447776A
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- OEXKKRLCQHHKJP-UHFFFAOYSA-N COC1=CC(N)=CCC1 Chemical compound COC1=CC(N)=CCC1 OEXKKRLCQHHKJP-UHFFFAOYSA-N 0.000 description 1
- FOFUWJNBAQJABO-UHFFFAOYSA-N Oc1c(CCCN2CCC3)c2c3cc1 Chemical compound Oc1c(CCCN2CCC3)c2c3cc1 FOFUWJNBAQJABO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
Abstract
The invention relates to a novel heterocyclic organic compound and a preparation method thereof. According to the invention, a novel organic compound with a complicated structure is synthesized for the first time with such raw materials as 3-anisidine and trimellitic anhydride, the preparation final product is high in yield, good in crystallization effect and high in purity, and a high-purity guide sample and a sample are provided for subsequent chemical and biotic experiments. The invention further provides detailed synthesis and purification methods for the novel organic compound, and the production method is scientific and reasonable and provides detailed theoretical and practical guidance for subsequent expanded production.
Description
Technical field
The invention belongs to field of compound preparation, especially a kind of new type heterocycle organic compound and preparation method thereof.
Background technology
At present, because Bioexperiment makes new breakthroughs, make us in treatment and find in the process of the cause of disease, means are more, result is more accurate, property pharmaceutical requirements is also increased gradually so for the various disease for the treatment of, therefore, the various compound with New function is developed a large amount of, the whole world all has in searching the new compound resisting various difficult and complicated cases, in the process so developed at these new compounds, the compound of numerous new textures and new configuration can be produced, and then find useful in the new compound that these are numerous, there is the molecule for the treatment of use, therefore developing new compound is one and important process.
Summary of the invention
The object of the present invention is to provide a kind of novel organic compound and preparation method, the present invention synthesizes and this compound of purifying first, makes its purity reach certain requirement, further can test or application it.
The object of the invention is to be achieved through the following technical solutions:
New type heterocycle organic compound, its structural formula is as follows:
The preparation method of this compound is as follows:
(1) synthesis of intermediate 2
In single port bottle, add 3-anisidine, the chloro-3-N-PROPYLE BROMIDE of 1-, salt of wormwood, nitrogen protection mechanical stirring at 150 DEG C is spent the night.Washing, dichloromethane extraction, is spin-dried for, column chromatography for separation, obtains oily matter and is intermediate 2.The ratio of the chloro-3-N-PROPYLE BROMIDE of described 3-anisidine, 1-, salt of wormwood is 4g:15ml:20g.
(2) synthesis of intermediate 3
In single port bottle, add intermediate 2,48% Hydrogen bromide, be warming up to 120 DEG C under nitrogen protection, stirring is spent the night.TLC display reaction terminates, dilute with water, then is 6 with sodium hydroxide adjust pH, and dichloromethane extraction is spin-dried for, and obtains white solid and is intermediate 3.Described intermediate 1 and 48% hydrobromic ratio are 3g:10ml.
(3) synthesis of end product
In single port bottle, add intermediate 3, trimellitic acid 1,2-anhydride, Zinc Chloride Anhydrous, be heated to 180 DEG C under argon shield, be incubated 5 hours, TLC display reaction terminates.Reaction system is cooled, with the zinc chloride that dilute hydrochloric acid heating for dissolving is excessive, and bottom oily matter column chromatography is obtained the crude product that dissociates, then use dilute hydrochloric acid recrystallization, obtain product.The weight ratio of described intermediate 3, trimellitic acid 1,2-anhydride, Zinc Chloride Anhydrous is 9:5:10.
The structural formula of described intermediate 2 is
the structural formula of described intermediate 3 is
Advantage of the present invention and positively effect are:
1, the present invention uses the raw materials such as 3-anisidine, trimellitic acid 1,2-anhydride to synthesize the novel organic compound with complex construction first, the productive rate preparing end product is high, and crystallization effect is good, purity is high, for follow-up chemistry and Bioexperiment provide highly purified standard specimen or sample.
2, present invention also offers the detailed synthesis of this novel organic compound and purification process, production method science, rationally, for follow-up expanding production provides detailed theory and practice to instruct.
3, the invention provides synthesis condition, the raw material of each step in this novel organic compound building-up process, and the nuclear magnetic spectrum of synthesis after product, in building-up process, the analysis and identification of intermediate product provides detailed support.
Accompanying drawing explanation
Fig. 1 is the nuclear-magnetism figure of intermediate 2 of the present invention,
1h NMR (300MHz, CDCl3);
Fig. 2 is the nuclear-magnetism figure of intermediate 3 of the present invention,
1h NMR (300MHz, CDCl3);
Fig. 3 is the nuclear-magnetism figure of novel organic compound of the present invention,
1h NMR (300MHz, CDCl3);
Embodiment
Below in conjunction with embodiment, the present invention is further described, and following embodiment is illustrative, is not determinate, can not limit protection scope of the present invention with following embodiment.
Reaction scheme of the present invention is as follows:
Raw material
The raw materials such as 3-anisidine, trimellitic acid 1,2-anhydride are market and buy, without particular requirement.
The synthetic method of this compound is as follows:
(1) synthesis of intermediate 2
In 1000ml single port bottle, add 80g3-anisidine, the chloro-3-N-PROPYLE BROMIDE of 300ml1-, 400g salt of wormwood, be warming up to 150 DEG C of mechanical stirring under nitrogen protection and spend the night.Washing, dichloromethane extraction, is spin-dried for, column chromatography for separation, and obtaining intermediate 2 is oily matter 60g.
(2) synthesis of intermediate 3
In 500ml single port bottle, add 60g intermediate 2, then add the Hydrogen bromide of 200ml48%, be warming up to 120 DEG C under nitrogen protection, stirring is spent the night.TLC display reaction terminates, and with the dilution of 2L water, then be 6 with sodium hydroxide adjust pH, dichloromethane extraction is spin-dried for, and obtains white solid intermediate 3 product 50g.
(3) synthesis of end product
In 250ml single port bottle, add 18g intermediate 3,10g trimellitic acid 1,2-anhydride, 20g Zinc Chloride Anhydrous, be heated to 180 DEG C under argon shield, solid is molten state, is incubated 5 hours, and TLC display reaction is substantially complete.Reaction system is cooled, with the zinc chloride that the dilute hydrochloric acid heating for dissolving of 1N is excessive, and bottom oily matter column chromatography is obtained the free crude product of 6g, then use the dilute hydrochloric acid recrystallization of 1N, obtain 4g hydrochloride product.
Claims (4)
1. a new type heterocycle organic compound, is characterized in that: structural formula is as follows:
2. the preparation method of heterogeneous ring compound according to claim 1, is characterized in that: step is as follows:
(1) synthesis of intermediate 2
In single port bottle, add 3-anisidine, the chloro-3-N-PROPYLE BROMIDE of 1-, salt of wormwood, nitrogen protection mechanical stirring at 150 DEG C is spent the night.Washing, dichloromethane extraction, is spin-dried for, column chromatography for separation, obtains oily matter and is intermediate 2.
The ratio of the chloro-3-N-PROPYLE BROMIDE of described 3-anisidine, 1-, salt of wormwood is 4g:15ml:20g.
(2) synthesis of intermediate 3
In single port bottle, add intermediate 2,48% Hydrogen bromide, be warming up to 120 DEG C under nitrogen protection, stirring is spent the night.TLC display reaction terminates, dilute with water, then is 6 with sodium hydroxide adjust pH, and dichloromethane extraction is spin-dried for, and obtains white solid and is intermediate 3.
Described intermediate 2 and 48% hydrobromic ratio are 3g:10ml.
(3) synthesis of end product
In single port bottle, add intermediate 3, trimellitic acid 1,2-anhydride, Zinc Chloride Anhydrous, be heated to 180 DEG C under argon shield, be incubated 5 hours, TLC display reaction terminates.Reaction system is cooled, with the zinc chloride that dilute hydrochloric acid heating for dissolving is excessive, and bottom oily matter column chromatography is obtained the crude product that dissociates, then use dilute hydrochloric acid recrystallization, obtain product.
The weight ratio of described intermediate 3, trimellitic acid 1,2-anhydride, Zinc Chloride Anhydrous is 9:5:10.
3. preparation method according to claim 2, is characterized in that: the structure of described intermediate 2 is as follows:
4. preparation method according to claim 2, is characterized in that: the structure of described intermediate 3 is as follows:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310437329.XA CN104447776A (en) | 2013-09-23 | 2013-09-23 | Novel heterocyclic organic compound and preparation method thereof |
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| CN201310437329.XA CN104447776A (en) | 2013-09-23 | 2013-09-23 | Novel heterocyclic organic compound and preparation method thereof |
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| CN104447776A true CN104447776A (en) | 2015-03-25 |
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| CN201310437329.XA Pending CN104447776A (en) | 2013-09-23 | 2013-09-23 | Novel heterocyclic organic compound and preparation method thereof |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107880052A (en) * | 2017-11-02 | 2018-04-06 | 济南大学 | A kind of fluorescence probe for detecting hydrazine and its application |
| WO2021030525A1 (en) * | 2019-08-14 | 2021-02-18 | Valvoline Licensing And Intellectual Property Llc | Lubricant composition containing ashless tbn molecules |
-
2013
- 2013-09-23 CN CN201310437329.XA patent/CN104447776A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107880052A (en) * | 2017-11-02 | 2018-04-06 | 济南大学 | A kind of fluorescence probe for detecting hydrazine and its application |
| WO2021030525A1 (en) * | 2019-08-14 | 2021-02-18 | Valvoline Licensing And Intellectual Property Llc | Lubricant composition containing ashless tbn molecules |
| CN114341322A (en) * | 2019-08-14 | 2022-04-12 | 胜牌许可和知识产权有限公司 | Lubricant compositions containing ashless TBN molecules |
| US11345873B2 (en) | 2019-08-14 | 2022-05-31 | Valvoline Licensing And Intellectual Property Llc | Lubricant composition containing ashless TBN molecules |
| CN115261104A (en) * | 2019-08-14 | 2022-11-01 | 胜牌许可和知识产权有限公司 | Lubricant compositions containing ashless TBN molecules |
| CN114341322B (en) * | 2019-08-14 | 2022-12-16 | 胜牌许可和知识产权有限公司 | Lubricant compositions containing ashless TBN molecules |
| US11597891B2 (en) | 2019-08-14 | 2023-03-07 | Valvoline Licensing And Intellectual Property Llc | Lubricant composition containing Ashless TBN molecules |
| US11674104B2 (en) | 2019-08-14 | 2023-06-13 | Vgp Ipco Llc | Lubricant composition containing ashless TBN molecules |
| CN115261104B (en) * | 2019-08-14 | 2023-08-25 | 胜牌全球产品知识产权有限公司 | Lubricant composition containing ashless TBN molecules |
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