CN102060795A - Method for synthesizing 1,3,5-triphenyltriazine - Google Patents
Method for synthesizing 1,3,5-triphenyltriazine Download PDFInfo
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- CN102060795A CN102060795A CN 201110007591 CN201110007591A CN102060795A CN 102060795 A CN102060795 A CN 102060795A CN 201110007591 CN201110007591 CN 201110007591 CN 201110007591 A CN201110007591 A CN 201110007591A CN 102060795 A CN102060795 A CN 102060795A
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- triphenyl
- triazine
- cyanobenzene
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- benzyl
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Abstract
The invention discloses a method for synthesizing 1,3,5-triphenyltriazine and relates to a method for synthesizing a class of compounds. The method comprises the following steps of: mixing 3-benzyl-5-(2-ethoxyl)-4-methylthiazolchlorate as a carbene catalyst, triethylamine, cyanobenzene and a solvent and then undergoing a radiation reaction for 10+/-5 minutes under the condition that the frequency of microwave radiation is 150-500Hz; or heating up the mixed liquid to a temperature of 50-100 DEG C, and then insulating heat for 30+/-10 minutes; after the reaction ends, evaporating out the solvent; and taking obtained solid and recrystallizing with alcohol to obtain the 1,3,5-triphenyltriazine. In the invention, the 3-benzyl-5-(2-ethoxyl)-4-methylthiazolchlorate is used as a catalyst which has no toxicity or harm to the environment and is an environmentally friendly catalyst. The method has the advantages of higher productivity and easiness of separation and purification.
Description
Technical field
The present invention relates to the synthetic method of a compounds, particularly a kind of synthetic method that contains triazine quasi-molecule between triphenyl and analogue thereof.
Background technology
1,3, the triazine compounds is the compound that a class has good direction structure between the 5-triphenyl.This compounds is at materials chemistry, and aspects such as molecular biology and medicine and pharmacology have very widely to be used.Pharmacology shows that this quasi-molecule has also shown good biological activity at anti-each quasi-cancer cell and aspect such as antiviral.Therefore this quasi-molecule has good DEVELOPMENT PROSPECT.
Existing 1,3, the synthetic method of triazine compounds all is to adopt cyanobenzene trimerization under the effect of strong acid or special catalyst to obtain between the 5-triphenyl.Such reaction needed is come catalyzed reaction to strong acid or expensive catalysts that environment has a significant impact, has very big application limitation, having not yet to see any bibliographical information can directly adopt cyanobenzene to synthesize 1,3 under the carbone catalyst effect, triazine compounds between the 5-triphenyl.
Summary of the invention
Purpose of the present invention just is to overcome the above-mentioned defective of existing production technology, development environmental protection, easily 1,3, triazine compounds synthetic method between the 5-triphenyl.
The present invention has two technical schemes:
One: after carbone catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol chlorate, triethylamine, cyanobenzene and solvent, it in the frequency of microwave radiation radioreaction 10 ± 5 minutes under the condition of 150～500Hz, then with the solvent evaporate to dryness, get the solid ethyl alcohol recrystallization, promptly get 1,3, triazine between the 5-triphenyl.
Another: after carbone catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol chlorate, triethylamine, cyanobenzene and solvent, the temperature that is heated to mixed solution is 50～100 ℃, soaking time is 30 ± 10 minutes again, then with the solvent evaporate to dryness, get the solid ethyl alcohol recrystallization, promptly get 1,3, triazine between the 5-triphenyl.
Two technical schemes of the present invention all are as reaction raw materials with carbone catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol chlorate, triethylamine, cyanobenzene, just the condition of reaction is inequality, one is reacted under microwave radiation, and another reacts under heating condition; But have identical advantage and effect:
1, the present invention is a catalyzer with 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol chlorate, and nontoxic, environmental sound is a kind of eco-friendly catalyzer.
2, productive rate of the present invention is higher, separates and purifies easily.
3, take the method for simple microwave radiation to replace conventional heating, can shorten the reaction times, cut down the consumption of energy, improve combined coefficient.
In order to improve the utilising efficiency of raw material, economize in raw materials, during production, the mass ratio that feeds intake of cyanobenzene and carbone catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol chlorate is 100 ︰ 27; The mass ratio that feeds intake of cyanobenzene and triethylamine is 100 ︰ 1.
Embodiment
Embodiment one: synthesize 1,3 with microwave irradiation, triazine between the 5-triphenyl:
1, with 2.7 mg carbone catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol chlorates, about 0.1 g of 1mmol() cyanobenzene, the about 0.001g of 0.01mmol() triethylamine and 10mL toluene (or benzene or dimethylbenzene) was added in the 50mL round-bottomed flask stirring at normal temperature 5 ± 1 minutes;
2, solution is placed into the chemical experiment that reflux condensing tube is housed and uses in the microwave oven, radiation is 10 ± 5 minutes under the frequency of 150-500Hz.
3, after reaction finished, with the solvent evaporate to dryness, solid can obtain final compound with ethyl alcohol recrystallization---and 1,3, triazine between the 5-triphenyl.
4, checking:
This product fusing point is 235-236oC, and is consistent with bibliographical information.
In addition, will be by 1,3, the product after the method for the bibliographical information of triazine is synthesized between the 5-triphenyl detects on TLC, and the inventive method synthetic product is detected on TLC, is same compound through comparison.
Embodiment two: synthesize 1,3 with heating method, triazine between the 5-triphenyl:
1, with 2.7 mg carbone catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol chlorates, about 0.1 g of 1mmol() cyanobenzene, the about 0.001g of 0.01mmol() triethylamine and 10mL toluene (or benzene or dimethylbenzene) was added in the 50mL round-bottomed flask stirring at normal temperature 5 ± 1 minutes;
2, mixing solutions is heated to 50～100 ℃, stirred 30 ± 10 minutes.
3, after reaction finished, with the solvent evaporate to dryness, solid can obtain final compound with ethyl alcohol recrystallization---and 1,3, triazine between the 5-triphenyl.
4, checking:
This product fusing point is 235-236oC, and is consistent with bibliographical information.
In addition, will be by 1,3, the product after the method for the bibliographical information of triazine is synthesized between the 5-triphenyl detects on TLC, and the inventive method synthetic product is detected on TLC, is same compound through comparison.
Conclusion: reaction equation of the present invention is as follows:
This reaction equation is represented: the different cyanobenzenes that are applicable to this method are for having the organic cyanobenzene compounds of various substituting groups.
Claims (5)
1.1,3, the synthetic method of triazine between the 5-triphenyl, it is characterized in that after carbone catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol chlorate, triethylamine, cyanobenzene and the solvent, is radioreaction 10 ± 5 minutes under the condition of 150～500Hz in the frequency of microwave radiation, then with the solvent evaporate to dryness, get the solid ethyl alcohol recrystallization, promptly get 1,3, triazine between the 5-triphenyl.
2.1,3, the synthetic method of triazine between the 5-triphenyl is characterized in that the temperature that is heated to mixed solution is 50～100 ℃ with after carbone catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol chlorate, triethylamine, cyanobenzene and the solvent, soaking time is 30 ± 10 minutes again, with the solvent evaporate to dryness, get the solid ethyl alcohol recrystallization then, promptly get 1,3, triazine between the 5-triphenyl.
3. according to claim 1 or 2 described 1,3, the synthetic method of triazine between the 5-triphenyl is characterized in that the mass ratio that feeds intake of described cyanobenzene and carbone catalyst 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazol chlorate is 100 ︰ 27.
4. according to claim 1 or 2 described 1,3, the synthetic method of triazine between the 5-triphenyl, the mass ratio that feeds intake that it is characterized in that described cyanobenzene and triethylamine is 100 ︰ 1.
5. according to claim 1 or 2 described 1,3, the synthetic method of triazine between the 5-triphenyl is characterized in that described solvent is any one in the benzene,toluene,xylene.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN2011100075911A CN102060795B (en) | 2011-01-14 | 2011-01-14 | Method for synthesizing 1,3,5-triphenyltriazine |
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| Application Number | Priority Date | Filing Date | Title |
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| CN2011100075911A CN102060795B (en) | 2011-01-14 | 2011-01-14 | Method for synthesizing 1,3,5-triphenyltriazine |
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| CN102060795A true CN102060795A (en) | 2011-05-18 |
| CN102060795B CN102060795B (en) | 2012-01-25 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103342686A (en) * | 2013-07-02 | 2013-10-09 | 扬州大学 | New epoxidation method of 2-benzylidene-1,3-indan diketone double bond |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1382687A (en) * | 2002-05-24 | 2002-12-04 | 清华大学 | Process for directly synthesizing pyrimidine, 1,3,5-triazine, phthalocyanine and polynitrile from nitrile |
| CN1396159A (en) * | 2001-07-12 | 2003-02-12 | 山西大学 | 2,4,6-trisubstituent-sym-triazine compound and its synthesizing process |
| WO2008085984A1 (en) * | 2007-01-08 | 2008-07-17 | Androscience Corporation | Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and uses thereof |
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2011
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1396159A (en) * | 2001-07-12 | 2003-02-12 | 山西大学 | 2,4,6-trisubstituent-sym-triazine compound and its synthesizing process |
| CN1382687A (en) * | 2002-05-24 | 2002-12-04 | 清华大学 | Process for directly synthesizing pyrimidine, 1,3,5-triazine, phthalocyanine and polynitrile from nitrile |
| WO2008085984A1 (en) * | 2007-01-08 | 2008-07-17 | Androscience Corporation | Compounds with (substituted phenyl)-propenal moiety, their derivatives, biological activity, and uses thereof |
Non-Patent Citations (2)
| Title |
|---|
| 《Heterocycles》 20050415 Xia Chen et al. Reactions of bis(silyl-substituted) methyllithium with alpha-hydrogen-free nitriles into 1,3,5-triazines 1425-1430 1-5 第65卷, 第6期 2 * |
| 《synthesis》 20040126 Antonio Herrera et al. A practical and easy synthesis of 2,4,6-trisubstituted-s-triazines 503-505 1-5 , 第4期 2 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103342686A (en) * | 2013-07-02 | 2013-10-09 | 扬州大学 | New epoxidation method of 2-benzylidene-1,3-indan diketone double bond |
| CN103342686B (en) * | 2013-07-02 | 2015-01-14 | 扬州大学 | New epoxidation method of 2-benzylidene-1,3-indan diketone double bond |
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| CN102060795B (en) | 2012-01-25 |
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