CN114230535A - Method for synthesizing triazine compound intermediate under catalysis of ionic liquid - Google Patents
Method for synthesizing triazine compound intermediate under catalysis of ionic liquid Download PDFInfo
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- CN114230535A CN114230535A CN202111673475.3A CN202111673475A CN114230535A CN 114230535 A CN114230535 A CN 114230535A CN 202111673475 A CN202111673475 A CN 202111673475A CN 114230535 A CN114230535 A CN 114230535A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/20—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with no nitrogen atoms directly attached to a ring carbon atom
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0282—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aliphatic ring, e.g. morpholinium
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Abstract
The invention discloses a method for synthesizing a triazine compound intermediate under the catalysis of ionic liquid, which comprises the following steps: the method comprises the steps of fully stirring and dissolving cyanuric chloride and an ionic liquid catalyst in an organic solvent, then dropwise adding a compound shown as a formula (II) to react for a period of time at a certain temperature to obtain a product, namely a compound shown as a formula (III)
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a method for synthesizing a triazine compound intermediate under the catalysis of an ionic liquid.
Background
Triazine compounds are widely applied to the fields of medicines, pesticides, cosmetics, high polymer materials and the like, and are important fine chemicals, and triazine ultraviolet absorbers have the advantages of broad spectrum, good effect, strong heat resistance, good dispersibility and the like, and are widely applied to the fields of cosmetics, plastics and the like.
The prior method for synthesizing the triazine compound mainly comprises a Grignard reagent method and a Friedel-crafts reaction method, and a Grignard reagent method is reported by Natingrena and the like (CN107635977A), wherein a Grignard reagent is prepared by magnesium powder and p-bromoanisole and then reacts with cyanuric chloride to synthesize the triazine compound, and the method has high yield, but has high raw material cost and high reaction risk; Wen-Feng Jiang et al (J.chem.Res, 2008, 11:664-665) report a Friedel-crafts reaction method, in which a triazine compound is obtained by catalyzing cyanuric chloride and anisole with Lewis acid aluminum trichloride, and the reaction is carried out for 18 hours at 25 ℃, which has the defects of low yield of target products, poor selectivity, easy generation of 2, 3 substituted by-products, difficult purification, long reaction time, serious three wastes and the like.
Disclosure of Invention
Aiming at the technical problems, the invention aims to provide a method for synthesizing a triazine compound intermediate under the catalysis of ionic liquid.
In order to achieve the purpose, the following technical scheme is provided:
a method for synthesizing a triazine compound intermediate under the catalysis of ionic liquid comprises the following steps: the method comprises the steps of fully stirring and dissolving cyanuric chloride and an ionic liquid catalyst shown as a formula (I) in an organic solvent, then dropwise adding a compound shown as a formula (II) to react for a period of time under a certain temperature condition to obtain a product, namely a compound shown as a formula (III),
the invention adopts chloroaluminate ionic liquid as a catalyst, and the possible reaction mechanism is as follows: under the action of ionic liquid catalyst, cyanuric chloride forms acyl carbocation, and aromatic ring compound is used as electrophilic reagent to attack acyl carbocation to generate SN2The substitution reaction forms HCl to remove chloride ions to generate a primary substitution product, and because the imidazole chloroaluminate ionic liquid has large molecules and large steric hindrance, the secondary reaction or the tertiary substitution reaction is difficult to occur,the reaction selectivity and yield are improved.
Further, in the formula (I), a substituent R1Is bromoethyl, bromobutyl, bromopropyl, bromopentyl or bromohexyl; in the formulae (II) and (III), the substituent R2Is hydrogen, methyl, hydroxy, methoxy or benzene, substituent R3Is hydrogen, methyl or hydroxy.
Furthermore, the molar feeding ratio of the raw material shown as the formula (II) to the cyanuric chloride is 1:0.5-1.5, preferably 1: 0.8-1.2.
Furthermore, the molar ratio of the raw material shown in the formula (II) to the ionic liquid catalyst is 1:0.5-2, preferably 1: 1-1.5.
Further, the organic solvent is dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride or chlorobenzene.
Further, the reaction temperature is controlled at 20 to 100 ℃ and preferably 40 to 80 ℃.
Further, the reaction time is controlled to be 1 to 12 hours, preferably 4 to 9 hours.
Compared with the prior art, the invention has the beneficial effects that:
1) compared with the traditional aluminum chloride catalyst, the ionic liquid is in a liquid state at room temperature, has better solubility, is easier to react with cyanuric chloride to form a complex, and shortens the reaction time.
2) The chlorine atom of the cyanuric chloride forms a complex with the ionic liquid through coordination catalysis, and the ionic liquid has larger molecular volume, so that the steric hindrance of the complex is increased after the complex is formed, the occurrence of secondary and tertiary substitution reactions is reduced, and the selectivity is improved to a great extent.
3) The post-reaction treatment is simple, the ionic liquid catalyst can be recycled, the discharge amount of three wastes is reduced, and energy conservation and consumption reduction are realized.
Detailed Description
The present invention is further illustrated by the following examples, which should not be construed as limiting the scope of the invention.
Example 1:
adding 20.29g (0.11mol) of cyanuric chloride and 38.72g (0.11mol) of bromo-1-methyl-3-butyl chloroaluminate imidazole ionic liquid into a 250mL round-bottom flask (the molar charge ratio of anisole to ionic liquid is 1:1.1, and the molar charge ratio of anisole to cyanuric chloride is 1:1.1), adding 150mL of 1, 2-dichloroethane under the protection of nitrogen, heating to 60 ℃, slowly dropwise adding 10.8g (0.1mol) of anisole, reacting for 6 hours, stopping the reaction, distilling to remove the solvent, adding the solvent into the residue for extraction (petroleum ether: ethyl acetate is 50:1), separating, recycling the ionic liquid at the lower layer, distilling under reduced pressure in the organic layer at the upper layer to remove the solvent to obtain a white crude product, recrystallizing (the solvent is ethyl acetate), filtering and drying in vacuum to obtain 11.25g of pure 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine in 45.21% yield and 99% purity.
Example 2:
referring to example 1, except for the fact that "melamine 9.225g (0.05mol) was added (anisole: melamine molar charge ratio 1: 0.5)", the other conditions and procedures were the same as in example 1, the objective 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was obtained in a yield of 24.56% and a purity of 99%.
Example 3:
referring to example 1, except for the "addition of 14.76g (0.08mol) of cyanuric chloride (anisole: cyanuric chloride molar charge ratio of 1: 0.8)", the other conditions and procedures were the same as in example 1, the objective 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was obtained in a yield of 30.12% and a purity of 99%.
Example 4:
referring to example 1, except for the fact that "cyanuric chloride 22.08g (0.12mol) (anisole: cyanuric chloride molar charge ratio 1: 1.2)" was added, the other conditions and operation were the same as in example 1, the objective 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained with a product yield of 45.78% and a purity of 99%.
Example 5:
referring to example 1, except for the fact that "melamine 27.68g (0.15mol) was added (anisole: melamine molar charge ratio 1: 1.5)", the other conditions and operation were the same as in example 1, the objective 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained in 45.96% yield and 99% purity.
Example 6:
referring to example 1, except for the difference that "bromo 1-methyl-3-butyl chloroaluminate imidazole ionic liquid 17.6g (0.05mol) (anisole: ionic liquid molar charge ratio 1: 0.5)", the other conditions and operation procedures were the same as in example 1, the target product 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained with a product yield of 10.30% and a purity of 99%.
Example 7:
referring to example 1, except for the difference that "bromo 1-methyl-3-butyl chloroaluminate imidazole ionic liquid 35.2g (0.1mol) (anisole: ionic liquid molar charge ratio 1: 1)", the other conditions and operation procedures were the same as in example 1, the target product 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained with a product yield of 35.42% and a purity of 99%.
Example 8:
referring to example 1, except for the difference that "bromo 1-methyl-3-butyl chloroaluminate imidazole ionic liquid 70.4g (0.2mol) (anisole: ionic liquid molar charge ratio 1: 2)", the other conditions and operation procedures were the same as in example 1, the target product 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained with a product yield of 44.47% and a purity of 99%.
Example 9:
referring to example 1, except for the difference that "bromo 1-methyl-3-butyl chloroaluminate imidazole ionic liquid 52.8g (0.15mol) (anisole: ionic liquid molar charge ratio 1: 1.5)", the other conditions and operation procedures were the same as in example 1, the target product 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained with a product yield of 44.85% and a purity of 99%.
Example 10:
referring to example 1, except for the difference that "the anisole was replaced by 9.214g (0.1mol) of toluene and the molar charge ratio of toluene to cyanuric chloride was 1: 1.1", the other conditions and procedures were the same as in example 1, to finally obtain the desired product 2, 4-dichloro-6- (4-methylphenyl) -1,3, 5-triazine with a yield of 30.25% and a purity of 99%.
Example 11:
referring to example 1, except that "9.412 g (0.1mol) of phenol was used instead of anisole, the molar charge ratio of phenol to cyanuric chloride was 1: 1.1", other conditions and procedures were the same as in example 1, to finally obtain the desired product 2, 4-dichloro-6- (4-hydroxyphenyl) -1,3, 5-triazine in 52.15% yield and 99% purity.
Example 12:
referring to example 1, except for the difference that "the anisole was replaced with 14.42g (0.1mol) of 1-naphthol, the molar charge ratio of 1-naphthol to cyanuric chloride was 1: 1.1", other conditions and procedures were the same as in example 1, to finally obtain the objective 2, 4-dichloro-6- (4- α -naphthol) -1,3, 5-triazine with a yield of 35.42% and a purity of 99%.
Example 13:
referring to example 1, except that "17.82 g (0.1mol) of anthracene was used instead of anisole, the molar charge ratio of 1-naphthol to cyanuric chloride was 1: 1.1", other conditions and procedures were the same as in example 1, to finally obtain the objective 2, 4-dichloro-6- (4- α -naphthol) -1,3, 5-triazine in 63.25% yield and 99% purity.
Example 14:
referring to example 1, except for the fact that "35.69 g (0.11mol) of bromo 1-methyl-3-butyl chloroaluminate imidazole ionic liquid was substituted for the bromo 1-methyl-3-butyl chloroaluminate imidazole ionic liquid (anisole: ionic liquid molar charge ratio of 1: 1.1)", other conditions and procedures were the same as in example 1, the objective 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained with a yield of 44.70% and a purity of 99%.
Example 15:
referring to example 1, except for the fact that "40.30 g (0.11mol) of bromo 1-methyl-3-pentyl chloroaluminate imidazole ionic liquid was used instead of the bromo 1-methyl-3-butyl chloroaluminate imidazole ionic liquid (anisole: ionic liquid molar charge ratio of 1:1.1)," the other conditions and procedures were the same as in example 1, the objective 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained with a yield of 28.75% and a purity of 99%.
Example 16:
referring to example 1, except for the point that "the bromo 1-methyl-3-butyl chloroaluminate imidazole ionic liquid (anisole: ionic liquid molar charge ratio of 1:1.1) was replaced by 41.84g (0.11mol) of the bromo 1-methyl-3-hexyl chloroaluminate imidazole ionic liquid", the other conditions and operation procedures were the same as in example 1, the target product 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained with a product yield of 28.65% and a purity of 99%.
Example 17:
referring to example 1, except for the fact that "35.24 g (0.1mol) of bromo-1-methyl-3-butyl chloroaluminate imidazole ionic liquid was added (anisole: ionic liquid molar charge ratio 1: 1)", the other conditions and operation were the same as in example 1, the target product 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained with a product yield of 41.07% and a purity of 99%.
Example 18:
referring to example 1, except for the fact that "49.36 g (0.14mol) of bromo-1-methyl-3-butyl chloroaluminate imidazole ionic liquid (anisole: ionic liquid molar charge ratio 1: 1.4)" was added, the other conditions and operation were the same as in example 1, the desired product, 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine, was finally obtained in a yield of 43.43% and a purity of 99%.
Example 19:
referring to example 1, except for "replacing 1, 2-dichloroethane with dichloromethane", the other conditions and procedures were the same as in example 1, and the objective 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained in 35.64% yield and 99% purity.
Example 20:
referring to example 1, except for the difference that "1, 2-dichloroethane was replaced with chloroform", other conditions and procedures were the same as in example 1, and the objective 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained with a product yield of 10.43% and a purity of 99%.
Example 21:
referring to example 1, except for the difference that "1, 2-dichloroethane was replaced with chlorobenzene", other conditions and procedures were the same as in example 1, and the objective 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained in a yield of 24.62% and a purity of 99%.
Example 22:
referring to example 1, except for the fact that "the reaction temperature was changed to 50 ℃", the other conditions and the operation were the same as in example 1, and the desired product, 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine, was finally obtained in a yield of 35.5% and a purity of 99%.
Example 23:
referring to example 1, except that "the reaction temperature was changed to 80 ℃", the other conditions and operation were the same as in example 1, and the desired product, 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine, was finally obtained in a yield of 31.09% and a purity of 99%.
Example 24:
referring to example 1, except that "the reaction time was changed to 4 hours", other conditions and operation were the same as in example 1, and the objective 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained in a yield of 21.01% and a purity of 99%.
Example 25:
referring to example 1, except that "the reaction time was changed to 8 hours", other conditions and operation were the same as in example 1, and the objective 2, 4-dichloro-6- (4-methoxyphenyl) -1,3, 5-triazine was finally obtained in 39.73% yield and 99% purity.
The statements in this specification merely set forth a list of implementations of the inventive concept and the scope of the present invention should not be construed as limited to the particular forms set forth in the examples.
Claims (9)
1. A method for synthesizing a triazine compound intermediate under the catalysis of ionic liquid is characterized by comprising the following steps: the method comprises the steps of fully stirring and dissolving cyanuric chloride and an ionic liquid catalyst shown as a formula (I) in an organic solvent, then dropwise adding a compound shown as a formula (II) to react for a period of time under a certain temperature condition to obtain a product, namely a compound shown as a formula (III),
2. the method for synthesizing the intermediate of triazine compounds catalyzed by ionic liquid as claimed in claim 1, wherein in the formula (I), the substituent R is1Is bromoethyl, bromobutyl, bromopropyl, bromopentyl or bromohexyl; in the formulae (II) and (III), the substituent R2Is hydrogen, methyl, hydroxy, methoxy or benzene, substituent R3Is hydrogen, methyl or hydroxy.
3. The method for synthesizing the triazine compound intermediate under the catalysis of the ionic liquid as claimed in claim 1, wherein the molar charge ratio of the raw material shown as the formula (II) to the cyanuric chloride is 1: 0.5-1.5.
4. The method for synthesizing the triazine compound intermediate under the catalysis of the ionic liquid as claimed in claim 4, wherein the molar charge ratio of the raw material shown as the formula (II) to the cyanuric chloride is 1: 0.8-1.2.
5. The method for synthesizing the intermediate of triazine compounds under the catalysis of ionic liquid according to claim 1, wherein the molar ratio of the raw material shown in formula (II) to the ionic liquid catalyst is 1: 0.5-2.
6. The method for synthesizing the intermediate of triazine compounds under the catalysis of ionic liquid according to claim 5, wherein the molar ratio of the raw material shown in formula (II) to the ionic liquid catalyst is 1: 1-1.5.
7. The method for synthesizing triazine compound intermediate under the catalysis of ionic liquid as claimed in claim 1, wherein the organic solvent is dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride or chlorobenzene.
8. The method for synthesizing the triazine compound intermediate under the catalysis of the ionic liquid as claimed in claim 1, wherein the reaction temperature is controlled to be 20-100 ℃, preferably 40-80 ℃.
9. The method for synthesizing the triazine compound intermediate under the catalysis of the ionic liquid as claimed in claim 1, wherein the reaction time is controlled to be 1-12 hours, preferably 4-9 hours.
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| CN101041642A (en) * | 2007-04-29 | 2007-09-26 | 浙江工业大学 | Method for synthesizing 4,6-disubstituted amido-1,3,5-triazine derivative |
| CN107746389A (en) * | 2017-09-14 | 2018-03-02 | 江苏丹霞新材料有限公司 | The method that Fu Ke methods are prepared to the catalyst recycling in aryl s-triazine UV absorbers |
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| CN109180597A (en) * | 2018-09-03 | 2019-01-11 | 中昊(大连)化工研究设计院有限公司 | A kind of preparation method of 2- (2,4- dihydroxy phenyl) -4,6- diphenyl -1,3,5- triazine |
| CN111039883A (en) * | 2020-01-21 | 2020-04-21 | 浙江工业大学 | Method for synthesizing triazine compound by Friedel-crafts reaction microchannel method |
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2021
- 2021-12-31 CN CN202111673475.3A patent/CN114230535A/en active Pending
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| CN107746389A (en) * | 2017-09-14 | 2018-03-02 | 江苏丹霞新材料有限公司 | The method that Fu Ke methods are prepared to the catalyst recycling in aryl s-triazine UV absorbers |
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