CN109776436B - Preparation method of triazole compound - Google Patents
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- CN109776436B CN109776436B CN201910195020.1A CN201910195020A CN109776436B CN 109776436 B CN109776436 B CN 109776436B CN 201910195020 A CN201910195020 A CN 201910195020A CN 109776436 B CN109776436 B CN 109776436B
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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Abstract
The invention discloses a preparation method of a triazole compound, which comprises the following synthetic route; the compound shown in formula III is used as a main raw material to carry out substitution reaction with the compound shown in formula IV under an alkaline condition, so as to synthesize the triazole compound shown in formula V. The method has the following advantages: simple operation, low cost, no pollution, high yield, environmental protection, and suitability for modern industrial production.
Description
Technical Field
The invention relates to a preparation method of triazole compounds.
Background
The triazole compound has bactericidal bioactivity, high activity, unique action mechanism and environment friendship, and has specific effect on diseases difficult to control, such as rice blast, downy mildew, gray mold, damping off and the like. The bactericidal composition is mainly used for preventing and controlling banded sclerotial blight, rust disease, early blight, leaf spot disease, scab and powdery mildew on crops such as fruit trees, vegetables, wheat, potatoes, beans, melons and the like, has excellent control effects, has good protection and treatment effects on various fungal diseases such as vegetables, melons and fruits and the like, has the characteristic of long lasting period, and has no cross resistance with other bactericides. The bactericide has the characteristics of no environmental pollution, no agricultural product pollution and no natural enemy killing, and is an ideal bactericide for preventing and treating crop resistant diseases such as citrus scab, alternaria leaf spot and the like in various countries at present.
The triazole compound is a systemic triazole fungicide with protection and treatment effects, can be absorbed by roots, stems and leaves, can be quickly conducted upwards in plant bodies, and has a good control effect on diseases caused by ascomycetes, basidiomycetes and imperfect fungi, particularly wheat take-all, powdery mildew, rust disease, root rot, rice bakanae disease and sigatoka.
Disclosure of Invention
The invention provides an improved preparation method of a triazole compound, which adopts a formula III as a main raw material to carry out substitution reaction with a formula IV under an alkaline condition to synthesize the triazole compound shown in a formula V. The product has high yield, high purity, no pollution, environmental protection and suitability for modern industrial production.
The invention adopts the following technical scheme:
a preparation method of a triazole compound shown in the following formula V is provided, and the reaction route is as follows:
wherein:
R1selected from F, Cl, Br, I, Ra-S(＝O)-O-，RbSO3-，-N+≡N，-NRcRdReOR-ORf；Ra、RbEach independently selected from-CH3，-CF3，-CF2H or phenyl; ra、RbMay be the same or different; rc、Rd、ReEach independently selected from hydrogen and C1-C6Alkyl, acyl, ester, dialkyl or amide groups, RfIs selected from C1-C6An alkyl group;
R2is selected from-OH, -ORg，-NRhRior-SRj；RgIs selected from C1-C6An alkyl group; rh、RiEach independently selected from hydrogen and C1-C6Alkyl, acyl, ester, dialkyl or amide groups, RjSelected from hydrogen, alkyl, ester or phenyl;
R3selected from H, -CORk，-CN，-SO2Rl，-SORm，-PORnR°Rp-NO, or-NO2；Rk、Rl、RmEach independently selected from hydrogen and C1-C6Alkyl, phenyl or heteroaryl; rn、R°、RpEach independently selected from hydrogen and C1-C6Alkyl, acyl, ester or dialkyl;
R4、R5each independently selected from H, -COOH, -COORq，-CN，-OH，-SH，-SRs，-NH2，-N+≡N，-S-S-Rtor-CORu；Rq、Rs、RtEach independently selected from C1-C6An alkyl group; r4、R5The same or different;
R6、R7、R8、R9、R10each independently selected from H, Cl, Br, F, I, -NO2，-ORv，-NH2，-N+N, heterocyclic substituents or-NH2；RvIs selected from C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl or unsaturated monocyclic hydrocarbyl, aromatic hydrocarbyl or aromatic hydrocarbyl substituents;
x is selected from H, Cl, Br, I, F, -ORw，-NRx，-SRy，-OCORzImidazolyl, an N-containing heterocycle, or a sulfur-containing heterocycle.
Further, said C of the present invention1-C6The alkyl group can be a straight chain alkyl group, a straight chain alkyl group or a cycloalkyl group; in particular, it may be chosen from methyl, ethyl, propyl, butyl, pentyl or hexyl.
In some embodiments of the invention, R1、R2Each independently selected from H, F, Cl, Br, I, -CN, -OCH3or-OCH2CH3；R3Selected from-OH and-OCH3or-OCH2CH3。
In some embodiments of the present invention, the compound represented by formula I is selected from methyl haloacetate, ethyl haloacetate, methyl 2-haloacetoacetate, ethyl 2-haloacetoacetate, dimethyl halomalonate, ethyl halomalonate, methyl cyanoacetate or ethyl cyanoacetate, methyl methoxyacetate, ethyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate.
In some embodiments of the invention, R4、R5Each independently selected from H, -COOH, -CN, -OH, -SH, -NH2or-N+≡N。
In some embodiments of the invention, R6、R7、R8、R9、R10Each independently selected from H, Cl, Br, F, I, -NO2，-NH2，-N+N, or-NH2(ii) a X is selected from H, Cl, Br, I or F.
In some embodiments of the invention, R1、X、R8、R10Each independently is Cl or F; r2is-ORg，RgIs selected from C1-C6An alkyl group; preferably, RgIs methyl, ethyl, propyl, butyl, pentyl or hexyl; r3、R4、R5、R6、R7、R9Each independently is H.
Further, the compound shown in the formula III is used as a main raw material to perform substitution reaction with the compound shown in the formula IV under the alkaline condition, so that the triazole compound shown in the formula V can be prepared. The alkali is preferably any one or a combination of several of sodium hydrogen, triethylamine, N-dimethylaniline, DBU, diisopropylethylamine, sodium methoxide, sodium ethoxide, potassium methoxide, sodium tert-butoxide and potassium tert-butoxide.
Specifically, the preparation method of the triazole compound shown in the formula V comprises the following steps:
1) preparation of a compound of formula III:
stirring and mixing the compound shown in the formula II, an acid-binding agent and a solvent at a certain temperature, slowly dropwise adding the compound shown in the formula I, carrying out heat preservation reaction, and recovering the solvent.
Preferably, the compound represented by the formula I is selected from any one of methyl haloacetate, ethyl haloacetate, methyl 2-haloacetoacetate, ethyl 2-haloacetoacetate, dimethyl halomalonate, ethyl halomalonate, methyl cyanoacetate, ethyl cyanoacetate and the like.
Preferably, the acid-binding agent is any one or a combination of more of potassium carbonate, potassium hydroxide, sodium carbonate, potassium bicarbonate, sodium bicarbonate, DBU (1, 8-diazabicycloundecen-7-ene), triethylamine, N-dimethylaniline and diisopropylethylamine, and preferably is potassium carbonate. Researches find that the reaction rate can be remarkably improved by using the acid-binding agent.
Preferably, the solvent is methanol, acetonitrile, toluene or DMF (N, N-dimethylformamide), more preferably acetonitrile. Research finds that the reaction selectivity can be remarkably improved by using the solvent.
Preferably, the stirring and mixing temperature is 0-30 ℃;
preferably, the temperature of the heat preservation reaction is 0-120 ℃, and more preferably 0-30 ℃; studies have found that by-product production can be significantly reduced at this preferred temperature.
Preferably, the incubation reaction time is 6 to 12 hours, more preferably 8 to 10 hours.
Preferably, the molar ratio of the compound shown in the formula II to the compound shown in the formula I to the acid binding agent is 1 (1.1-2): (1.1-2), more preferably 1 (1.1-1.5): (1.1-1.5);
2) preparation of a Compound of formula V:
stirring and mixing a compound shown as a formula III, alkali and a solvent at a certain temperature, slowly dropwise adding a compound shown as a formula IV dissolved in the solvent under the protection of nitrogen, carrying out heat preservation reaction, adding water, standing for layering, recovering an organic phase, and removing the solvent to obtain the compound shown as the formula III;
preferably, the solvent is any one or more of toluene, THF (tetrahydrofuran), methyltetrahydrofuran, benzene, DMF, DMAC, dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, cyclohexane and xylene. The research finds that the reaction yield can be obviously improved by selecting the solvents.
Preferably, the base is any one or a combination of several of sodium hydrogen, triethylamine, N-dimethylaniline, DBU, diisopropylethylamine, sodium methoxide, sodium ethoxide, potassium methoxide, sodium tert-butoxide and potassium tert-butoxide, and more preferably sodium hydrogen or triethylamine.
Preferably, the stirring and mixing temperature and the heat preservation reaction temperature are respectively-15 to 20 ℃, and more preferably 5 to 10 ℃;
preferably, the reaction time is 1-6h, more preferably 2-4 h;
preferably, the molar ratio of the compound shown in the formula III to the compound shown in the formula IV to the base is 1 (1.0-1.5) to (3-5), and more preferably 1 (1.1-1.2) to (2.5-3).
The invention has the following advantages:
1) the acid-binding agent, the alkali and the solvent are easy to recycle and reuse;
2) the method has the advantages of simple operation, low cost, high yield and low requirement on equipment;
3) no pollution, environmental protection, and suitability for modern industrial production.
Detailed Description
The following examples further illustrate the embodiments of the present invention in detail. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The following reagents were purchased from carbofuran technologies, Inc.
The overall yields in the following examples are obtained according to the following formula:
yield of the compound represented by formula III ═ (mass of the compound represented by formula III × content of the compound represented by formula III × 100%)/(molar mass of the structural compound represented by formula II × molar mass of the structural compound represented by formula III)
The yield of the compound of the formula v ═ (mass of the compound of the formula v × content of the compound of the formula v × 100%)/(molar mass of the structural compound of the formula iii × molar mass of the structural compound of the formula v)
The purity of the compound of formula III in the following examples was determined by gas chromatography; the purity of the structural compound of formula V was determined by liquid chromatography.
Example 1
Adding 1.0mol of a compound shown as the following formula II into a 500ml four-mouth bottle, adding 240ml of toluene, adding 1.1mol of an acid-binding agent sodium carbonate, stirring at the temperature of 90 ℃, slowly dropwise adding 1.1mol of a compound shown as the following formula I (a Sea reagent, 98%), keeping the temperature for reacting for 6 hours, detecting the content of the compound to be less than 1% by using a gas chromatographic analyzer, filtering the solid after the reaction is finished, and recovering the toluene solvent to obtain 119.5 of a compound shown as the following formula III. The yield is 80.4% by calculation; the purity of the pure product is 95.0 percent through detection.
The reaction route is as follows:
wherein R is1Is Cl; r2is-OCH3；R3、R4、R5Each independently is H.
Example 2
Adding 1.0mol (141.1g) of a compound shown in the following formula III into a 1000ml four-mouth bottle, adding 400g of THF solvent (98%), slowly adding 3.0mol of sodium hydrogen at 5 ℃, reacting for 2h, then adding 1.1mol of a compound shown in the following formula IV, continuing to react for 2h, detecting that the content of the compound is less than 1% by using a gas chromatography analyzer, adding 200g of water when the reaction is finished, stirring for 30min, standing for layering, desolventizing an organic phase at normal pressure, and recovering THF; 299.8g of a compound represented by the following formula V was obtained. The calculated yield is 94%; the purity of the pure product is 98.5 percent through detection.
The reaction route is as follows:
wherein R is2is-OCH3；R3、R4、R5、R6、R7、R9Each independently is H; x, R8、R10Each independently Cl.
In this example, the compound of formula III can be prepared as in example 1.
Example 3
Adding 1.0mol (141.1g) of a compound shown in the following formula III into a 1000ml four-neck bottle, adding 400g of a methyl tetrahydrofuran solvent (98%), slowly dropwise adding 3.0mol of sodium hydrogen at 5 ℃, reacting for 2h, adding 1.1mol of a compound shown in the following formula IV, continuing to react for 2h, measuring the content of the compound to be less than 1% by using a gas chromatography analyzer, adding 200g of water when the reaction is finished, stirring for 30min, standing for layering, desolventizing an organic phase at normal pressure, and recovering the methyl tetrahydrofuran; 254.8g of a compound represented by the following formula V was obtained. The yield is 88.8% by calculation; the purity of the pure product is 98.0 percent through detection.
The reaction route is as follows:
wherein R is2is-OCH3；R3、R4、R5、R6、R7、R9Each independently is H; x is Cl;
R8、R10each independently is F.
In this example, the compound of formula III can be prepared as in example 1.
Example 4
The only difference from example 2 was that sodium hydrogen was replaced with an equal amount of DBU to give 180.4g of the compound of formula V. The yield is 57.4 percent by calculation; the purity of the pure product is 98.0 percent through detection.
Example 5
The only difference from example 2 was that 3.0mol of sodium hydrogen was slowly added dropwise at 30 ℃ to obtain 240.5g of the compound represented by the formula V. The yield is 75.0 percent by calculation; the purity of the pure product is 98.0 percent through detection.
Example 6
Substantially as described in examples 1 and 2, R in the compound of formula I2Replacement by-ORgWherein R isgEthyl, propyl, butyl, pentyl or hexyl, respectively, to prepare the compound of formula V.
Example 7
Substantially as described in examples 1 and 3, R in the compound of formula I2Replacement by-ORgWherein R isgEthyl, propyl, butyl, pentyl or hexyl, respectively, to prepare the compound of formula V.
The preferred embodiments of the present invention have been described above in detail, but the present invention is not limited thereto. Within the scope of the technical idea of the invention, many simple modifications can be made to the technical solution of the invention, including combinations of various technical features in any other suitable manner and including the sequence of combinations, and these simple modifications and combinations should also be regarded as the disclosure of the invention, and all fall within the scope of the invention.
Claims (18)
1. The preparation method of the triazole compound shown in the formula V is characterized in that the reaction route is as follows,
wherein:
R1selected from Cl, Br, I;
R2is selected from-OH, -ORg，-SRj；RgIs selected from C1-C6An alkyl group; rjSelected from hydrogen, C1-C6An alkyl group;
R3is selected from H;
R4、R5each independently selected from H;
R6、R7、R8、R9、R10each independently selected from H, Cl, Br, F, I;
x is selected from Cl;
wherein, the compound of formula III and the compound of formula IV are subjected to substitution reaction under alkaline condition to synthesize the triazole compound shown in formula V; the alkali is sodium hydrogen; the reaction temperature is 5-10 ℃.
2. The method according to claim 1, wherein C is1-C6Alkyl is straight chain alkyl.
3. The method according to claim 1, wherein C is1-C6Alkyl radicalSelected from methyl, ethyl, propyl, butyl, pentyl or hexyl.
4. The method of claim 1, wherein R is1Selected from Cl, Br, I; r2Is selected from-OCH3、-OCH2CH3。
5. The preparation method according to claim 1, wherein the compound represented by formula I is selected from halogenated methyl acetate and halogenated ethyl acetate, and the halogen generation is Cl generation, Br generation or I generation.
6. The method of claim 1, wherein R is1Selected from Cl; r2Is selected from-OCH3；R3、R4、R5Each independently is H.
7. The method of claim 1, wherein R is6、R7、R8、R9、R10Each independently selected from H; x is Cl.
8. The method of claim 1, wherein R is1、X、R8、R10Each independently is Cl or F; r2is-ORg，RgIs selected from C1-C6An alkyl group; r3、R4、R5、R6、R7、R9Each independently is H.
9. The method of claim 8, wherein R isgIs methyl, ethyl, propyl, butyl, pentyl or hexyl.
10. The method of claim 1, wherein R is1Selected from Cl; r2Is selected from-OCH3；R3、R4、R5、R6、R7、R9Each independently is H; x, R8、R10Each independently Cl.
11. The method of claim 1, wherein R is1Selected from Cl; r2Is selected from-OCH3；R3、R4、R5、R6、R7、R9Each independently is H; x is Cl; r8、R10Each independently is F.
12. The method of any one of claims 1 to 11, comprising the steps of:
1) stirring and mixing the compound shown in the formula II, an acid-binding agent and a solvent at a certain temperature, slowly dropwise adding the compound shown in the formula I, carrying out heat preservation reaction, and recovering the solvent to obtain a compound shown in the formula III;
2) stirring and mixing the compound shown in the formula III, alkali and a solvent at a certain temperature, slowly dropwise adding the compound shown in the formula IV dissolved in the solvent under the protection of nitrogen, keeping the temperature for reaction, adding water for standing and layering, recovering an organic phase, and removing the solvent to obtain the compound shown in the formula V.
13. The preparation method of claim 12, wherein the acid-binding agent in step 1) is any one or a combination of potassium carbonate, potassium hydroxide, sodium carbonate, potassium bicarbonate, sodium bicarbonate, DBU, triethylamine, N-dimethylaniline and diisopropylethylamine; and/or the solvent is methanol, acetonitrile, toluene or DMF;
the solvent in the step 2) is any one or more of toluene, THF, methyltetrahydrofuran, benzene, DMF, DMAC, dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, cyclohexane and xylene.
14. The preparation method of claim 12, wherein the molar ratio of the compound of formula II, the compound of formula I and the acid-binding agent in step 1) is 1 (1.1-2): (1.1-2); and/or the presence of a gas in the gas,
the molar ratio of the compound shown in the formula III to the compound shown in the formula IV to the alkali in the step 2) is 1 (1.0-1.5) to 3-5.
15. The preparation method of claim 12, wherein the molar ratio of the compound of formula II, the compound of formula I and the acid-binding agent in step 1) is 1 (1.1-1.5) to (1.1-1.5); and/or the presence of a gas in the gas,
the molar ratio of the compound shown in the formula III to the compound shown in the formula IV to the alkali in the step 2) is 1 (1.1-1.2) to 2.5-3.
16. The method according to claim 12, wherein the incubation reaction temperature in step 1) is 0 to 120 ℃; and/or, the temperature of the heat preservation reaction in the step 2) is-15 to 20 ℃.
17. The method according to claim 12, wherein the incubation reaction temperature in step 1) is 0 to 30 ℃; and/or, the reaction temperature of the heat preservation in the step 2) is 5-10 ℃.
18. The method according to claim 12, wherein the incubation temperature in step 2) is 5 ℃.
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| PCT/CN2019/086613 WO2020181646A1 (en) | 2019-03-14 | 2019-05-13 | Method for preparing triazole compounds |
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| CN111978302B (en) * | 2019-05-24 | 2022-03-22 | 帕潘纳(北京)科技有限公司 | Triazole cyanide compound and preparation method thereof |
| CN112552248A (en) * | 2019-09-10 | 2021-03-26 | 帕潘纳(北京)科技有限公司 | Preparation method of imidazole and triazole compound intermediate |
Citations (2)
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| EP0209738A1 (en) * | 1985-07-15 | 1987-01-28 | Chemie Linz Aktiengesellschaft | Benzoyl-triazolyl-acetic-acid or -thio-acetic-acid derivatives, their production and biocidal agents containing them |
| CN103958500A (en) * | 2011-10-10 | 2014-07-30 | 奥赖恩公司 | Protein kinase inhibitors |
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| AU6016696A (en) * | 1996-06-14 | 1998-01-07 | Toyama Chemical Co. Ltd. | Process for producing 2-(1h-1,2,4-triazol-1-yl)acetophenones |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0209738A1 (en) * | 1985-07-15 | 1987-01-28 | Chemie Linz Aktiengesellschaft | Benzoyl-triazolyl-acetic-acid or -thio-acetic-acid derivatives, their production and biocidal agents containing them |
| CN103958500A (en) * | 2011-10-10 | 2014-07-30 | 奥赖恩公司 | Protein kinase inhibitors |
Non-Patent Citations (2)
| Title |
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| Antimycobacterial activities of novel 2-(sub)-3-fluoro/nitro-5, 12-dihydro-5-oxobenzothiazolo[3,2-a]quinoline-6-carboxylic acid;Murugesan Dinakaran等;《Bioorganic & Medicinal Chemistry》;20071109;第16卷(第6期);第3414页方案1 * |
| Synthesis of new 1,2,4-triazolylmethylthiadiazolylazetidines as antimicrobial, anticonvulsant and ntiinflammatory agents;S.K.Srivastava等;《Indian Journal of Chemistry》;20021130;第41B卷(第11期);第2358页方案I * |
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Denomination of invention: Preparation of a triazole compound Effective date of registration: 20210702 Granted publication date: 20201218 Pledgee: Agricultural Development Bank of China Baiyin branch business department Pledgor: Purpana (Beijing) Technologies Co.,Ltd. Registration number: Y2021990000573 |