CN104876873A - Synthetic method of enilconazole - Google Patents
Synthetic method of enilconazole Download PDFInfo
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- CN104876873A CN104876873A CN201510267728.5A CN201510267728A CN104876873A CN 104876873 A CN104876873 A CN 104876873A CN 201510267728 A CN201510267728 A CN 201510267728A CN 104876873 A CN104876873 A CN 104876873A
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- enilconazole
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- synthetic method
- dichlorophenyl
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- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 239000005795 Imazalil Substances 0.000 title claims abstract description 24
- 229960002125 enilconazole Drugs 0.000 title claims abstract description 24
- 238000010189 synthetic method Methods 0.000 title claims abstract description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 41
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012043 crude product Substances 0.000 claims abstract description 11
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 239000000047 product Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims description 12
- 150000002460 imidazoles Chemical class 0.000 claims description 9
- JIJGKPVJAALUQQ-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)ethanol Chemical compound OCCC1=CC=C(Cl)C=C1Cl JIJGKPVJAALUQQ-UHFFFAOYSA-N 0.000 claims description 8
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- XHEPANNURIQWRM-UHFFFAOYSA-N 2-chloro-1-(2,4-dichlorophenyl)ethanol Chemical compound ClCC(O)C1=CC=C(Cl)C=C1Cl XHEPANNURIQWRM-UHFFFAOYSA-N 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 5
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- 238000001816 cooling Methods 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- 238000010792 warming Methods 0.000 abstract 2
- 238000001035 drying Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 240000008790 Musa x paradisiaca Species 0.000 description 2
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- SQFWQHCKCDSOJK-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)ethanol Chemical compound CC(O)C1=NC=CN1 SQFWQHCKCDSOJK-UHFFFAOYSA-N 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241000675108 Citrus tangerina Species 0.000 description 1
- 244000241257 Cucumis melo Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000220225 Malus Species 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 239000006013 carbendazim Substances 0.000 description 1
- JNPZQRQPIHJYNM-UHFFFAOYSA-N carbendazim Chemical compound C1=C[CH]C2=NC(NC(=O)OC)=NC2=C1 JNPZQRQPIHJYNM-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 238000012803 optimization experiment Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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
- C07D233/60—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 hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a synthetic method of enilconazole. The method comprises the following steps: adding DMF, imidazole and caustic soda flakes into a reaction vessel, uniformly stirring and blending the materials; slowly heating the materials till the temperature reaches 110-115 DEG C and keeping the temperature for 1 hour; cooling the materials till the temperature drops to 50-55 DEG C; dripping a DMF solution of 2-chlorine-1-(2, 4'-dichlorophenyl)-ethyl alcohol into the materials, controlling the temperature at 50-55 DEG C, keeping the temperature for 1 hour after dripping the solution, warming the materials till the temperature reaches 110-115 DEG C, and keeping the temperature for 4 hours; adding caustic soda flakes and dripping chloropropene into the materials, controlling the temperature at 50-55 DEG C, keeping the temperature for 1 hour, warming the materials till the temperature reaches 110-115 DEG C, and keeping the temperature for reaction for 3 hours; adding water and cooling the materials to room temperature; carrying out centrifugal filtration to obtain a crude product of the enilconazole; drying the crude product, and recrystallizing the dried crude product with methylbenzene to obtain a dried product. The method is simple in device, simplified in steps, low in production cost, and applicable to industrial production.
Description
Technical field
The present invention relates to organic synthesis field, particularly relate to a kind of synthetic method of enilconazole.
Background technology
Enilconazole: 1-[2-(2,4 dichloro benzene base)-2-(allyloxy) ethyl]-1H-imidazoles, has another name called imazalil, IMAZALIL, prepares the raw material of antifungal drug and fruit antistaling agent.For preventing and treating oranges and tangerines, mango, banana, apple, the crop pest such as melon, also can be used for control cereal crop disease, having special efficacy to the penicillium of resisting carbendazim, thiabendazole.Enilconazole can be prepared into systemic fungicide, has preventive effect to many fungal diseases of invasion and attack fruit, vegetables and ornamental plant.Formula dipping is sprayed to citrus, banana and other fruit, the water after results can be prevented and treated and rot; Animal doctor is upper mainly as local antibacterial medicine.
Summary of the invention
The object of this invention is to provide a kind of synthetic method of enilconazole, equipment is simple, easy to operate, is applicable to industrial production.
In technical solutions according to the invention, use high polar solvent DMF (dimethyl formamide), PEG600 is catalyzer.In the chemical reaction of the technical program, reactive behavior increases along with the polarity of solvent and increases, and is on the one hand because the solubleness of substrate, catalyzer and solvent increase the extraction efficiency of ion pair Q+Y-; Be in dipole organic solvent, form dipole-dipole key with solvent based on the halohydrocarbon with moment of dipole on the other hand, between the ion pair Q+Y-that non-nucleophilic anion is combined with catalyst cation and solvent, also have this effect.In theory, at the temperature of 50 DEG C-55 DEG C, be applicable temperature of reaction, but the yield of product is low, is not easy to be separated; In specific experiment operation, grope to find by experiment repeatedly, react 110 DEG C-115 DEG C time, keep certain hour, yield significantly improves, and is easily separated.Contrast by experiment, optimization experiment step, make the yield of reaction the highest.
The object of the invention is to be achieved through the following technical solutions:
DMF, imidazoles, sheet alkali are joined in reaction vessel, is uniformly mixed, slowly heat to 110 DEG C-115 DEG C, be incubated 1 hour, cool to 50 DEG C-55 DEG C afterwards; Drip the DMF solution of 2-chloro-1-(2,4 '-dichlorophenyl)-ethanol, dropping limit, limit is stirred, and during dropping, temperature controls at 50 DEG C-55 DEG C, drips after terminating, is incubated 1 hour, is warmed up to 110 DEG C-115 DEG C, react after 4 hours, be cooled to 60 DEG C; Continue to drop into sheet alkali in reaction unit, keep 60 DEG C of temperature, stir 1 hour, drip propenyl chloride, dropping limit, limit is stirred, and temperature controls at 50 DEG C-55 DEG C, drips and terminates, be incubated 1 hour, be warmed up to 110 DEG C-115 DEG C afterwards, keep thermotonus 3 hours, add water, continue to be cooled to room temperature.Centrifuging, obtains the crude product of enilconazole; Crude product is dried, and obtains dry product with re crystallization from toluene.
Synthetic route is as follows:
The advantage of the synthetic method of the present invention's enilconazole used:
1, present method is being reacted by the chloro-1-of 2-(2,4 '-dichlorophenyl)-ethanol and imidazoles, after synthesis imidazolyl ethanol, directly adds propenyl chloride, and suitably add sheet alkali, direct reaction, generate enilconazole, realize " one pot goes out ", the equipment used is simple, and step simplifies, and is applicable to industrial production.
2, use DMF to do organic solvent in present method, respond and terminate after, can recycling, reduce production cost.
3, present method synthesis enilconazole, yield is high, and purity is high.
Embodiment
Below in conjunction with specific embodiment, the invention will be further described:
Embodiment 1
Take the chloro-1-of 2-(2,4 '-dichlorophenyl)-ethanol 23g to join in 20mL DMF, be uniformly mixed, the DMF solution of the obtained chloro-1-of 2-(2,4 '-dichlorophenyl)-ethanol;
Get DMF:80mL, imidazoles: 8.2g, sheet alkali: 8g, PEG600:1.8g put in four-hole boiling flask, access agitator, thermometer, condensing reflux pipe, stir, and heating, is slowly warmed up to 110 DEG C-115 DEG C, is incubated 1 hour, cools to 50 DEG C-55 DEG C; Drip the DMF solution of 2-chloro-1-(2,4 '-dichlorophenyl)-ethanol, dropping limit, limit is stirred, temperature controls at 50 DEG C-55 DEG C, drips and terminates, be incubated 1 hour, be warmed up to 110 DEG C-115 DEG C afterwards, keep thermotonus 4 hours, after reaction terminates, be cooled to 60 DEG C; Continue to drop into sheet alkali 8g in reaction unit, keep 60 DEG C of temperature, stir 1 hour, drip propenyl chloride 9g, dropping limit, limit is stirred, and temperature controls at 50 DEG C-55 DEG C, and drip and terminate, be incubated 4 hours, add water 200ml, continues to be cooled to room temperature.Centrifuging, obtains the crude product of enilconazole;
Dried by crude product, be weighed as 105g, with re crystallization from toluene, obtain dry product, be weighed as 97g, yield is 41%.
Embodiment 2
Take the chloro-1-of 2-(2,4 '-dichlorophenyl)-ethanol 23g to join in 20mL DMF, be uniformly mixed, the DMF mixed solution of the obtained chloro-1-of 2-(2.4 '-dichlorophenyl)-ethanol;
Get DMF:80mL, imidazoles: 8.2g, sheet alkali: 8g, PEG600:1.8g put in four-hole boiling flask, access agitator, thermometer, condensing reflux pipe, stir, and heating, is slowly warmed up to 110 DEG C-115 DEG C, is incubated 1 hour, cools to 50 DEG C-55 DEG C; Drip the DMF solution of 2-chloro-1-(2,4 '-dichlorophenyl)-ethanol, dropping limit, limit is stirred, temperature controls at 50 DEG C-55 DEG C, drips and terminates, be incubated 1 hour, be warmed up to 110 DEG C-115 DEG C afterwards, keep thermotonus 4 hours, after reaction terminates, be cooled to 60 DEG C; Continue to drop into sheet alkali 8g in reaction unit, keep 60 DEG C of temperature, stir 1 hour, drip propenyl chloride 9g, dropping limit, limit is stirred, temperature controls at 50 DEG C-55 DEG C, drips and terminates, be incubated 1 hour, be warmed up to 110 DEG C-115 DEG C afterwards, keep thermotonus 3 hours, add water 200ml, continues to be cooled to room temperature.Centrifuging, obtains the crude product of enilconazole;
Dried by crude product, be weighed as 215g, with re crystallization from toluene, obtain dry product, be weighed as 206g, yield is 87%.
Claims (6)
1. a synthetic method for enilconazole, is characterized in that, described enilconazole is by the chloro-1-(2 of 2-, 4 '-dichlorophenyl)-ethanol, imidazoles, propenyl chloride in DMF solvent, in the presence of a base, use PEG600 make catalyzer, reaction generates, and synthesis step comprises following:
(1) prepare the DMF solution of the chloro-1-of 2-(2,4 '-dichlorophenyl)-ethanol, be uniformly mixed;
(2) take DMF, imidazoles, sheet alkali, PEG600 respectively, drop in reaction unit, stir, be slowly warmed up to 110 DEG C-115 DEG C, be incubated 1 hour, cool to 50 DEG C-55 DEG C;
(3) drip the DMF solution of 2-chloro-1-(2,4 '-dichlorophenyl)-ethanol, dropping limit, limit is stirred, and temperature controls at 50 DEG C-55 DEG C, drip and terminate, be incubated 1 hour, be warmed up to 110 DEG C-115 DEG C afterwards, keep thermotonus 4 hours, after reaction terminates, be cooled to 60 DEG C;
(4) continue to drop into sheet alkali in reaction unit, keep 60 DEG C of temperature, stir 1 hour;
(5) drip propenyl chloride, dropping limit, limit is stirred, and temperature controls at 50 DEG C-55 DEG C, drips and terminates, be incubated 1 hour, be warmed up to 110 DEG C-115 DEG C afterwards, keeps thermotonus 3 hours, adds water, continue to be cooled to room temperature; Centrifuging, obtains the crude product of product enilconazole;
(6) dried by crude product, re crystallization from toluene, obtains dry product.
2. the synthetic method of enilconazole according to claim 1, is characterized in that the chloro-1-of described 2-(2,4 '-dichlorophenyl)-ethanol, the mol ratio of imidazoles is 1:1.2.
3. the synthetic method of enilconazole according to claim 1, is characterized in that the mass ratio of the chloro-1-of 2-(2,4 '-dichlorophenyl)-ethanol, DMF in described step (1) is 1:1.
4. the synthetic method of enilconazole according to claim 1, is characterized in that the mol ratio of imidazoles, sheet alkali, PEG600 in described step (2) is 1.2:2:0.03.
5. the synthetic method of enilconazole according to claim 1, is characterized in that the add-on of sheet alkali described in described step (4) is identical with the sheet alkali add-on in step (2).
6. the synthetic method of enilconazole according to claim 1, the mol ratio that it is characterized in that dripping described in described step (5) the imidazoles input amount in the amount of propenyl chloride and step (2) is 1:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510267728.5A CN104876873A (en) | 2015-05-22 | 2015-05-22 | Synthetic method of enilconazole |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510267728.5A CN104876873A (en) | 2015-05-22 | 2015-05-22 | Synthetic method of enilconazole |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110437154A (en) * | 2019-09-10 | 2019-11-12 | 武汉川泰科技有限公司 | A kind of preparation method of enilconazole bulk pharmaceutical chemicals |
| CN110845416A (en) * | 2019-11-19 | 2020-02-28 | 武汉回盛生物科技股份有限公司 | O-allylation method of α -diaryl substituted ethanol |
| CN115433132A (en) * | 2022-10-20 | 2022-12-06 | 武汉回盛生物科技股份有限公司 | A kind of enconazole crystal form, preparation method and application |
| CN116606255A (en) * | 2023-05-18 | 2023-08-18 | 上海农帆生物科技有限公司 | Preparation method of imazalil |
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2015
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110437154A (en) * | 2019-09-10 | 2019-11-12 | 武汉川泰科技有限公司 | A kind of preparation method of enilconazole bulk pharmaceutical chemicals |
| CN110845416A (en) * | 2019-11-19 | 2020-02-28 | 武汉回盛生物科技股份有限公司 | O-allylation method of α -diaryl substituted ethanol |
| CN115433132A (en) * | 2022-10-20 | 2022-12-06 | 武汉回盛生物科技股份有限公司 | A kind of enconazole crystal form, preparation method and application |
| CN116606255A (en) * | 2023-05-18 | 2023-08-18 | 上海农帆生物科技有限公司 | Preparation method of imazalil |
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Application publication date: 20150902 |