CN105111148A - 2-[(N-para-chlorophenyl)-3-pyrazole oxymethyl]nitrobenzene and preparation method therefor and application thereof - Google Patents
2-[(N-para-chlorophenyl)-3-pyrazole oxymethyl]nitrobenzene and preparation method therefor and application thereof Download PDFInfo
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- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The present invention discloses a 2-[(N-para-chlorophenyl)-3-pyrazole oxymethyl]nitrobenzene and a preparation method therefor and an application thereof. The method comprises the specific steps of: (1) mixing 1-(4-chlorophenyl)-3-pyrazolone, a solvent and a catalyst uniformly, raising temperature and introducing air to perform a reaction, and adding water to perform distillation; (2) lowering the temperature of the above distillate to room temperature, adding a small amount of water, then adding simultaneously 12% NaOH solution and o-nitro bromobenzyl chlorobenzene solution dropwise; (3) after a completion of the reaction in step (2), adding a little hydrochloric acid dropwise, adjusting pH value, then adding water to desolventize, lowering the temperature to 8-12 DEG C after the completion of the desolvention, performing a suction filtration to obtain 2-[(N-para-chlorophenyl)-3-pyrazole oxymethyl]nitrobenzene. According to the process, purity of the obtained product is over 95.0%, product quality is good, yield is around 76.0%, and the yield is high and totally suitable for industrial mass production.
Description
Technical field
The invention belongs to fine chemistry industry to produce and technical field of pesticide, particularly relate to the preparation method of a kind of 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane, also relate to the application of 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane.
Background technology
Pyraclostrobin Pyraclostrobin has another name called Strobilurin, is a kind of methoxy methyl acrylate class wide-spectrum bactericide having pyrrazole structure concurrently that BASF Aktiengesellschaft found in 1993.Molecular formula C
19h
18clN
3o
4, its structural formula is:
This sterilant fungicidal spectrum is wide, has efficient, low toxicity, to features such as non-target organism safety and environmental friendliness, is widely used.The preparation method of current 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane is prepared with 1-(4-chloro-phenyl-)-3-pyrazoles alcohol and adjacent nitro bromobenzyl chlorobenzene liquid; this process not only produces a large amount of waste water; operate more complicated; cost is higher; the purity of 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane is more than 95.0% simultaneously; yield is about 70%, cannot meet the large-scale production requirement of existing factory.
Chinese invention patent (publication number is CN104496905A) discloses the preparation method of a kind of 2-[(N-4-chloro-phenyl-)-3-pyrazoles oxygen ylmethyl] oil of mirbane, the method with 1-(4-chloro-phenyl-)-3-pyrazoles alcohol and adjacent nitrobenzyl bromine for raw material, the mixed solvent formed with water and organic solvent is for action solvent, react under alkaline reagents and phase-transfer catalyst effect, after completion of the reaction, cooling suction filtration, can obtain product after oven dry.Problems existing is, situ production is carried out by the method, cannot reach in the specification sheets of this disclosure of the invention content >=98% recording 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane, yield >=90%, every data even only have about 70% at all.
Summary of the invention
Problem to be solved by this invention is to provide a kind of efficient, economic, green, safety and meets the preparation method of 2-[(N-the rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane of industrialization production requirements, adopt one kettle way with 1-(4-chloro-phenyl-)-3-pyrazolone and adjacent nitro bromobenzyl chlorobenzene liquid for raw material, 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane is obtained through oxidation, condensation reaction, simple to operate, cost is lower, waste water reduces, environmentally friendly, yield and purity high.
The preparation method of a kind of 2-of the present invention [(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane, concrete steps are:
(1) oxidizing reaction: be 1:3 ~ 4:0.05 ~ 0.075 Homogeneous phase mixing in mass ratio by 1-(4-chloro-phenyl-)-3-pyrazolone, solvent and catalyzer, be warming up to 50 ~ 65 DEG C, pass into air reaction 5 ~ 7h, after reaction terminates, add water distillation, steamed completely by solvent;
(2) condensation reaction: above-mentioned distillate temperature is down to 55 ~ 70 DEG C, adds little water, then drips 12%NaoH solution and adjacent nitro bromobenzyl chlorobenzene liquid jointly, controls temperature of reaction at 55 ~ 70 DEG C, ensures certain time for adding;
(3) after step (2) reaction terminates, drip a little hydrochloric acid, regulate PH to 6.5 ~ 7.5, then add water precipitation, cool to 8 ~ 12 DEG C after solvent has taken off, suction filtration obtains 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane.
Preferably, the preparation method of the adjacent nitro bromobenzyl chlorobenzene liquid in described step (1) is: be that 1:2.5 ~ 3.0:1.5 ~ 2:1.0 ~ 1.5:0.035 ~ 0.04 mixes by the mass ratio of chlorobenzene, Hydrogen bromide, Ortho Nitro Toluene, hydrogen peroxide and initiator, at 65 ~ 70 DEG C, react 4 ~ 6h.
Preferably, the catalyzer in described step (1) is FeCl
3, a kind of in CuCl or their mixture.
Preferably, the solvent in described step (1) is one or more the mixture in o-Xylol, toluene, DMF, p-Xylol.
Preferably, the reaction times in described step (2) is 2 ~ 3h.
Preferably, the common time for adding of dropping of the NaoH solution in described step (2) and adjacent nitro bromobenzyl chlorobenzene liquid is 1 ~ 1.5h, and Ortho Nitro Toluene rate of addition is 20 ~ 25d/min, NaOH rate of addition is 15 ~ 20d/min.
Preferably, 1-(4-the chloro-phenyl-)-3-pyrazolone in described step (2): NaOH solution: the mass ratio of adjacent nitro bromobenzyl chlorobenzene liquid is 1:3.5 ~ 5.5:4.5 ~ 5.5.
Preferably, described initiator is one or more the mixture in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), azo-bis-iso-dimethyl, di-t-butyl peroxide.
Another object of the present invention is to provide the application as pyraclostrobin intermediate of 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane that a kind of aforesaid method obtains and this product.
The invention has the beneficial effects as follows:
1) 1-(4-chloro-phenyl-)-3-pyrazolone is the raw material of 1-(4-chloro-phenyl-)-3-pyrazoles alcohol, 1-(4-chloro-phenyl-)-3-pyrazolone obtains 1-(4-chloro-phenyl-)-3-pyrazoles alcohol through peroxidation, and adopt this technique can obtain 1-(4-chloro-phenyl-)-3-pyrazoles alcohol product, direct generation target product, eliminate middle loaded down with trivial details technique, shorten reaction time, improve production efficiency.
2) product purity that this technique obtains is more than 95.0%, good product quality, and yield is about 76.0%, and yield is high, is applicable to plant sizeization completely and produces.
3) compared with the prior art, synthesis 1t product waste water reduces about 3t, decreases the discharge of the three wastes, meets the requirement of green chemistry process, have good industrial application value.
Embodiment
Below by example, the present invention is described, but the present invention is not limited to these embodiments.
Embodiment 1
100g1-(4-chloro-phenyl-)-3-pyrazolone, 300gN is added, dinethylformamide and 5gFeCl in reaction kit
3, be warmed up to 65 DEG C, pass into air reaction 7h, after reaction terminates, add water distillation, steamed completely by solvent.
Above-mentioned distillate is cooled to 55 DEG C, add a small amount of water, then 350g12%NaoH solution and 450g adjacent nitro bromobenzyl chlorobenzene liquid is dripped, Ortho Nitro Toluene rate of addition is 20d/min, NaOH rate of addition is 15d/min, time for adding is 1.5h, controls temperature of reaction at 55 DEG C, reaction 2.5h, after reaction terminates, drip a little hydrochloric acid, regulate PH to neutral, then add water precipitation, about 10 DEG C are cooled to after solvent has taken off, suction filtration obtains 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane solid, and dry, yield is 76.8%.
The preparation method of adjacent nitro bromobenzyl chlorobenzene liquid: add 760g chlorobenzene, 506g Hydrogen bromide, 253g Ortho Nitro Toluene, 379.5 hydrogen peroxide and 8.85 Diisopropyl azodicarboxylate hybrid reactions in reaction kit, react 5h at 70 DEG C.
Embodiment 2
100g1-(4-chloro-phenyl-)-3-pyrazolone, 300g toluene and 5gFeCl is added in reaction kit
3, be warmed up to 65 DEG C and pass into air reaction 7h, after reaction terminates, add water distillation, steamed completely by solvent.
Above-mentioned distillate is cooled to 55 DEG C, add a small amount of water, then 350g12%NaoH solution and 450g adjacent nitro bromobenzyl chlorobenzene liquid is dripped, Ortho Nitro Toluene rate of addition is 20d/min, NaOH rate of addition is 15d/min, time for adding is 1.5h, controls temperature of reaction at 55 DEG C, reaction 2.5h, after reaction terminates, drip a little hydrochloric acid, regulate PH to neutral, then add water precipitation, about 10 DEG C are cooled to after solvent has taken off, suction filtration obtains 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane solid, and dry, yield is 79.3%.
The preparation method of adjacent nitro bromobenzyl chlorobenzene liquid: add 760g chlorobenzene, 506g Hydrogen bromide, 253g Ortho Nitro Toluene, 379.5 hydrogen peroxide and 8.85 Diisopropyl azodicarboxylate hybrid reactions in reaction kit, react 5h at 65 DEG C.
Embodiment 3
100g1-(4-chloro-phenyl-)-3-pyrazolone is added, 400g o-Xylol and 7.5gFeCl in reaction kit
3, be warmed up to 60 DEG C and pass into air reaction 7h, after reaction terminates, add water distillation, steamed completely by solvent.
Above-mentioned distillate is cooled to 70 DEG C, add a small amount of water, then 550g12%NaoH solution and 450g adjacent nitro bromobenzyl chlorobenzene liquid is dripped, Ortho Nitro Toluene rate of addition is 25d/min, NaOH rate of addition is 20d/min, time for adding is 1h, controls temperature of reaction at 70 DEG C, reaction 2.5h, after reaction terminates, drip a little hydrochloric acid, regulate PH to neutral, then add water precipitation, about 10 DEG C are cooled to after solvent has taken off, suction filtration obtains 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane solid, and dry, yield is 77.3%.
The preparation method of adjacent nitro bromobenzyl chlorobenzene liquid: add 632.5g chlorobenzene, 379.5g Hydrogen bromide, 253g Ortho Nitro Toluene, 379.5 hydrogen peroxide and 8.85 Diisopropyl azodicarboxylate hybrid reactions in reaction kit, react 5h at 68 DEG C.
Embodiment 4
In reaction kit, add 100g1-(4-chloro-phenyl-)-3-pyrazolone, 400g o-Xylol and 7.5gCuCl, be warmed up to 60 DEG C and pass into air reaction 7h, after reaction terminates, add water distillation, steamed completely by solvent.
Above-mentioned distillate is cooled to 70 DEG C, add a small amount of water, then 550g12%NaoH solution and 450g adjacent nitro bromobenzyl chlorobenzene liquid is dripped, Ortho Nitro Toluene rate of addition is 25d/min, NaOH rate of addition is 20d/min, time for adding is 1h, controls temperature of reaction at 70 DEG C, reaction 2.5h, after reaction terminates, drip a little hydrochloric acid, regulate PH to neutral, then add water precipitation, about 10 DEG C are cooled to after solvent has taken off, suction filtration obtains 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane solid, and dry, yield is 76.8%.
The preparation method of adjacent nitro bromobenzyl chlorobenzene liquid: add 632.5g chlorobenzene, 379.5g Hydrogen bromide, 253g Ortho Nitro Toluene, 379.5 hydrogen peroxide and 8.85 Diisopropyl azodicarboxylate hybrid reactions in reaction kit, react 5h at 68 DEG C.
Embodiment 5
In reaction kit, add 100g1-(4-chloro-phenyl-)-3-pyrazolone, 300gN, dinethylformamide and 5gCuCl, be warmed up to 65 DEG C, passes into air reaction 7h, and after reaction terminates, add water distillation, steamed completely by solvent.
Above-mentioned distillate is cooled to 55 DEG C, add a small amount of water, then 350g12%NaoH solution and 450g adjacent nitro bromobenzyl chlorobenzene liquid is dripped, Ortho Nitro Toluene rate of addition is 25d/min, NaOH rate of addition is 20d/min, time for adding is 1.5h, controls temperature of reaction at 55 DEG C, reaction 2.5h, after reaction terminates, drip a little hydrochloric acid, regulate PH to neutral, then add water precipitation, about 10 DEG C are cooled to after solvent has taken off, suction filtration obtains 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane solid, and dry, yield is 75.8%.
The preparation method of adjacent nitro bromobenzyl chlorobenzene liquid: add 760g chlorobenzene, 506g Hydrogen bromide, 253g Ortho Nitro Toluene, 379.5 hydrogen peroxide and 8.85 Diisopropyl azodicarboxylate hybrid reactions in reaction kit, react 5h at 65 DEG C.
Embodiment 6
In reaction kit, add 100g1-(4-chloro-phenyl-)-3-pyrazolone, 300g toluene and 5gCuCl, be warmed up to 60 DEG C and pass into air reaction 6h, after reaction terminates, add water distillation, steamed completely by solvent.
Above-mentioned distillate is cooled to 60 DEG C, add a small amount of water, then 350g12%NaoH solution and 450g adjacent nitro bromobenzyl chlorobenzene liquid is dripped, Ortho Nitro Toluene rate of addition is 25d/min, NaOH rate of addition is 20d/min, time for adding is 1.5h, controls temperature of reaction at 60 DEG C, reaction 2.5h, after reaction terminates, drip a little hydrochloric acid, regulate PH to neutral, then add water precipitation, about 10 DEG C are cooled to after solvent has taken off, suction filtration obtains 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane solid, and dry, yield is 76.4%.
The preparation method of adjacent nitro bromobenzyl chlorobenzene liquid: add 760g chlorobenzene, 506g Hydrogen bromide, 253g Ortho Nitro Toluene, 379.5 hydrogen peroxide and 8.85 Diisopropyl azodicarboxylate hybrid reactions in reaction kit, react 5h at 70 DEG C.
From above three tables, data can draw, add reaction promoter in reaction process, the transformation efficiency of pyridine raw material brings up to more than 95%, and the productive rate of 2,2'-dipyridyl brings up to about 76%, are applicable to plant sizeization completely and produce.
Claims (10)
1. a preparation method for 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane, it is characterized in that, concrete steps are:
(1) oxidizing reaction: be 1:3 ~ 4:0.05 ~ 0.075 Homogeneous phase mixing in mass ratio by 1-(4-chloro-phenyl-)-3-pyrazolone, solvent and catalyzer, be warming up to 50 ~ 65 DEG C, pass into air reaction 5 ~ 7h, after reaction terminates, add water distillation, steamed completely by solvent;
(2) condensation reaction: above-mentioned distillate temperature is down to 55 ~ 70 DEG C, adds little water, then drips 12%NaoH solution and adjacent nitro bromobenzyl chlorobenzene liquid jointly, controls temperature of reaction at 55 ~ 70 DEG C, ensures certain time for adding;
(3) after step (2) reaction terminates, drip a little hydrochloric acid, regulate PH to 6.5 ~ 7.5, then add water precipitation, cool to 8 ~ 12 DEG C after solvent has taken off, suction filtration obtains 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane.
2. preparation method according to claim 1, it is characterized in that, the preparation method of the adjacent nitro bromobenzyl chlorobenzene liquid in described step (1) is: be that 1:2.5 ~ 3.0:1.5 ~ 2:1.0 ~ 1.5:0.035 ~ 0.04 mixes by the mass ratio of chlorobenzene, Hydrogen bromide, Ortho Nitro Toluene, hydrogen peroxide and initiator, at 65 ~ 70 DEG C, react 4 ~ 6h.
3. preparation method according to claim 1, is characterized in that, the catalyzer in described step (1) is FeCl
3, a kind of in CuCl or their mixture.
4. preparation method according to claim 1, is characterized in that, the solvent in described step (1) is one or more the mixture in o-Xylol, toluene, DMF, p-Xylol.
5. preparation method according to claim 1, is characterized in that, the reaction times in described step (2) is 2 ~ 3h.
6. preparation method according to claim 1, it is characterized in that, the common time for adding of dropping of the NaoH solution in described step (2) and adjacent nitro bromobenzyl chlorobenzene liquid is 1 ~ 1.5h, Ortho Nitro Toluene rate of addition is 20 ~ 25d/min, NaOH rate of addition is 15 ~ 20d/min.
7. preparation method according to claim 1, is characterized in that, 1-(4-the chloro-phenyl-)-3-pyrazolone in described step (2): NaOH solution: the mass ratio of adjacent nitro bromobenzyl chlorobenzene liquid is 1:3.5 ~ 5.5:4.5 ~ 5.5.
8. preparation method according to claim 1, is characterized in that, described initiator is one or more the mixture in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), azo-bis-iso-dimethyl, di-t-butyl peroxide.
9. 2-[(N-the rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane that the preparation method according to any one of claim 1 to 8 obtains.
10. according to claim 9 2-[(N-rubigan)-3-pyrazoles oxygen ylmethyl] oil of mirbane as the application of pyraclostrobin intermediate.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693611A (en) * | 2016-04-26 | 2016-06-22 | 江苏托球农化股份有限公司 | Green synthesis technology for 3-(2-nitrobenzene methoxy)-1-(4-chlorphenyl)-1H-pyrazole |
| CN105837508A (en) * | 2016-05-06 | 2016-08-10 | 江西金元莱高新材料有限公司 | Crystallizing and purifying process of pyraclostrobin condensation intermediates |
| CN106008350A (en) * | 2016-07-21 | 2016-10-12 | 山东益丰生化环保股份有限公司 | Preparation method of 1-(4-chlorophenyl)-3-pyrazole alcohol |
| CN106928145A (en) * | 2017-04-17 | 2017-07-07 | 安徽广信农化股份有限公司 | A kind of synthesis system of pyraclostrobin Intermediate nitro benzene |
| CN106946785A (en) * | 2017-04-17 | 2017-07-14 | 安徽广信农化股份有限公司 | A kind of synthesis technique of pyraclostrobin intermediate pyrazole alcohol |
| CN108218779A (en) * | 2017-12-23 | 2018-06-29 | 杨向党 | Do not purify directly make 2-（N-4- chlorphenyls）- 3- pyrazoles oxygroups methyl } nitrobenzene |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693611A (en) * | 2016-04-26 | 2016-06-22 | 江苏托球农化股份有限公司 | Green synthesis technology for 3-(2-nitrobenzene methoxy)-1-(4-chlorphenyl)-1H-pyrazole |
| CN105837508A (en) * | 2016-05-06 | 2016-08-10 | 江西金元莱高新材料有限公司 | Crystallizing and purifying process of pyraclostrobin condensation intermediates |
| CN106008350A (en) * | 2016-07-21 | 2016-10-12 | 山东益丰生化环保股份有限公司 | Preparation method of 1-(4-chlorophenyl)-3-pyrazole alcohol |
| CN106928145A (en) * | 2017-04-17 | 2017-07-07 | 安徽广信农化股份有限公司 | A kind of synthesis system of pyraclostrobin Intermediate nitro benzene |
| CN106946785A (en) * | 2017-04-17 | 2017-07-14 | 安徽广信农化股份有限公司 | A kind of synthesis technique of pyraclostrobin intermediate pyrazole alcohol |
| CN108218779A (en) * | 2017-12-23 | 2018-06-29 | 杨向党 | Do not purify directly make 2-（N-4- chlorphenyls）- 3- pyrazoles oxygroups methyl } nitrobenzene |
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