CN113582898A - Methylthio-diafenthiuron and preparation method thereof - Google Patents
Methylthio-diafenthiuron and preparation method thereof Download PDFInfo
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- CN113582898A CN113582898A CN202110990683.XA CN202110990683A CN113582898A CN 113582898 A CN113582898 A CN 113582898A CN 202110990683 A CN202110990683 A CN 202110990683A CN 113582898 A CN113582898 A CN 113582898A
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- diafenthiuron
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- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- -1 methylthio diafenthiuron Chemical compound 0.000 claims abstract description 69
- 239000000203 mixture Substances 0.000 claims abstract description 52
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 40
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000003960 organic solvent Substances 0.000 claims abstract description 29
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 20
- 238000001816 cooling Methods 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 238000002156 mixing Methods 0.000 claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- 239000012074 organic phase Substances 0.000 claims description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 238000003756 stirring Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- 239000000047 product Substances 0.000 description 20
- 230000000052 comparative effect Effects 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- KDRXVOFDHGLZKO-UHFFFAOYSA-N methyl n'-tert-butyl-n-[4-phenoxy-2,6-di(propan-2-yl)phenyl]carbamimidothioate Chemical compound C1=C(C(C)C)C(NC(SC)=NC(C)(C)C)=C(C(C)C)C=C1OC1=CC=CC=C1 KDRXVOFDHGLZKO-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/32—Isothioureas having sulfur atoms of isothiourea groups bound to acyclic carbon atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses methylthio diafenthiuron and a preparation method thereof, and belongs to the technical field of organic synthesis. The preparation method of the methylthio diafenthiuron comprises the following steps: s1, mixing an organic solvent, potassium carbonate and diafenthiuron to obtain a first mixture, and cooling the first mixture to 5-15 ℃; s2, dropwise adding dimethyl sulfate into the cooled first mixture, controlling the reaction temperature to be 5-25 ℃, and continuing to react for 1-2 hours after dropwise adding to obtain a mixture containing methylthio-diafenthiuron. The invention also discloses the methylthio diafenthiuron prepared by the preparation method. The prepared methylthio-diafenthiuron has high yield and high purity.
Description
Technical Field
The invention relates to the technical field of organic synthesis, and particularly relates to methylthio diafenthiuron and a preparation method thereof.
Background
Methylthio-diafenthiuron; chemical name: 1-tert-butyl-3- (2, 6-diisopropyl-4-phenoxyphenyl) -2-methylisothiourea has good insecticidal and acaricidal activity. The prior art also provides a method for preparing the methylthio diafenthiuron, and particularly, the methylthio diafenthiuron is prepared by a one-pot method of dichloromethane, potassium carbonate, diafenthiuron and dimethyl sulfate, and then the methylthio diafenthiuron is obtained by evaporating an organic solvent dichloromethane.
Disclosure of Invention
The invention aims to overcome the technical defects, provides the methylthio diafenthiuron and the preparation method thereof, and solves the technical problems of low yield and purity of the methylthio diafenthiuron prepared in the prior art.
In order to achieve the technical purpose, the technical scheme of the invention provides a preparation method of methylthio-diafenthiuron, which comprises the following steps:
s1, mixing an organic solvent, potassium carbonate and diafenthiuron to obtain a first mixture, and cooling the first mixture to 5-15 ℃;
s2, dropwise adding dimethyl sulfate into the cooled first mixture, controlling the reaction temperature to be 5-25 ℃, and continuing to react for 1-2 hours after dropwise adding to obtain a mixture containing methylthio-diafenthiuron.
Further, after the step S2, a step S3 is further included: adding water into the mixture containing the methylthio-diafenthiuron, stirring, standing for layering to obtain an organic phase, and removing the organic solvent in the organic phase to obtain the methylthio-diafenthiuron.
Further, in step S3, the water is added and stirred at 20-30 ℃.
Further, in step S3, the stirring time is 40 to 60 minutes.
Further, in step S1, the mass ratio of the organic solvent, the potassium carbonate and the diafenthiuron is (1.2-1.5): (0.3-0.8): (1-1.5).
Further, in step S2, the mass ratio of the dimethyl sulfate to the diafenthiuron is (0.33-0.4): 1-1.5.
Further, in step S3, the mass ratio of the water to the diafenthiuron is (2-2.5): (1-1.5).
Further, in step S3, the organic phase is distilled to remove the organic solvent in the organic phase.
Further, after the step S3, a step S4 is further included: and (4) purifying the methylthio diafenthiuron, specifically, adding methanol into the methylthio diafenthiuron obtained in the step S3, heating to dissolve the methyl alcohol, and then cooling, crystallizing, centrifuging and drying to obtain the methylthio diafenthiuron product.
In addition, the invention also provides the methylthio-diafenthiuron prepared by the preparation method.
Compared with the prior art, the invention has the beneficial effects that: the reaction of dimethyl sulfate and diafenthiuron is an exothermic reaction, firstly, an organic solvent, potassium carbonate and diafenthiuron are mixed to obtain a first mixture, the temperature of the first mixture is reduced to 5-15 ℃, dimethyl sulfate is dropwise added to react, the reaction temperature is controlled to be 5-25 ℃, the addition speed of dimethyl sulfate is controlled by dropwise adding dimethyl sulfate, the condition that the reaction temperature is overheated and the temperature is kept to be 5-25 ℃ is avoided, a byproduct is further avoided being generated by the reaction of dimethyl sulfate and diafenthiuron at a higher temperature, then, the reaction is continued for 1-2 hours to obtain a mixture containing methylthio diafenthiuron, the obtained mixture containing methylthio diafenthiuron has few byproducts, the yield of methylthio diafenthiuron is high, and the influence of the byproducts on the purity of methylthio diafenthiuron is avoided.
The method comprises the steps of adding water into a mixture containing the methylthio diafenthiuron, stirring the mixture to react to generate salt, allowing the salt to enter a water phase, allowing the methylthio diafenthiuron and a solvent to enter an organic phase, preliminarily removing the salt, removing the organic solvent in the organic phase to obtain the methylthio diafenthiuron, and removing the salt by removing the organic solvent and washing with water, wherein the product is thick and is not easy to disperse in water, so that the salt is not easy to remove, and the purity of the methylthio diafenthiuron is influenced.
Drawings
FIG. 1 is a high performance liquid chromatogram of methylthio-diafenthiuron prepared in example 1 of the present invention.
FIG. 2 is a high performance liquid chromatogram of methylthio-diafenthiuron prepared in comparative example 1 according to the invention.
Detailed Description
The specific embodiment provides a preparation method of methylthio diafenthiuron, which comprises the following steps:
s1, mixing an organic solvent, potassium carbonate and diafenthiuron to obtain a first mixture, and cooling the first mixture to 5-10 ℃; the mass ratio of the organic solvent, the potassium carbonate and the diafenthiuron is (1.2-1.5): (0.3-0.8): (1-1.5); the organic solvent is preferably dichloromethane;
s2, dropwise adding dimethyl sulfate into the cooled first mixture, controlling the reaction temperature to be 5-25 ℃, and continuously reacting for 1-2 hours after dropwise adding is finished to obtain a mixture containing methylthio-diafenthiuron; the mass ratio of the dimethyl sulfate to the diafenthiuron is (0.33-0.4) to (1-1.5);
s3, adding water into the mixture containing the methylthio-diafenthiuron according to the mass ratio (2-2.5) of the water to the diafenthiuron (1-1.5), stirring for 40-60 minutes at 20-30 ℃, standing and layering to obtain an organic phase, and distilling the organic phase to remove the organic solvent in the organic phase to obtain the methylthio-diafenthiuron;
s4, purifying the methylthio diafenthiuron, and specifically, adding methanol into the methylthio diafenthiuron, heating for dissolving, cooling, crystallizing, centrifuging and drying to obtain the methylthio diafenthiuron product.
The reaction equation for producing methylthio-diafenthiuron is as follows:
the specific embodiment also comprises the methylthio-diafenthiuron prepared by the preparation method.
In order to make the objects, technical solutions and advantages of the present invention more clearly understood, the following method will be further described in detail with reference to the accompanying drawings and examples. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
The embodiment provides a preparation method of methylthio-diafenthiuron, which comprises the following steps:
s1, mixing organic solvents of dichloromethane, potassium carbonate and diafenthiuron to obtain a first mixture, and cooling the first mixture to 5 ℃; the mass ratio of the organic solvent to the potassium carbonate to the diafenthiuron is 1.2:0.3: 1;
s2, dropwise adding dimethyl sulfate into the cooled first mixture, controlling the reaction temperature to be 5-25 ℃, and continuously reacting for 1 hour after dropwise adding is finished to obtain a mixture containing methylthio-diafenthiuron; the mass ratio of the dimethyl sulfate to the diafenthiuron is 0.33: 1;
s3, adding water into the mixture containing the methylthio-diafenthiuron according to the mass ratio of the water to the diafenthiuron of 2:1, stirring for 40 minutes at 30 ℃, standing and layering to obtain an organic phase, and distilling the organic phase to remove dichloromethane to obtain the methylthio-diafenthiuron;
s4, purifying methylthio diafenthiuron, specifically, adding methanol into the methylthio diafenthiuron, heating for dissolving, cooling, crystallizing, centrifuging and drying to obtain a methylthio diafenthiuron product, wherein the yield of the methylthio diafenthiuron product is 85.8%, the purity of the methylthio diafenthiuron product is 99.5%, and the prepared methylthio diafenthiuron contains almost no impurities as can be seen from a high performance liquid chromatogram of figure 1.
Example 2
The embodiment provides a preparation method of methylthio-diafenthiuron, which comprises the following steps:
s1, mixing organic solvents of dichloromethane, potassium carbonate and diafenthiuron to obtain a first mixture, and cooling the first mixture to 10 ℃; the mass ratio of the organic solvent to the potassium carbonate to the diafenthiuron is 1.5:0.8: 1.2;
s2, dropwise adding dimethyl sulfate into the cooled first mixture, controlling the reaction temperature to be 5-25 ℃, and continuously reacting for 2 hours after dropwise adding is finished to obtain a mixture containing methylthio-diafenthiuron; the mass ratio of the dimethyl sulfate to the diafenthiuron is 0.4: 1.5;
s3, adding water into the mixture containing the methylthio-diafenthiuron according to the mass ratio of 2.2:1.1 of the water to the diafenthiuron, stirring for 60 minutes at 20 ℃, standing for layering to obtain an organic phase, and distilling the organic phase to remove dichloromethane in the organic phase to obtain the methylthio-diafenthiuron;
s4, purifying the methylthio diafenthiuron, specifically, adding methanol into the methylthio diafenthiuron, heating for dissolving, cooling, crystallizing, centrifuging and drying to obtain the methylthio diafenthiuron product, wherein the yield of the methylthio diafenthiuron product is 85.1%, and the purity of the methylthio diafenthiuron product is 99.2%.
Example 3
The embodiment provides a preparation method of methylthio-diafenthiuron, which comprises the following steps:
s1, mixing organic solvents of dichloromethane, potassium carbonate and diafenthiuron to obtain a first mixture, and cooling the first mixture to 8 ℃; the mass ratio of the organic solvent to the potassium carbonate to the diafenthiuron is 1.4:0.5: 1.2;
s2, dropwise adding dimethyl sulfate into the cooled first mixture, controlling the reaction temperature to be 5-25 ℃, and continuously reacting for 1.5 hours after dropwise adding is finished to obtain a mixture containing methylthio-diafenthiuron; the mass ratio of the dimethyl sulfate to the diafenthiuron is 0.35: 1.2;
s3, adding water into the mixture containing the methylthio-diafenthiuron according to the mass ratio of 2.2:1.3 of the water to the diafenthiuron, stirring for 50 minutes at 30 ℃, standing for layering to obtain an organic phase, and distilling the organic phase to remove dichloromethane in the organic phase to obtain the methylthio-diafenthiuron;
s4, purifying the methylthio diafenthiuron, specifically, adding methanol into the methylthio diafenthiuron, heating for dissolving, cooling, crystallizing, centrifuging and drying to obtain the methylthio diafenthiuron product, wherein the yield of the methylthio diafenthiuron product is 84.9%, and the purity of the methylthio diafenthiuron product is 98.8%.
Example 4
The embodiment provides a preparation method of methylthio-diafenthiuron, which comprises the following steps:
s1, mixing organic solvents of dichloromethane, potassium carbonate and diafenthiuron to obtain a first mixture, and cooling the first mixture to 15 ℃; the mass ratio of the organic solvent to the potassium carbonate to the diafenthiuron is 1.3:0.5: 1;
s2, dropwise adding dimethyl sulfate into the cooled first mixture, controlling the reaction temperature to be 5-25 ℃, and continuously reacting for 1 hour after dropwise adding is finished to obtain a mixture containing methylthio-diafenthiuron; the mass ratio of the dimethyl sulfate to the diafenthiuron is 0.38: 1.2;
s3, adding water into the mixture containing the methylthio-diafenthiuron according to the mass ratio of 2.2:1.5 of the water to the diafenthiuron, stirring for 40 minutes at 30 ℃, standing for layering to obtain an organic phase, and distilling the organic phase to remove dichloromethane in the organic phase to obtain the methylthio-diafenthiuron;
s4, purifying the methylthio diafenthiuron, specifically, adding methanol into the methylthio diafenthiuron, heating for dissolving, cooling, crystallizing, centrifuging and drying to obtain the methylthio diafenthiuron product, wherein the yield of the methylthio diafenthiuron product is 85.2%, and the purity of the methylthio diafenthiuron product is 98.5%.
Comparative example 1
The comparative example provides a preparation method of methylthio diafenthiuron, which comprises the following steps:
s1, mixing and reacting organic solvents of dichloromethane, potassium carbonate, diafenthiuron and dimethyl sulfate for 1 hour according to the mass ratio of 1.2:0.3:1:0.33 to obtain a mixture containing methylthio-diafenthiuron;
s2, adding water into the mixture containing the methylthio-diafenthiuron according to the mass ratio of the water to the diafenthiuron of 2:1, stirring for 40 minutes at 30 ℃, standing and layering to obtain an organic phase, and distilling the organic phase to remove the organic solvent in the organic phase to obtain the methylthio-diafenthiuron;
s3, purifying the methylthio diafenthiuron, specifically, adding methanol into the methylthio diafenthiuron, heating for dissolving, cooling, crystallizing, centrifuging and drying to obtain the methylthio diafenthiuron product, wherein the yield of the methylthio diafenthiuron product is 55.8%, and the purity of the methylthio diafenthiuron product is 76.5%.
The reason why the product of this comparative example is low in yield and not high in purity is that a large amount of by-products are present, and it can be seen from the high performance liquid chromatogram of FIG. 2 that the product contains a large amount of impurities.
Comparative example 2
The comparative example provides a preparation method of methylthio-diafenthiuron, which comprises the following steps:
s1, mixing organic solvents of dichloromethane, potassium carbonate and diafenthiuron to obtain a first mixture, and cooling the first mixture to 5 ℃; the mass ratio of the organic solvent to the potassium carbonate to the diafenthiuron is 1.2:0.3: 1;
s2, dropwise adding dimethyl sulfate into the cooled first mixture, controlling the reaction temperature to be 5-25 ℃, and continuously reacting for 1 hour after dropwise adding is finished to obtain a mixture containing methylthio-diafenthiuron; the mass ratio of the dimethyl sulfate to the diafenthiuron is 0.33: 1;
s3, distilling the mixture containing the methylthio diafenthiuron to remove dichloromethane to obtain a methylthio diafenthiuron crude product, adding water to the methylthio diafenthiuron to wash and remove salts in the methylthio diafenthiuron crude product, finding that the material is sticky and cannot be well dispersed in water, wherein the purity of the obtained methylthio diafenthiuron is not high and only 75.6%, and the obtained methylthio diafenthiuron is easy to stick to walls in the centrifugal separation process to influence the yield, and the yield is 62.3%.
The above-described embodiments of the present invention should not be construed as limiting the scope of the present invention. Any other corresponding changes and modifications made according to the technical idea of the present invention should be included in the protection scope of the claims of the present invention.
Claims (10)
1. The preparation method of methylthio diafenthiuron is characterized by comprising the following steps:
s1, mixing an organic solvent, potassium carbonate and diafenthiuron to obtain a first mixture, and cooling the first mixture to 5-15 ℃;
s2, dropwise adding dimethyl sulfate into the cooled first mixture, controlling the reaction temperature to be 5-25 ℃, and continuing to react for 1-2 hours after dropwise adding to obtain a mixture containing methylthio-diafenthiuron.
2. The method for producing methylthio diafenthiuron according to claim 1, further comprising, after step S2, step S3: adding water into the mixture containing the methylthio-diafenthiuron, stirring, standing for layering to obtain an organic phase, and removing the organic solvent in the organic phase to obtain the methylthio-diafenthiuron.
3. The process for producing methylthio diafenthiuron according to claim 2, wherein in step S3, the water is added and stirred at 20 to 30 ℃.
4. The process for producing methylthio diafenthiuron according to claim 3, wherein the stirring time in step S3 is 40 to 60 minutes.
5. The method for producing methylthio diafenthiuron according to claim 1, wherein in step S1, the mass ratio of the organic solvent, the potassium carbonate and the diafenthiuron is (1.2-1.5): (0.3-0.8): (1-1.5).
6. The method for producing methylthio diafenthiuron according to claim 1, wherein in step S2, the mass ratio of the dimethyl sulfate to the diafenthiuron is (0.33-0.4): (1-1.5).
7. The method for producing methylthio diafenthiuron according to claim 2, wherein in step S3, the mass ratio of the water to the diafenthiuron is (2-2.5) to (1-1.5).
8. The process for producing methylthio diafenthiuron according to claim 2, wherein in step S3, the organic phase is distilled to remove the organic solvent from the organic phase.
9. The method for producing methylthio diafenthiuron according to claim 2, further comprising, after step S3, step S4: and (4) purifying the methylthio diafenthiuron, specifically, adding methanol into the methylthio diafenthiuron obtained in the step S3, heating to dissolve the methyl alcohol, and then cooling, crystallizing, centrifuging and drying to obtain the methylthio diafenthiuron product.
10. Methylthio-diafenthiuron produced by the process according to any one of claims 1 to 9.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4328247A (en) * | 1979-09-19 | 1982-05-04 | Ciba-Geigy Corporation | Phenoxyphenylisothioureas, production thereof and use thereof in pest control, and phenoxyphenylthioureas as intermediates for the production of the phenoxyphenylisothioureas and use thereof in pest control |
| CN105693581A (en) * | 2015-08-31 | 2016-06-22 | 海利尔药业集团股份有限公司 | Method for preparing methylmercaptodiafenthiuron |
| CN110396054A (en) * | 2019-07-31 | 2019-11-01 | 京博农化科技有限公司 | A kind of green synthesis method of kresoxim-methyl |
| CN111170836A (en) * | 2020-02-13 | 2020-05-19 | 浙江福纬电子材料有限公司 | Preparation method of pentaerythritol triallyl ether |
-
2021
- 2021-08-26 CN CN202110990683.XA patent/CN113582898A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4328247A (en) * | 1979-09-19 | 1982-05-04 | Ciba-Geigy Corporation | Phenoxyphenylisothioureas, production thereof and use thereof in pest control, and phenoxyphenylthioureas as intermediates for the production of the phenoxyphenylisothioureas and use thereof in pest control |
| CN105693581A (en) * | 2015-08-31 | 2016-06-22 | 海利尔药业集团股份有限公司 | Method for preparing methylmercaptodiafenthiuron |
| CN110396054A (en) * | 2019-07-31 | 2019-11-01 | 京博农化科技有限公司 | A kind of green synthesis method of kresoxim-methyl |
| CN111170836A (en) * | 2020-02-13 | 2020-05-19 | 浙江福纬电子材料有限公司 | Preparation method of pentaerythritol triallyl ether |
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