CN118373754B - Clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide - Google Patents
Clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide Download PDFInfo
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- CN118373754B CN118373754B CN202410806532.8A CN202410806532A CN118373754B CN 118373754 B CN118373754 B CN 118373754B CN 202410806532 A CN202410806532 A CN 202410806532A CN 118373754 B CN118373754 B CN 118373754B
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- methyl
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- methoxyiminobenzyl
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- PSOUEYMPCQDWAH-UHFFFAOYSA-N n-methoxy-2-methylbenzenecarboximidoyl cyanide Chemical compound CON=C(C#N)C1=CC=CC=C1C PSOUEYMPCQDWAH-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000001308 synthesis method Methods 0.000 title claims abstract description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 51
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- BLLFVUPNHCTMSV-UHFFFAOYSA-N methyl nitrite Chemical compound CON=O BLLFVUPNHCTMSV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000000047 product Substances 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 8
- WMGVPDQNPUQRND-UHFFFAOYSA-N (2-methylphenyl)acetonitrile Chemical compound CC1=CC=CC=C1CC#N WMGVPDQNPUQRND-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000706 filtrate Substances 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 5
- 238000004321 preservation Methods 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 3
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000011084 recovery Methods 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 230000035484 reaction time Effects 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005800 Kresoxim-methyl Substances 0.000 description 3
- 239000005857 Trifloxystrobin Substances 0.000 description 3
- ZOTBXTZVPHCKPN-HTXNQAPBSA-N kresoxim-methyl Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1COC1=CC=CC=C1C ZOTBXTZVPHCKPN-HTXNQAPBSA-N 0.000 description 3
- -1 nitrous acid ester Chemical class 0.000 description 3
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 238000010612 desalination reaction Methods 0.000 description 2
- 238000011033 desalting Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- LQAQMOIBXDELJX-UHFFFAOYSA-N 2-methoxyprop-2-enoic acid Chemical compound COC(=C)C(O)=O LQAQMOIBXDELJX-UHFFFAOYSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- QQZWEECEMNQSTG-UHFFFAOYSA-N Ethyl nitrite Chemical compound CCON=O QQZWEECEMNQSTG-UHFFFAOYSA-N 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention is applicable to the technical field of organic synthesis, and provides a clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide, which comprises the following steps: adding o-methyl benzyl cyanide, alkali and methanol into a reactor, heating to a certain temperature, introducing methyl nitrite gas, dropwise adding dimethyl sulfate, and then carrying out heat preservation reaction for 0.5-1h after the addition; after the reaction is finished, cooling to room temperature, filtering to remove salt, concentrating filtrate to recover solvent, and distilling under reduced pressure to obtain the target product 2-methyl-alpha-methoxyiminobenzyl cyanide. According to the invention, o-methyl benzyl cyanide is used as a raw material, a double-adding mode is adopted, methyl nitrite gas is introduced, and dimethyl sulfate is simultaneously added dropwise, so that the separation and purification of an intermediate are not needed, the reaction time is greatly shortened, the efficiency is greatly improved, methanol is used as a solvent, the recovery is convenient, the reaction yield is not influenced, the post-treatment is simple, the process is simple and smooth, and the method is suitable for industrial production.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide.
Background
The trifloxystrobin and the kresoxim-methyl are high-efficiency and safe methoxy acrylic acid ester bactericides, have the characteristics of high efficiency, low toxicity, wide bactericidal spectrum and the like, are effective on powdery mildew, leaf spot, rust, downy mildew, apple scab and the like, and the 2-methyl-alpha-methoxyiminobenzyl cyanide is a key intermediate for synthesizing the trifloxystrobin and the kresoxim-methyl.
Patent application publication No. CN108863845A discloses that o-methyl benzyl cyanide and tert-butyl nitrite react at 60 ℃ under alkaline condition, then are subjected to post-treatment such as decompression, methanol removal, hydrochloric acid acidification, ethyl acetate extraction, drying, desolventizing and the like, dimethyl sulfate is dropwise added under alkaline condition and lower than 10 ℃, and the post-treatment operations such as reaction completion filtration, rotary evaporation, ethyl acetate dissolution and the like are finished, wherein various solvents are adopted, the solvents are difficult to recover, the intermediate is related to operations such as separation and purification, and the reaction flow is too complex.
Zhu Xiaomeng [ Shandong university's Shuoshi paper, 2013] is to condense o-methylbenzonitrile and ethyl nitrite under alkaline condition, after post-treatment, change solvent DMF and react with dimethyl sulfate under alkaline condition to obtain target product, wherein a one-pot reaction of ethanol as solvent is disclosed, but methyl sulfate methylation can generate methanol byproduct, rectification separation and recovery of methanol and ethanol are involved, oximation and methylation are separately carried out, reaction time is long, efficiency is low, and the post-treatment also involves ethyl acetate extraction operation, so that flow is too complex.
Patent application with publication number CN110396054A discloses that o-methyl benzyl cyanide is taken as a raw material, nitrous acid ester is added under the condition of an organic solvent and alkali, oxime salt is obtained after the reaction is finished and filtered, and then the oxime salt is dried; or hydrochloric acid is added into the system and then suction filtration is carried out to obtain an intermediate, and then the intermediate reacts with dimethyl sulfate under alkaline conditions to obtain a target product.
Therefore, a method for preparing the 2-methyl-alpha-methoxyiminobenzyl cyanide serving as an intermediate of trifloxystrobin and kresoxim-methyl suitable for industrial scale-up production is sought, which has a great significance.
Disclosure of Invention
The embodiment of the invention aims to provide a clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide, which aims to solve the problems in the background technology.
The embodiment of the invention is realized in such a way that the synthetic route of the clean synthetic method of the 2-methyl-alpha-methoxyiminobenzyl cyanide is as follows:
；
The method comprises the following steps:
S1: adding o-methyl benzyl cyanide, alkali and methanol into a reactor, heating to a certain temperature, introducing methyl nitrite gas, dropwise adding dimethyl sulfate, and then carrying out heat preservation reaction for 0.5-1h after the addition;
S2: after the reaction is finished, cooling to room temperature, filtering to remove salt, concentrating filtrate to recover solvent, and distilling under reduced pressure to obtain the target product 2-methyl-alpha-methoxyiminobenzyl cyanide.
Preferably, the alkali is one or more of sodium hydroxide, potassium hydroxide, sodium methoxide, sodium carbonate and potassium carbonate.
Preferably, the base is sodium hydroxide or potassium hydroxide.
Preferably, the o-methylbenzonitrile: methyl nitrite: alkali: the molar ratio of the dimethyl sulfate is 1:1.0-3.0:1.0-3.0:1.0-2.0.
Preferably, the o-methylbenzonitrile: methyl nitrite: alkali: the molar ratio of the dimethyl sulfate is 1:1.0-2.0:1.0-2.0:1.0-1.5.
Preferably, in the step of heating to a temperature, the temperature is in the range of 0-80 ℃.
Preferably, in the step of heating to a temperature, the temperature is 50-60 ℃.
According to the clean synthesis method of the 2-methyl-alpha-methoxyiminobenzyl cyanide, which is provided by the embodiment of the invention, o-methyl benzyl cyanide is used as a raw material, a double-adding mode is adopted, methyl nitrite gas is introduced, dimethyl sulfate is simultaneously added dropwise, separation and purification of an intermediate are not needed, the reaction time is greatly shortened, the efficiency is greatly improved, methanol is used as a solvent, the recovery is convenient, the reaction yield is not influenced, and the post-treatment is simple; the reaction is carried out by adopting a one-pot method, the reaction time is greatly shortened, the efficiency is greatly improved, the raw materials are cheap and easy to obtain, the reaction condition is mild, the process is simple and smooth, and the method is suitable for industrial production.
Detailed Description
The present invention will be described in further detail with reference to the following examples in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
Specific implementations of the invention are described in detail below in connection with specific embodiments.
Example 1
A clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide comprises the following steps:
In a three-neck flask, adding 100.0g of methanol, 50.0g of o-methylbenzonitrile and 22.9g of sodium hydroxide, stirring and heating to 50-60 ℃, simultaneously dropwise adding 72.1g of dimethyl sulfate while introducing 34.9g of methyl nitrite gas, keeping the temperature for 0.5-1h after adding, cooling to room temperature, filtering and desalting, concentrating filtrate to recover methanol, and then distilling under reduced pressure to obtain 65.5g of product with the purity of 96.6% and the yield of 95.3%.
Example 2
A clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide comprises the following steps:
in a three-neck flask, adding 100.0g of methanol, 50.0g of o-methylbenzonitrile and 32.1g of potassium hydroxide, stirring and heating to 50-60 ℃, simultaneously dropwise adding 72.1g of dimethyl sulfate while introducing 34.9g of methyl nitrite gas, keeping the temperature for 0.5-1h after adding, cooling to room temperature, filtering and desalting, concentrating filtrate to recover methanol, and then distilling under reduced pressure to obtain 66.1g of product with the purity of 96.3% and the yield of 95.8%.
Example 3
A clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide comprises the following steps:
In a three-neck flask, 100.0g of the recovery solvent methanol, 50.0g of o-methylbenzonitrile and 22.9g of sodium hydroxide are added, stirred and heated to 50-60 ℃, 34.9g of methyl nitrite gas is introduced, 72.1g of dimethyl sulfate is simultaneously added dropwise, the temperature is kept for 0.5-1h after the addition, the temperature is reduced to room temperature, the filtration and the desalination are carried out, the filtrate is concentrated and the methanol is recovered, and then the product is obtained through reduced pressure distillation, wherein the purity is 96.2%, and the yield is 95.6%.
Example 4
A clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide comprises the following steps:
In a three-neck flask, 100.0g of the recovery solvent methanol, 50.0g of o-methylbenzonitrile and 32.1g of potassium hydroxide are added, stirred and heated to 50-60 ℃, 34.9g of methyl nitrite gas is introduced, 72.1g of dimethyl sulfate is simultaneously added dropwise, the temperature is kept for 0.5-1h after the addition, the temperature is reduced to room temperature, the filtration and the desalination are carried out, the filtrate is concentrated and the methanol is recovered, and then the product with 65.6g of purity and 96.7 percent of yield of 95.5 percent is obtained through reduced pressure distillation.
In summary, the solvent methanol recovered by concentration in the embodiment of the invention can be directly recovered without complex high-energy-consumption treatment processes such as rectification and the like, and meanwhile, the yield is not influenced, the energy consumption is greatly reduced, and the production efficiency is improved.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, and alternatives falling within the spirit and principles of the invention.
Claims (2)
1.A clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide is characterized by comprising the following synthesis routes:
；
The method comprises the following steps:
S1: adding o-methyl benzyl cyanide, alkali and methanol into a reactor, heating to a certain temperature, introducing methyl nitrite gas, dropwise adding dimethyl sulfate, and then carrying out heat preservation reaction for 0.5-1h after the addition, wherein the alkali is sodium hydroxide or potassium hydroxide;
s2: after the reaction is finished, cooling to room temperature, filtering to remove salt, concentrating filtrate to recover solvent, and distilling under reduced pressure to obtain a target product 2-methyl-alpha-methoxyiminobenzyl cyanide;
The o-methylbenzonitrile: methyl nitrite: alkali: the molar ratio of the dimethyl sulfate is 1:1.0-3.0:1.0-3.0:1.0-2.0, and heating to a certain temperature, wherein the temperature is 50-60 ℃.
2. The clean synthesis method of 2-methyl- α -methoxyiminobenzyl cyanide according to claim 1, wherein the o-methylbenzonitrile: methyl nitrite: alkali: the molar ratio of the dimethyl sulfate is 1:1.0-2.0:1.0-2.0:1.0-1.5.
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| CN202410806532.8A CN118373754B (en) | 2024-06-21 | 2024-06-21 | Clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide |
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| CN202410806532.8A CN118373754B (en) | 2024-06-21 | 2024-06-21 | Clean synthesis method of 2-methyl-alpha-methoxyiminobenzyl cyanide |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108863845A (en) * | 2018-08-21 | 2018-11-23 | 湖南大学 | A kind of preparation method of trifloxystrobin and its intermediate |
| CN220835498U (en) * | 2023-09-26 | 2024-04-26 | 湖北省祥珈科技有限公司 | Device for continuously synthesizing 2-methyl-alpha-hydroxy iminobenzyl cyanide sodium salt |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110396054B (en) * | 2019-07-31 | 2022-09-20 | 京博农化科技有限公司 | Green synthesis method of kresoxim-methyl |
| CN112851546B (en) * | 2019-11-12 | 2023-10-03 | 江西天宇化工有限公司 | Preparation method of (E) -2-methyl-alpha-methoxyiminophenylacetic acid methyl ester and intermediate thereof |
| CN113912513B (en) * | 2021-11-19 | 2024-01-26 | 青岛恒宁生物科技有限公司 | Preparation method of oximido acetate compound and intermediate thereof |
| CN115417793A (en) * | 2022-09-20 | 2022-12-02 | 山东华升新材料有限公司 | Method for preparing (E) -2-methyl-alpha-methoxyimino methyl phenylacetate |
| CN115925578A (en) * | 2022-12-21 | 2023-04-07 | 辽宁众辉生物科技有限公司 | Novel synthesis method of trifloxystrobin intermediate |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108863845A (en) * | 2018-08-21 | 2018-11-23 | 湖南大学 | A kind of preparation method of trifloxystrobin and its intermediate |
| CN220835498U (en) * | 2023-09-26 | 2024-04-26 | 湖北省祥珈科技有限公司 | Device for continuously synthesizing 2-methyl-alpha-hydroxy iminobenzyl cyanide sodium salt |
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