CN1051906A - The preparation method of metaxanin - Google Patents
The preparation method of metaxanin Download PDFInfo
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- CN1051906A CN1051906A CN 89107346 CN89107346A CN1051906A CN 1051906 A CN1051906 A CN 1051906A CN 89107346 CN89107346 CN 89107346 CN 89107346 A CN89107346 A CN 89107346A CN 1051906 A CN1051906 A CN 1051906A
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Abstract
Metaxanin is a disinfectant use in agriculture, and structural formula is:
Make behind the methoxyacetic acid sodium without the direct chloride of acidifying by Mono Chloro Acetic Acid or sodium chloroacetate and sodium methylate, intermediate product methoxyacetic acid sodium and methoxyacetyl chloride are without separating, make methoxylation, chloride and amidate action successively react the method for producing metaxanin in same reactor.
Description
The invention belongs to the preparation method of disinfectant use in agriculture.
The chemical name of metaxanin is N-(2, the 6-xylyl)-N-(2-methoxy ethanoyl-racemize-alanine methyl esters, structural formula is:
Up to the present, the synthetic method of reporting this medicament abroad is to adopt N-(2, the 6-xylyl)-alanine methyl esters and methoxyacetyl chloride generation chloride after again amidate action make.U.s.4,317,916(1982) the thick yield of report product is 97.2%.Methoxyacetyl chloride is wherein made by methoxyacetic acid sodium or methoxyacetic acid usually.Brit.ukPat，APP1。GB2,085,429(1982) method of middle report manufacturing methoxyacetyl chloride is that Mono Chloro Acetic Acid and sodium methylate effect make methoxyacetic acid sodium, this sodium salt obtains methoxyacetyl chloride with the phosgene effect in the presence of dimethyl formamide.Ger, Offen, 2,832,947(1979) middle report: methoxyacetic acid sodium is through acidifying, and extraction makes methoxyacetic acid, and perhaps 2-methyl cellosolve makes methoxyacetic acid with nitric acid oxidation, and then makes with chlorides such as thionyl chloride, Benzoyl chlorides.
Above-mentioned reported method all is the substep preparation, and operational path is long, and operating performance is numerous and diverse, and the intermediate yield is lower, and how the three wastes are difficult for is again handled, and is difficult to push to produce.Propose in the CN85106327 patent of the court's application: by N-(2, the 6-3,5-dimethylphenyl) the patent characteristics of alanine methyl esters Metalaxyl synthesizing are that methoxyacetic acid sodium that Mono Chloro Acetic Acid or sodium chloroacetate and sodium methylate make is without acidifying, directly with chlorination of phosphorus oxychloride, intermediate product methoxyacetic acid sodium and methoxyacetyl chloride are without separating, make methoxylation, chloride and amidation are carried out in a reactor, thereby have simplified technology greatly, improve yield and reduce quantity of three wastes.But it just does acyl chlorinating agent with phosphorus oxychloride.
The objective of the invention is to propose a kind of processing method, it is to carry out in same reactor under chloride and the amidated situation, enlarges acyl chlorinating agent raw material use range.
The present invention adopts all acyl chlorinating agents to prepare methoxyacetyl chloride, and the one-step synthesis metaxanin of going forward side by side is all succeedd, and selected best acyl chlorinating agent also has phosphorus trichloride, phosphorus pentachloride, sulfur oxychloride, phosgene etc. except that phosphorus oxychloride.Its synthetic technological condition is: the methoxyacetic acid sodium that Mono Chloro Acetic Acid or sodium chloroacetate and sodium methylate make is without acidifying, directly with the acyl chlorinating agent chloride, intermediate product methoxyacetic acid sodium and methoxyacetyl chloride are without separating, make methoxylation, chloride and amidation are carried out the prepared in reaction metaxanin in a reactor.Proportioning raw materials: N-(2, the 6-3,5-dimethylphenyl) the alanine methyl esters: Mono Chloro Acetic Acid: sodium methylate: acyl chlorinating agent=1.0: 1.05～1.4: 2.1～2.8: 0.4～0.6; Methoxyacetic acid sodium synthesis temperature is 30 °～70 ℃, 0.5～2 hour reaction times; The methoxyacetyl chloride synthesis temperature is 30～110 ℃, and the reaction times is 0.5～3.0 hour; The metaxanin temperature of reaction is 30～110 ℃, and the reaction times is 0.5～4.0 hour.
Synthetic example one
0.25 molar Mono Chloro Acetic Acid adding is had in the there-necked flask of agitator, thermometer, reflux exchanger and dropping funnel, add 20 milliliters of methyl alcohol.Start stirring, treat Mono Chloro Acetic Acid all after the dissolving, dripping 0.5 mol content from dropping funnel is 28～30% sodium methoxide solution.Heating was also reacted 1 hour under reflux temperature, heating steams 70～75% of methyl alcohol total amount then, add each 200 milliliters of toluene in two batches, continuing distillation is that 110 ℃ of distillations stop up to gas phase temperature, cool to below 60 ℃, from dropping funnel, drip 0.124 mol phosphorus trichloride again, and 60～70 ℃ of reactions 1 hour.Dropping content is 95.5% N-(2 under this temperature, the 6-xylyl) alanine methyl esters 0.2 mol, heating reflux reaction 1 hour.Emitting hydrogen chloride gas in the reaction absorbs with water.Cooling adds 150 milliliters in cold water then, stirs standing demix, and organic phase precipitation, raffinate incline and, cool off the yellow solid product, content 93.5%, yield 96.2%.
Synthetic example two
0.2 mol Mono Chloro Acetic Acid is added there-necked flask, add 15 ml methanol.Start to stir and make the Mono Chloro Acetic Acid dissolving.Then, adding 0.4 mol content from dropping funnel is the methanol solution of 28.30% sodium methylate, and adding was also reacted 40 minutes under reflux temperature.Steam 70% methyl alcohol of methyl alcohol total amount in the there-necked flask then, add 150 milliliters of toluene, continue distillation, treat that toluene 80% is added 150 milliliters of toluene after being steamed again in the there-necked flask, be distilled to 110 ℃ of column temperatures, cool to 40 ℃.Drip 0.25 molar sulfur oxychloride from dropping funnel, heating drips N-(2, the 6-xylyl then 60～75 ℃ of reactions 1 hour under this temperature) alanine methyl esters 0.18 mol, reacting by heating 1 hour is emitted sulfurous gas and hydrogen chloride gas absorbs with alkali lye.Cool 30～40 ℃, 150 ml waters are added stirring, layering, the organic phase precipitation, residual solids is a product.Yield 97%, content 95.2%.
Claims (4)
1, the preparation method of metaxanin, it is characterized in that making behind the methoxyacetic acid sodium without the direct chloride of acidifying by Mono Chloro Acetic Acid or sodium chloroacetate and sodium methylate, intermediate product methoxyacetic acid sodium and methoxyacetyl chloride are without separating, make methoxylation, chloride and amidate action be the method for prepared in reaction metaxanin in same reactor successively, and all acyl chlorinating agents all can be used to prepare methoxyacetyl chloride, further Metalaxyl synthesizing, wherein Zui Jia acyl chlorinating agent has: phosphorus trichloride, phosphorus oxychloride, phosphorus pentachloride, sulfur oxychloride, phosgene etc., after finishing, reaction adds water stratification, make product behind the organic phase precipitation, producing the raw materials used mole ratio of metaxanin is: N-(2, the 6-3,5-dimethylphenyl) alanine methyl esters: Mono Chloro Acetic Acid: sodium methylate: acyl chlorinating agent=1.0: 1.05～1.4: 2.1～2.8: 0.5～1.8, the temperature of reaction of preparation methoxyacetic acid sodium is 30～70 ℃, reaction times is 0.5～2.0 hour, the temperature of reaction of preparation methoxyacetyl chloride is 30～110 ℃, reaction times is 05～30 hour, the temperature of reaction of preparation metaxanin is 30～110 ℃, and the reaction times is 0.5～4.0 hour.
2, method according to claim 1, the most suitable reaction temperature that it is characterized in that producing methoxyacetic acid sodium is 50～70 ℃, the peak optimization reaction time is 1.0～2.0 hours.
3, method according to claim 1, the most suitable reaction temperature that it is characterized in that producing the methoxy Acetyl Chloride 98Min. is 60～70 ℃, the peak optimization reaction time is 1～2 hour.
4, method according to claim 1, the most suitable reaction temperature that it is characterized in that producing metaxanin is 80～110 ℃, the peak optimization reaction time is 1.0～2.0 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 89107346 CN1051906A (en) | 1989-11-21 | 1989-11-21 | The preparation method of metaxanin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 89107346 CN1051906A (en) | 1989-11-21 | 1989-11-21 | The preparation method of metaxanin |
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| Publication Number | Publication Date |
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| CN1051906A true CN1051906A (en) | 1991-06-05 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN 89107346 Pending CN1051906A (en) | 1989-11-21 | 1989-11-21 | The preparation method of metaxanin |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101088986B (en) * | 2007-06-09 | 2010-06-23 | 大庆石油管理局 | Metalaxyl synthesizing process |
| CN109180514A (en) * | 2018-07-03 | 2019-01-11 | 浙江禾本科技有限公司 | A kind of synthetic method of optical activity metalaxyl |
-
1989
- 1989-11-21 CN CN 89107346 patent/CN1051906A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101088986B (en) * | 2007-06-09 | 2010-06-23 | 大庆石油管理局 | Metalaxyl synthesizing process |
| CN109180514A (en) * | 2018-07-03 | 2019-01-11 | 浙江禾本科技有限公司 | A kind of synthetic method of optical activity metalaxyl |
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