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Synthesis method of oxadiazon intermediate

A synthesis method and intermediate technology, applied in the field of synthesis of oxadiazone intermediates, can solve the problems of polluting the environment, difficulty in recycling waste acid and waste water, etc., and achieve the effects of avoiding pollution, great application value, and increased yield

Inactive Publication Date: 2019-06-21
ANHUI RES INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Among them, the intermediate product 2,4-dichloro-5-isopropoxyaniline in the synthesis route is obtained through esterification, nitration, hydrolysis, etherification, and reduction. This synthesis method will produce a large amount of waste acid that is difficult to recycle. and waste water, seriously polluting the environment

Method used

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  • Synthesis method of oxadiazon intermediate
  • Synthesis method of oxadiazon intermediate
  • Synthesis method of oxadiazon intermediate

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preparation example Construction

[0045] The invention discloses a synthesis method of an oxadiazone intermediate, specifically discloses a synthesis method of an oxadiazone intermediate amine ether, comprising the following steps:

[0046] S1, take m-aminophenol as the initial raw material;

[0047] S2, performing an acylation reaction on m-aminophenol to obtain a reaction solution A;

[0048] S3, performing a chlorination reaction on the reaction solution A to obtain 2,4-dichloro-5-hydroxyacetanilide;

[0049] S4. Etherifying 2,4-dichloro-5-hydroxyacetanilide to obtain 2,4-dichloro-5-isopropoxyacetanilide;

[0050] S5. Deprotecting 2,4-dichloro-5-isopropoxyacetanilide to obtain 2,4-dichloro-5-isopropoxyacetaniline.

[0051] Wherein, the step of acylation reaction is:

[0052] Add m-aminophenol into the acylation solvent and stir to dissolve;

[0053] Add acetic anhydride dropwise to the stirred solution, and carry out acylation reaction under heating conditions to obtain m-hydroxyaniline solution, which ...

Embodiment 1

[0088] (1) Acylation reaction:

[0089] In the 500ml four-neck round-bottomed flask equipped with mechanical stirring, thermometer and condenser tube, add m-aminophenol 55 grams, water 280 grams, acetic anhydride 62 grams, then stir 5 minutes;

[0090] Heating up to 110°C, and under the condition of 110°C, reflux reaction for 3 hours;

[0091] After the reflux reaction finishes, cool to 0 degree and filter to obtain a filter cake;

[0092] Wash the filter cake with a small amount of ice water, and dry the filter cake in a vacuum dryer to obtain 72 grams of off-white 3-hydroxyacetanilide solid, with a yield of 95.4%;

[0093] The 3-hydroxyacetanilide solid was added to a 1000 ml three-neck flask equipped with a thermometer and mechanically stirred, and 400 g of acetonitrile solvent was added and stirred to dissolve.

[0094] (2) Chlorination reaction:

[0095] Under normal temperature conditions, slowly add 145 grams of sulfuryl chloride solution dropwise to the three-necked...

Embodiment 2

[0111] (1) Acylation reaction:

[0112] In a 1000ml four-necked round-bottomed flask equipped with a mechanical stirrer, a thermometer and a condenser, add 55 grams of m-aminophenol and 450 grams of acetonitrile and stir to dissolve at normal temperature;

[0113] Then slowly add 76.5 grams of acetic anhydride to react at normal temperature for 3 hours;

[0114] The end point of the reaction is monitored until the end point of the reaction is reached, and the acetonitrile system is obtained, and the chlorination reaction is carried out.

[0115] (2) Chlorination reaction:

[0116] Under normal temperature conditions, in the acetonitrile system obtained by the acylation reaction, slowly add 150 grams of sulfuryl chloride solution dropwise, after the dropwise addition is completed, react for 3 hours;

[0117] Liquid phase tracking monitors the reaction end point until the reaction end point is reached;

[0118] Then it was cooled to 0° C., the solid was precipitated, and then...

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Abstract

The invention discloses a synthesis method of an oxadiazon intermediate. The synthesis method comprises following steps: m-aminophenol is taken as an initial raw material; m-aminophenol is subjected to an acylation reaction, and a reaction solution A is obtained; the reaction solution A is subjected to a chlorination reaction, and 2,4-dichloro-5hydroxyacetanilide is obtained; 2,4-dichloro-5hydroxyacetanilide is subjected to an etherification reaction, and 2,4-dichloro-5isopropoxyacetaniline is obtained; 2,4-dichloro-5isopropoxyacetaniline is subjected to deprotection, and 2,4-dichloro-5isopropoxyaniline is obtained. With the adoption of the synthesis method of 2,4-dichloro-5-isopropoxyaniline, environmental pollution is avoided, few technological steps are required, and the yield is high.

Description

technical field [0001] The invention relates to a herbicide production technology, in particular to a synthesis method of an oxadiazone intermediate. Background technique [0002] Oxadiazon is a protoporphyrinogen oxidase inhibitor selective pre-emergent and post-emergent herbicide variety, mainly used for controlling a variety of annual monocotyledonous and dicotyledonous weeds, mainly used for weeding in paddy fields, and for peanuts in dry fields. , cotton, sugarcane, etc. are also effective; contact herbicides before and after emergence. It has the characteristics of high efficiency, long-term effect, broad spectrum, low dosage, safety to humans, animals and the environment, mild to insect natural enemies and beneficial organisms, etc., and has a broad market prospect. [0003] At present, the industrial synthetic route of oxadiazone mainly uses 2,4-dichlorophenol as raw material, and undergoes esterification, nitration, hydrolysis, etherification, reduction, diazotizat...

Claims

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Application Information

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IPC IPC(8): C07C217/84C07C213/02C07C233/25C07C231/02C07C231/12
Inventor 张家星潘正凯罗鸿文
Owner ANHUI RES INST OF CHEM IND
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