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Method for synthesizing 2-methoxy-5-aminosulfonylmethyl benzoate by one-step method

A technology of methyl sulfamoylbenzoate and methyl chlorobenzoate, which is applied in the field of organic compound synthesis, can solve the problems of high processing cost, large amount of three wastes, long process route, etc., and achieve high yield, good quality and process short process effect

Inactive Publication Date: 2016-04-13
苏州诚和医药化学有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

like figure 1 As shown, its synthesis currently uses salicylic acid at home and abroad to obtain the product through methylation, chlorosulfonation, amination, and esterification. amount (COD), high salt, high ammonia nitrogen, mixed wastewater, etc., the treatment is difficult and the treatment cost is extremely high, which seriously restricts the large-scale industrial production of this product

Method used

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  • Method for synthesizing 2-methoxy-5-aminosulfonylmethyl benzoate by one-step method
  • Method for synthesizing 2-methoxy-5-aminosulfonylmethyl benzoate by one-step method

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Experimental program
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Effect test

Embodiment 1

[0016] Such as figure 2 In the synthetic route shown, 300g of tetrahydrofuran, 50g (0.25mol) of methyl 2-methoxy-5-chlorobenzoate, and 1.25g of cuprous chloride (0.0125mol) will be added to a 1000ml reaction bottle equipped with a reflux device , 25.7g (0.25mol) sodium sulfinate, heated to 45 ° C, and kept at this temperature for 12 hours, after the heat preservation was completed, 2 grams of activated carbon was added to the reaction solution and filtered under heat, and the filtrate was concentrated to dryness under reduced pressure, 60 It was dried under vacuum at ℃ to obtain 57.9 g (0.236 mol) of white crystalline powder of methyl 2-methoxy-5-sulfamoylbenzoate, with a yield of 94.5% and a content of 99.51% (HPLC).

[0017] Among them, HPLC detection conditions: mobile phase: 700 milliliters of water; 200 milliliters of methanol. Detection wavelength: 240nm, flow rate 1.0ml / min, sample 0.01g, dilute to 25ml with mobile phase, injection volume 5μl.

Embodiment 2

[0019] Such as figure 2 In the synthetic route shown, 300g of tetrahydrofuran, 50g (0.25mol) of methyl 2-methoxy-5-chlorobenzoate, and 2.5g (0.025mol) of cuprous chloride will be added to a 1000ml reaction bottle equipped with a reflux device , 26.8g (0.26mol) sodium sulfinate, heated to 50 ° C, and kept at this temperature for 16 hours, after the heat preservation was completed, 2 grams of activated carbon was added to the reaction solution and filtered under heat, and the filtrate was concentrated to dryness under reduced pressure, 60 It was dried under vacuum at ℃ to obtain 58.3 g (0.238 mol) of white crystalline powder of methyl 2-methoxy-5-sulfamoylbenzoate, yield 95.09%, content 99.66% (HPLC).

[0020] Among them, HPLC detection conditions: mobile phase: 700 milliliters of water; 200 milliliters of methanol. Detection wavelength: 240nm, flow rate 1.0ml / min, sample 0.01g, dilute to 25ml with mobile phase, injection volume 5μl.

Embodiment 3

[0022] Such as figure 2 In the synthetic route shown, 300g of tetrahydrofuran, 50g (0.25mol) of methyl 2-methoxy-5-chlorobenzoate, 2g (0.02mol) of cuprous chloride will be added to a 1000ml reaction flask equipped with a reflux device, 28.3g (0.275mol) sodium sulfinate, heat up to 60°C, and keep at this temperature for 8 hours. After the heat preservation is over, add 2 grams of activated carbon to the reaction solution and filter it under heat. The filtrate is concentrated under reduced pressure to dryness, After vacuum drying, 59.2 g (0.241 mol) of white crystalline powder of methyl 2-methoxy-5-sulfamoylbenzoate was obtained, with a yield of 96.55% and a content of 99.51% (HPLC).

[0023] Among them, HPLC detection conditions: mobile phase: 700 milliliters of water; 200 milliliters of methanol. Detection wavelength: 240nm, flow rate 1.0ml / min, sample 0.01g, dilute to 25ml with mobile phase, injection volume 5μl.

[0024] As can be seen from Examples 1-3, the advantages of...

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Abstract

The invention provides a method for synthesizing 2-methoxy-5-aminosulfonylmethyl benzoate by a one-step method. The method is characterized by adding 2-methoxy-5-methyl chlorobenzoate, sodium amino sulfonate, a solvent and a catalyst to a reaction device and controlling the temperature at 45-60 DEG C to react for 8-16 hours; adding activated carbon for decoloration after reaction is completed and removing activated carbon, the catalyst and a byproduct sodium chloride through filtration; carrying out vacuum concentration on the filtrate, thus obtaining 2-methoxy-5-aminosulfonylmethyl benzoate, wherein the mole ratio of 2-methoxy-5-methyl chlorobenzoate to sodium amino sulfonate is 1 to (1-1.1). The method for synthesizing 2-methoxy-5-aminosulfonylmethyl benzoate by the one-step method has the advantages that the original technological process is short; the yield is high; the quality is good; no three wastes polluting the environment are generated, so that the method is very environment-friendly and is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, in particular to a method for synthesizing methyl 2-methoxy-5-sulfamoylbenzoate in one step. Background technique [0002] Methyl 2-methoxy-5-sulfamoylbenzoate is an important intermediate of antipsychotic drugs sulpiride and levosulpiride. Such as figure 1 As shown, its synthesis currently uses salicylic acid at home and abroad to obtain the product through methylation, chlorosulfonation, amination, and esterification. COD, high salt, high ammonia nitrogen, mixed wastewater, etc., the treatment is difficult and the treatment cost is extremely high, which seriously restricts the large-scale industrial production of this product. The present invention adopts a brand-new process and line, adopts sodium sulfinate and 2-methoxy-5-chlorobenzoic acid methyl ester in the presence of a small amount of catalyst, and directly condenses to obtain the product, which greatly shortens its ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/36C07C303/44C07C311/29
CPCC07C303/36C07C303/44C07C311/29
Inventor 夏秋景
Owner 苏州诚和医药化学有限公司
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