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Synthesis method of 2-methoxyl-5-amino sulfanoylmethyl benzoate

A technology of methyl sulfamoyl benzoate and methyl chlorobenzoate, applied in the field of organic compound synthesis, can solve the problems of long process route, large amount of three wastes and high treatment cost, and achieves short process flow, good quality and high yield high effect

Inactive Publication Date: 2016-05-25
苏州诚和医药化学有限公司
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  • Summary
  • 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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  • Synthesis method of 2-methoxyl-5-amino sulfanoylmethyl benzoate
  • Synthesis method of 2-methoxyl-5-amino sulfanoylmethyl benzoate

Examples

Experimental program
Comparison scheme
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 , 26.285g (0.255mol) sodium sulfinate, heated to 65 ° 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 by 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 45 ° 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 40°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 to dryness under reduced pressure, at 60°C 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 advan...

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Abstract

The invention provides a synthesis method of 2-methoxyl-5-amino sulfanoyl methyl benzoate. The synthesis method comprises the following steps: adding 2-methoxyl-5-chloromethyl benzoate, amino sodium sulfinate, a solvent and a catalyst into a reaction device; controlling the temprature to be 40 DEG C to 65 DEG C to react for 8 to 16 hours; after the reaction is finished, adding active carbon for de-coloring; filtering to remove the active carbon, the catalyst and a byproduct sodium chloride; concentrating under reduced pressure a filtrate to obtain the 2-methoxyl-5-sulfamoyl methyl benzoate. The synthesis method of the 2-methoxyl-5-sulfamoyl methyl benzoate, provided by the invention, has the advantages of short original technological process, high yield and good quality, has no three wastes which pollute the environment, is very environmental 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 2-methoxy-5-sulfamoylbenzoic acid methyl ester. 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 sy...

Claims

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Application Information

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IPC IPC(8): C07C303/36C07C311/29
CPCC07C303/36
Inventor 夏秋景
Owner 苏州诚和医药化学有限公司
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