Method for synthesizing 4-(2-aminoethyl)benzsulfamide

A technology of benzenesulfonamide and aminoethyl, which is applied in the field of type Ⅱ diabetes hypoglycemic drug intermediates and the synthesis of 4-(2-aminoethyl)benzenesulfonamide, which can solve the problem of increasing equipment investment costs and shortening equipment life cycle , low utilization rate of chlorosulfonic acid, etc., to achieve the effect of low cost, reusable by-products, and easy promotion and application

Inactive Publication Date: 2017-01-18
姜近仁
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Benefits of technology

This patented process involves making certain compounds from beta - phenylethynyarnitrile (BEN). By reacting this starting substance with another molecule called BPEI or an alkoxysulfinate ester derivative like bis(dim ethanolimony)-N-(methanesuccyanato)) at specific temperatures, these new products are made that have improved properties compared to existing methods. These improvements include lower manufacturing costs due to less useable ingredients, easier handling during processing, more efficient utilization of resources, longer lifespans on equipment, and ease of implementation across various industries.

Problems solved by technology

This patented technical problem addressed in this patents relates to improving the efficiency and effectiveness of chemicals called 4-(aminothiazolium)-iminobutylenediamine (FTY), an antihyperglycaemia drug commonly prescribed worldwide because they have several important uses including treatments against metabolism abnormalities associated diseases like cardiac conditions caused by hypertension and renal damage from chronic kidney failures. These medications include both new agents and improved methods involving chemistry techniques.

Method used

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Examples

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Effect test

Embodiment 1

[0026] A method for synthesizing 4-(2-aminoethyl)benzenesulfonamide, the concrete steps are as follows:

[0027] Step 1) Acetylation reaction

[0028] Using β-phenylethylamine and acetic acid as raw materials, put 300kg of acetic acid into a clean 1000L reactor (with full reflux device), stir and add 300kg of β-phenylethylamine into it, heat up, reflux, and count for 4 hours. After the reaction is completed, it is recovered by distillation Dilute acetic acid, normal pressure in the early stage, decompression in the later stage, distill the dilute acetic acid as much as possible, cool, and collect 390.5kg of acetylated product (ie N-acetylphenylethylamine). Add 180 kg of solvent into the reaction feed liquid, stir and mix evenly to form a mixed liquid for later use. The solvent is chloroform, and the weight yield of acetylate (ie N-acetylphenethylamine) is 130%. The solvent can be selected from dichloromethane, chloroform, carbon tetrachloride or dichloroethane, preferably ch...

Embodiment 2

[0041] Step 1) Acetylation reaction:

[0042] Replace acetic acid with acetic anhydride, ratio β-phenylethylamine: acetic anhydride=1:1 (weight ratio), other conditions are the same as in Example 1. The reaction yield was 95% (weight yield).

[0043] Step 2) Chlorosulfonation reaction:

[0044] Acetyl compound (being N-acetyl phenethylamine) 390.5kg, the consumption of chlorosulfonic acid is 936kg, and the consumption of chlorinating agent (selecting phosphorus pentachloride) is 390.5kg, and other conditions are with embodiment 1, and reaction is finished, and weight yield is 130%.

[0045] Step 3) Amination reaction:

[0046] Mass percentage concentration is that 25% ammoniacal liquor consumption is 1660kg, and other conditions are with embodiment 1, and reaction finishes, and weight yield is 55%.

[0047] Step 4) Hydrolysis reaction:

[0048] Sodium hydroxide lye mass percentage concentration is 25%, and other conditions are with embodiment 1, and reaction finishes, and...

Embodiment 3

[0052] Step 1) Acetylation reaction:

[0053] Select β-phenylethylamine and acetic acid reaction, but solubilizer is carbon tetrachloride, other conditions are with embodiment 1, and weight yield is 128%.

[0054] Step 2) Chlorosulfonation reaction:

[0055] Reaction condition is the same as embodiment 1, and solvent selects carbon tetrachloride, and weight yield is 150%.

[0056] Step 3) Amination reaction:

[0057] Reaction condition is the same as embodiment 1, and solvent selects carbon tetrachloride, and weight yield is 55%.

[0058] Step 4) Hydrolysis reaction:

[0059] The reaction conditions are the same as in Example 1, and the reaction weight yield is 80%.

[0060] Step 5) Refining process:

[0061] Refining conditions are the same as in Example 1, and the reaction weight yield is 85%.

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Abstract

The invention aims at solving the technical problem of providing a method for synthesizing 4-(2-aminoethyl)benzsulfamide, and beta-phenylethylamine is used as a raw material, and is subjected to an acetylation reaction, a chlorosulfaonationreaction, an amination reaction, a hydrolysis reaction and purification to obtain the finished product 4-(2-aminoethyl)benzsulfamide. The method has the effects of being easily available in raw materials, low in cost, small in amount of chlorosulfonic acid in the chlorosulfaonation reaction, less in wastewater quantity, high in production yield, recyclable in by-products and beneficial to popularization and application. The product prepared by the method can be used in the synthesis and production of sulfonylurea hypoglycemic drugs, such as glipizide, glimepiride, gliquidone and glibenclamide. According to the method, cheap chemical materials are adopted, the reaction is simple and easy to operate, the problems of expensive raw materials and difficult operation of the reaction conditions at home and abroad are overcome, the production cost is reduced and the industrialization is achieved easily.

Description

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Claims

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Application Information

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Owner 姜近仁
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