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Preparation method of taurylamine hydrochloride

A technology of taurine hydrochloride and taurine, which is applied in the field of preparation of taurine hydrochloride, can solve problems such as low safety, large environmental pollution, and difficult post-processing, so as to simplify the process and reduce production costs , handle simple effects

Active Publication Date: 2016-10-12
CHANGZHOU SUNLIGHT PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This route uses taurine (compound of formula 2) as the starting material, and it is prepared through five steps of amino protection, chlorination, ammonolysis, deprotection, and salt formation. The disadvantages of this route are: (1) using The amino protection reaction temperature of phthalic anhydride is relatively high, which needs to be above 110°C, and it needs to be deprotected by highly toxic hydrazine hydrate, which is less safe; (2) the chlorination reaction using phosphorus pentachloride not only Difficulty in reprocessing and greater environmental pollution

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0026] The preparation method of the taurine hydrochloride of the present embodiment has the following steps:

[0027] ①Add 80g of taurine (0.64mol), 160g of water, 93.4g of 27.4wt% sodium hydroxide solution and 80mL of tetrahydrofuran into the reaction flask, stir and cool down to 5±2°C. Add 115g of benzyl chloroformate (0.67mol) dropwise and finish dropping in about 1 hour, then continue to add 93.4g of sodium hydroxide solution with a concentration of 27.4wt% dropwise, keep warm at 10±2°C and react after 2 hours Completely, benzyloxycarbonylaminoethanesulfonic acid is obtained.

[0028] Concentrate tetrahydrofuran under reduced pressure, extract with ethyl acetate (200mL×2), add 500mL of toluene to the water phase, raise the temperature to reflux and separate the water until no water drops are separated, and it is directly used in the next reaction.

[0029] The reaction formula is as follows:

[0030] .

[0031] ②Under the protection of nitrogen, add 5mL of DMF to the...

Embodiment 2～ Embodiment 5）

[0044] The method of each embodiment is basically the same as that of Example 1, the difference lies in step ④, see Table 1 for details.

[0045] Table 1

[0046] Example 1 Example 2 Example 3 Example 4 Example 5 water 160mL 65mL - 605mL 380mL Concentrated hydrochloric acid 160mL 240mL 300mL 80mL 120mL product weight 61.2g 61.5g 62.0g 60.6g 61.0g purity 99.3% 99.4% 99.5% 99.0% 99.1% yield 91.0% 91.5% 92.2% 90.1% 90.7%

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Abstract

The invention discloses a preparation method of taurylamine hydrochloride. The preparation method comprises the following steps: by using taurine as an initial raw material, sequentially carrying out amino protecting reaction, chlorination reaction, ammonolysis reaction and deprotection-salification to obtain the taurylamine hydrochloride. The amino protecting group adopted by the amino protecting reaction is benzyl chloroformate, and the amino protecting group is carried out at 5-15 DEG C in the presence of sodium hydroxide and water. The chlorination reagent adopted by the chlorination reaction is thionyl chloride, and the chlorination reaction temperature is 60-70 DEG C. The ammonolysis reaction is carried out in tetrahydrofuran under the action of stronger ammonia water, and the ammonolysis reaction temperature is 5-15 DEG C. The total yield of the four-step reaction can reach 80% or above, the product purity can reach 99% or above, and thus, the method is suitable for industrialized mass production.

Description

technical field [0001] The invention belongs to the technical field of medicine and chemical industry, and in particular relates to a preparation method of taurine hydrochloride. Background technique [0002] The chemical name of taurine hydrochloride is 2-aminoethylsulfonamide hydrochloride, which is a widely used non-antibiotic anti-infective drug, and its structural formula is as shown in formula 1: [0003] . [0004] The existing route of preparing taurine hydrochloride is as follows: [0005] . [0006] This route uses taurine (compound of formula 2) as the starting material, and it is prepared through five steps of amino protection, chlorination, ammonolysis, deprotection, and salt formation. The disadvantages of this route are: (1) using The amino protection reaction temperature of phthalic anhydride is relatively high, which needs to be above 110°C, and it needs to be deprotected by highly toxic hydrazine hydrate, which is less safe; (2) the chlorination reac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/38C07C311/32C07C303/02C07C309/83C07C303/22C07C309/15
CPCC07C303/02C07C303/22C07C303/38C07C311/32C07C309/83C07C309/15Y02P20/55
Inventor 胡国宜胡锦平吴建华薛建伟汪士金钱王科鲁炜闵彐峰
Owner CHANGZHOU SUNLIGHT PHARMA
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