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Synthesis method of 3-(2-amino-2-thioethyl)methyl benzoate

A technology of methyl cyanomethyl benzoate and methyl benzoate, which is applied in the field of synthesizing methyl 3-benzoate, can solve problems such as strong organic weak acid odor, influence on catalytic effect, and easy volatilization of secondary amines, and achieve high product quality , fast reaction rate, simple post-processing effect

Inactive Publication Date: 2017-05-10
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0018] The organic weak acid used in this process has a strong odor, and the secondary amine has a low boiling point and is easily volatile, which affects the catalytic effect and causes a large amount of waste water

Method used

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  • Synthesis method of 3-(2-amino-2-thioethyl)methyl benzoate
  • Synthesis method of 3-(2-amino-2-thioethyl)methyl benzoate
  • Synthesis method of 3-(2-amino-2-thioethyl)methyl benzoate

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Experimental program
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Effect test

Embodiment 1

[0049] Embodiment 1, a kind of synthetic method of 3-(2-amino-2-thioethyl) methyl benzoate, carries out following steps successively:

[0050] 1), add 3-cyanomethylbenzoic acid methyl ester 35.3g (99.2wt%, 0.2mol), 70wt% (mass %) NaSH (24.0 g, 0.3mol) and methanol 80ml, the water bath is heated to about 70 ± 5 ° C, under the condition of mechanical stirring, the methanol solution (200ml) of triethylamine hydrochloride (41.3g, 0.3mol) is slowly added dropwise, and the addition time is 6h, continue to stir for 1h after the addition, and stop the reaction (the reaction process is tracked and detected by HPLC, when the remaining raw materials are less than 1%, stop the reaction).

[0051]2), after the reaction finishes, filter; Filter residue is NaCl, thereby realizes removing the NaCl that reaction generates; The filtrate is distilled (distillation temperature is respectively 68 ℃ and 90 ℃) thereby reclaims methanol (250ml) and triethylamine (38ml, about 0.27mol), the residue af...

Embodiment 2

[0052] Embodiment 2, a kind of synthetic method of 3-(2-amino-2-thioethyl) methyl benzoate, carry out following steps successively:

[0053] 1), add 3-cyanomethylbenzoic acid methyl ester 35.3g (99.2wt%, 0.2mol), 70wt% NaSH (24.0g, 0.28mol) in the 500ml four-neck flask that thermometer, reflux condenser and stirrer are equipped ) and methanol 80ml, the water bath temperature was raised to about 70±5°C, under the condition of mechanical stirring, slowly dropwise the methanol solution (200ml) of di-n-propylamine hydrochloride (38.5g, 0.28mol), the feeding time was 6h, and the feeding was finished After that, the stirring was continued for 1 h, and the reaction was stopped (the reaction process was tracked and detected by HPLC, and when the remaining raw material was less than 1%, the reaction was stopped).

[0054] 2), after the reaction is finished, filter; remove the NaCl generated by the reaction, distill the filtrate so as to reclaim methanol and di-n-propylamine, the still ...

Embodiment 3

[0055] Embodiment 3, a kind of synthetic method of 3-(2-amino-2-thioethyl) methyl benzoate, carries out following steps successively:

[0056] 1), add 3-cyanomethylbenzoic acid methyl ester 35.3g (99.2wt%, 0.2mol), 70wt% NaSH (24.0g, 0.3mol) in the 500ml four-necked flask that thermometer, reflux condenser and stirrer are equipped with ) and methanol 80ml, the temperature of the water bath was raised to about 70±5°C, under the condition of mechanical stirring, the methanol solution (200ml) of diisopropylamine hydrochloride (41.3g, 0.3mol) was slowly added dropwise, the feeding time was 6h, and the feeding was completed After that, the stirring was continued for 1 h, and the reaction was stopped (the reaction process was tracked and detected by HPLC, and when the remaining raw material was less than 1%, the reaction was stopped).

[0057] 2), after the reaction is finished, filter; remove the NaCl generated by the reaction, distill the filtrate to recover methanol and diisoprop...

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Abstract

The invention discloses a synthesis method of 3-(2-amino-2-thioethyl)methyl benzoate. The synthesis method comprises the following steps of 1), synthesis: first adding 3-cyanomethyl methyl benzoate, sodium hydrosulfide and methanol serving as a solvent into a vessel, raising temperature to 60 to 75 DEG C, dropwise adding a methanol solution of an organic amine hydrochloride into the vessel in an agitation condition, and after the methanol solution is completely dropwise added, continuously carrying out heat preservation and reaction for 1h to 2h in the agitation condition; 2), post treatment: filtering a reaction product obtained in the step 1) to remove NaCl generated in the reaction, distilling filter liquor obtained through filtration to recover the methanol and organic amine, and carrying out water scrubbing, the filtration and drying on a residue, which is formed after the filter liquor is distilled, in sequence, so that the 3-(2-amino-2-thioethyl)methyl benzoate is obtained.

Description

technical field [0001] The invention relates to a method for synthesizing 3-(2-amino-2-thioethyl) methyl benzoate from 3-cyanomethyl benzoate through thiolation. Background technique [0002] [0003] 3-(2-Amino-2-thioethyl)methyl benzoate is an important fine chemical raw material and pharmaceutical intermediate, and is a new type of phosphate transport inhibitor 2-[[3-[[4-(2 -Hydroxyethyl)-2-thiazolyl]methyl]benzoyl]amino]-5-(1-piperidinyl)-,(2E)-2-[[4-chloro-3-(trifluoromethane base) phenyl] methylene] benzohydrazine key intermediate, its structural formula is shown in S-1. [0004] There are 3-(2-amino-2-thioethyl) methyl benzoate synthetic methods reported in the literature as follows: [0005] Lewis, Jason G. et al. (WO2012006475) take 3-cyanomethylbenzoic acid methyl ester as raw material, triethylamine is catalyst (mass volume ratio of raw material and catalyst is 1:3), pyridine is solution, logical H 2 S reaction 3h obtains product 3-(2-amino-2-thioethyl) meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C327/44
CPCC07C327/44
Inventor 钱超高武成陈新志
Owner ZHEJIANG UNIV
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