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The preparation 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 preparing methyl 3-benzoate, can solve the problems of large amount of waste water, high production cost, inability to recycle catalysts, etc., and achieve small amount of waste water, The effect of lower production cost and less catalyst consumption

Inactive Publication Date: 2018-09-07
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0020] The process uses a large amount of catalyst, and the catalyst cannot be recycled, resulting in a large amount of waste water, resulting in high production costs

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1, a kind of preparation method of 3-(2-amino-2-thioethyl) methyl benzoate, carries out following steps successively:

[0047] 1), in the 500ml autoclave with stirring and temperature control, add 3-cyanomethylbenzoic acid methyl ester 88.3g (99.2wt%, 0.5mol), water 130ml, acetamidine hydrochloride 4.4g (accounting for raw material 5wt%), also add about 3.7g of 70% (mass %) NaSH, thereby adjust the pH value to about 10; Pass into H 2 S gas until the reaction pressure is 0.5MPa, stir and raise the temperature to about 70°C, and stop the reaction after 4 hours of heat preservation reaction (at this time, the system pressure remains unchanged);

[0048] 2), after stopping the reaction, cool to room temperature, the H in the kettle 2 S gas is absorbed with concentrated lye (NaOH solution with a mass concentration of 50%), 5 wt% dilute hydrochloric acid is added dropwise to the kettle liquid to adjust the solution to pH=6-7, filtered, the filtrate is recycled, and ...

Embodiment 2

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

[0050] 1), add 88.3g (99.2wt%, 0.5mol) of methyl 3-cyanomethylbenzoate, water 150ml, acetamidine hydrochloride 2.6g (accounting for raw material) in the 500ml autoclave with stirring and temperature control 3wt%), also add about 2.2g of 70%NaSH, thereby adjust the pH value to about 9; Pass into H 2 S gas until the reaction pressure is 0.5MPa, stir and raise the temperature to about 75°C, and stop the reaction after 4.5h of heat preservation reaction (at this time, the system pressure remains unchanged);

[0051] 2), after stopping the reaction, cool to room temperature, the H in the kettle 2 S gas is absorbed with concentrated alkali solution, 5wt% dilute hydrochloric acid is added dropwise to the kettle liquid to adjust the solution to pH=6-7, filtered, the filtrate is recycled, the filter cake is washed with water (1×200ml), filtered, and d...

Embodiment 3

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

[0053] 1), in the 500ml autoclave with stirring and temperature control, add 3-cyanomethylbenzoic acid methyl ester 88.3g (99.2wt%, 0.5mol), water 150ml, propionamidine hydrochloride 3.5g (accounting for raw material 4wt%) also add about 2.6g of 70%NaSH, thereby adjust the pH value to about 9; Pass into H 2 S gas until the reaction pressure is 0.7MPa, stir and raise the temperature to about 85°C, and stop the reaction after holding the heat for 3 hours (the system pressure remains unchanged at this time);

[0054] 2), after stopping the reaction, cool to room temperature, the H in the kettle 2 S gas is absorbed with concentrated alkali solution, 5wt% dilute hydrochloric acid is added dropwise to the kettle liquid to adjust the solution to pH=6-7, filtered, the filtrate is recycled, the filter cake is washed with water (1×200ml), filtered, a...

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Abstract

The invention discloses a preparation method of 3-(2-amino-2-sulfoethyl)methyl benzoate. The preparation method of 3-(2-amino-2-sulfoethyl)methyl benzoate comprises the following steps: 1) performing reaction in a high-pressure kettle at the reaction temperature of 50 to 100 DEG C for 2 to 6 hours by taking 3-cyanomethyl methyl benzoate as a raw material, water as a solvent and amidine hydrochloride as a catalyst, adjusting the pH value to be more than or equal to 9 and introducing H2S to control the pressure to be 0.3 to 3 Mpa, wherein the mass of the catalyst is 1 to 10 percent that of the raw material; 2) performing aftertreatment: after the reaction in the step 1) is finished, cooling the high-pressure kettle to room temperature, absorbing the H2S gas by using concentrated alkaline liquid, adjusting the pH value of the reaction liquid in the high-pressure kettle by using diluted hydrochloric acid to be 6 to 7, filtering, washing the filter cake with water, filtering and drying to obtain 3-(2-amino-2-sulfoethyl)methyl benzoate.

Description

technical field [0001] The invention relates to a method for preparing methyl 3-(2-amino-2-thioethyl)benzoate from methyl 3-cyanomethylbenzoate through thiolation. Background technique [0002] 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. [0003] [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 reacts 3h, obtains product 3-(2-amino-2-thioethyl) met...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C327/44
CPCC07C327/44
Inventor 陈新志高武成钱超
Owner ZHEJIANG UNIV
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