Preparation method of high-purity 5-vinyl oxazolidine-2-thioketone

A high-purity technology of oxazolidine, which is applied in the field of organic chemical industry, can solve the problem of low purity of 5-vinyloxazolidine-2-thione, and achieve the effect of low cost, convenient operation and simple steps

Inactive Publication Date: 2015-03-25
SHANGHAI INST OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Aiming at the above-mentioned technical problems in the prior art, the invention provides a kind of preparation method of high-purity 5-vinyl oxazolidine-2-thione, described this high-purity 5-vinyl oxazolidine-2 -The preparation method of thione should solve the technical problem that the preparation method in the prior art obtains the low purity of 5-vinyl oxazolidine-2-thione

Method used

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  • Preparation method of high-purity 5-vinyl oxazolidine-2-thioketone

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Effect test

Embodiment 1

[0037] A kind of preparation method of high-purity 5-vinyl oxazolidine-2-thione:

[0038] Dissolve 1-amino-3-buten-2-ol (480 mg) in water (20 mL), add potassium hydroxide (0.38 g) and carbon disulfide (0.44 mL), stir well, and heat the oil bath to 60 ℃, and then a mixed aqueous solution (15 mL) containing potassium hydroxide (0.44 g) and lead nitrate (2.21 g) was added to the reaction system, and the temperature of the oil bath was kept constant, and stopped after heating for 75 min. The black precipitate was removed by centrifugation, the supernatant was taken and rotated in a water bath at 50 °C, and the remaining solid was dissolved with saturated sodium chloride solution (15 mL), extracted with 3 times the volume of ethyl acetate, and evaporated to dryness to obtain 5- The crude product of vinyloxazolidine-2-thione (498 mg) was 70% in yield and 80% in purity.

[0039] Then the crude product was dissolved in distilled water (166 mL) to prepare an aqueous solution (30 mg / mL...

Embodiment 2

[0046] A kind of preparation method of high-purity 5-vinyl oxazolidine-2-thione:

[0047] Dissolve 1-amino-3-buten-2-ol (830 mg) in water (35 mL), add potassium hydroxide (0.66 g) and carbon disulfide (0.76 mL), stir well, and heat the oil bath to 60 ℃, and then a mixed aqueous solution (26 mL) containing potassium hydroxide (0.76 g) and lead nitrate (3.82 g) was added to the reaction system, and the temperature of the oil bath was kept constant, and stopped after heating for 75 min. The black precipitate was removed by centrifugation, the supernatant was taken and rotated in a water bath at 50 °C, and the remaining solid was dissolved with saturated sodium chloride solution (26 mL), extracted with 3 times the volume of ethyl acetate, and evaporated to dryness to obtain 5- The crude product of vinyloxazolidine-2-thione (837 mg) has a yield of 68% and a purity of 80%.

[0048] Then the crude product was dissolved in distilled water (24 mL) to prepare an aqueous solution (35 mg...

Embodiment 3

[0051] A kind of preparation method of high-purity 5-vinyl oxazolidine-2-thione:

[0052] Dissolve 1-amino-3-buten-2-ol (1700 mg) in water (71 mL), add potassium hydroxide (1.35 g) and carbon disulfide (1.56 mL), stir well, and heat the oil bath to 60 ℃, and then a mixed aqueous solution (53 mL) containing potassium hydroxide (1.56 g) and lead nitrate (7.83 g) was added to the reaction system, and the temperature of the oil bath was kept constant, and stopped after heating for 75 min. The black precipitate was removed by centrifugation, the supernatant was taken and rotated in a water bath at 50 °C, and the remaining solid was dissolved with saturated sodium chloride solution (53 mL), extracted with 3 times the volume of ethyl acetate, and evaporated to dryness to obtain 5- The crude product of vinyloxazolidine-2-thione (1638 mg) has a yield of 65% and a purity of 80%.

[0053] Then the crude product was dissolved in distilled water (41 mL) to prepare an aqueous solution of t...

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Abstract

The invention discloses a preparation method of high-purity 5-vinyl oxazolidine-2-thioketone. The preparation method comprises the following steps: carrying out coordination on 1-amino-3-butene-2-alcohol taken as a starting material by using lead nitrate water solution, carrying out annulation on the raw material and CS2 in alkaline environment of potassium hydroxide solution, filtering the reaction liquid, extracting the reaction liquid by using ethyl acetate, carrying out liquid separation, drying and rotary evaporation to obtain a crude product, purifying the water solution containing the crude product through a preparative liquid chromatograph, receiving a mobile phase in the retention time period of a target product, and carrying out rotary evaporation and drying to obtain the product. According to the method, the steps are simple, the operation is convenient, the cost is low and the output is relatively high; and according to the method, the single-pass preparation amount can be up to 0.2-0.3g and the purity is 99.0-99.5%.

Description

technical field [0001] The invention belongs to the field of organic chemical industry, in particular to a method for preparing 5-vinyloxazolidine-2-thione, specifically a method for preparing high-purity 5-vinyloxazolidine-2-thione . Background technique [0002] 5-vinyloxazolidine-2-thione (as figure 1 Shown) also known as DL-Gaoyichun, anti-goiter hormone, it is an anti-viral active ingredient present in Brassica and Brassicaceae plants, and has been widely used in the field of medicine. At present, the preparation of this product is mainly based on extraction from natural products, the preparation cost is relatively high, and it is rarely prepared by synthetic methods. The existing reported synthetic methods have the following routes: [0003] 1. (B. Bernardi, M. G. Finiguerra, A. A. Rossi, S. Palmieri. J. Agric. Food Chem. 2003, 51, 2737.) The reaction scheme of its preparation process is as follows figure 2 As shown, the epi-progoitrin was hydrolyzed with myrosina...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/16
CPCC07D263/16
Inventor 许旭黄晨殷燕
Owner SHANGHAI INST OF TECH
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