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Method for synthesizing 5-chlorine-4-formyl oxazole

A technology of formyl oxazole and trichloromethyl is applied in the synthesis field of preparing 5-chloro-4-formyl oxazole, and can solve the problem that the utilization rate of chlorine atom of phosphorus oxychloride is not high, and the product is not easy to be separated and operated. Unsafe and other problems, to avoid phosphorus pollution, easy separation, good reaction selectivity

Active Publication Date: 2012-11-21
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

A large amount of phosphorus oxychloride in the traditional Vilsmeier reagent is used in the above reaction, and a large amount of phosphorus-containing wastes will be produced in industrial production, which makes the cost of processing the three wastes higher, and has unsafe operation, troublesome post-processing, and difficult separation of products. Disadvantages such as low utilization rate of chlorine atoms of phosphorus oxychloride

Method used

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  • Method for synthesizing 5-chlorine-4-formyl oxazole
  • Method for synthesizing 5-chlorine-4-formyl oxazole
  • Method for synthesizing 5-chlorine-4-formyl oxazole

Examples

Experimental program
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Effect test

Embodiment 1

[0027] In a 250ml four-neck flask equipped with a thermometer, reflux condenser and mechanical stirring, add benzoylglycine 18.9g (0.1mol), toluene 50ml, stir to dissolve at room temperature, add N,N-dimethylformamide (DMF ) 21.9g (0.3mol), bis(trichloromethyl)carbonate 29.7g (0.1mol), stirred at room temperature for 30 minutes, then heated to 100°C for 4 hours. After the reaction is complete, add 30ml of water, stir and hydrolyze at 50°C for 30 minutes, and cool to room temperature. After standing still, separate the water layer, keep the toluene layer, extract the water layer with 20ml toluene twice, combine all the toluene layers and wash with anhydrous sulfuric acid The sodium was dried, the solvent was distilled off, 90ml of n-hexane was added, and 16.56g of white solid was obtained after recrystallization, with a melting point of 92-93°C and a yield of 80%. IR (KBr): 3422, 3073, 1688, 1417cm -1 . 1 H NMR (400MHz, CDCl 3 )δ: 9.99 (s, 1H), 8.06 (d, 2H, J=6.8Hz), 7.48-7....

Embodiment 2

[0029] In a 250ml four-necked flask equipped with a thermometer, a reflux condenser and mechanical stirring, add benzoylglycine 18.9g (0.1mol), xylene 50ml, stir and dissolve at room temperature, add N,N-dimethylformamide ( DMF) 21.9g (0.3mol), bis(trichloromethyl)carbonate 29.7g (0.1mol), stirred at room temperature for 30 minutes, then heated to 100°C for 4 hours. After the reaction is complete, add 30ml of water, stir and hydrolyze at 50°C for 30 minutes, and cool to room temperature. After standing still, the water layer is separated, and the xylene layer is kept. The water layer is extracted 3 times with 20ml of xylene, and all the xylene layers are combined and used Dry over anhydrous sodium sulfate, distill off the solvent, add 90ml of n-hexane, and obtain 15.93g of white solid after recrystallization, with a melting point of 93-94°C and a yield of 77%.

Embodiment 3

[0031] In a 250ml four-neck flask equipped with a thermometer, reflux condenser and mechanical stirring, add benzoylglycine 18.9g (0.1mol), toluene 50ml, stir to dissolve at room temperature, add N,N-dimethylformamide (DMF ) 21.9g (0.3mol), bis(trichloromethyl)carbonate 59.4g (0.2mol), stirred at room temperature for 30 minutes, then heated to 100°C for 4 hours. After the reaction is complete, add 30ml of water, stir and hydrolyze at 100°C for 30 minutes, and cool to room temperature. After standing still, separate the water layer, keep the toluene layer, extract the water layer with 20ml of toluene three times, combine all the toluene layers and wash with anhydrous sulfuric acid The sodium was dried, the solvent was distilled off, 90ml of n-hexane was added, and 16.77g of white solid was obtained after recrystallization, with a melting point of 92-93°C and a yield of 81%.

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Abstract

The invention discloses a method for synthesizing 5-chlorine-4-formyl oxazole. The synthetic method comprise the steps of undergoing a reaction of a glycine derivative, bis(trichloromethyl) carbonic ester and a formamide compound in an organic solvent at a temperature of -20 DEG C to 150 DEG C for 1-10 hours and separating the reaction liquid after the reaction ends to obtain the 5-chlorine-4-formyl oxazole shown as a formula (I), wherein the ratio of the amount of substances of the glycine derivative to the formamide compound to the bis(trichloromethyl) carbonic ester is 1: (1-20): (0.33-3.3). In the invention, an acyl glycine derivative is firstly used as a raw material to synthesize a novel compound without using phosphorus oxychloride, thereby avoiding the phosphorus pollution and reducing the treatment cost of the three wastes; moreover, the reaction selectivity is good; the yield is high; the post treatment is simple and the product is easy to separate.

Description

(1) Technical field [0001] The present invention relates to a kind of synthetic method of 5-chloro-4-formyl oxazole, especially a kind of preparation 5-chloro-4-formyl oxazole with bis(trichloromethyl)carbonate (BTC) and formamide compound Synthetic method of acyl oxazole. (2) Background technology [0002] 5-chloro-4-formyl oxazole is an important pharmaceutical and chemical intermediate, and a series of derivatives (J.Chem.Soc. Perkin Trans. 1, 1993, 2259-2261). [0003] [0004] Before the present invention, there were few relevant reports on the synthetic method of 5-chloro-4-formyl oxazole. According to J.Chem.Soc.Perkin Trans.1, 1993, 2259-2261 report, it is proposed to use acyl glycine methyl ester derivatives as raw materials, through the Vilsmeier reaction of phosphorus oxychloride and N,N-dimethylformamide A small number of target products were synthesized with a total yield of about 56%. Apart from this, there are no other similar reports in the literature....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/34
Inventor 金灿苏为科陈俊
Owner ZHEJIANG UNIV OF TECH
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