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Method for synthesizing oxazole pyridone compound

A technology of oxazopyridone and synthesis method, applied in directions such as organic chemistry, can solve the problems of long production cycle and high cost, and achieve the effects of low production cost, short reaction time and high yield

Inactive Publication Date: 2009-08-05
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] (3) adopting carbonyldiimidazole and o-aminohydroxypyridine to synthesize oxazolpyridone, the cost of this synthetic method is too high;
[0006] (4) Adopt the two-step synthesis method of first synthesizing oxazolpyridinethione, then oxidatively synthesizing oxazolpyridinethione. This method has a long production cycle and a large amount of solid waste is produced

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Dissolve 0.4 mol of bis-trichloromethyl carbonate in 300 g of dichloroethane. Add 1mol 2-amino-3-hydroxypyridine and 3.5mol pyridine to the reaction flask, and slowly add the above dichloroethane solution of bistrichloromethylcarbonate dropwise at a temperature of 40°C. During the process, a light yellow solid substance was gradually precipitated. After the dropwise addition was completed, the heat preservation reaction was carried out for 1 hour, the solvent was recovered, and an appropriate amount of water was added to the residue, and the solid substance was precipitated. After filtration, the filter cake was washed twice with water, and dried to obtain Oxazopyridone 128.9g, yield 94.8%, melting point 211-212°C.

Embodiment 2

[0018] Dissolve 0.4 mol of bis-trichloromethyl carbonate in 350 g of chloroform. Add 1mol 2-amino-3-hydroxyl-5-chloropyridine and 3.5mol pyridine to the reaction flask, slowly add the above-mentioned trichloromethyl carbonate solution in chloroform at a temperature of 40°C, dropwise After completion, heat preservation reaction for 2 hours, recover the solvent, add an appropriate amount of water to the residue, and a solid substance is precipitated, filtered, the filter cake is washed twice with water, and dried to obtain 153.3 g of 6-chlorooxazopyridone, with a yield of 90.2 %, melting point 187-188°C.

Embodiment 3

[0020] Dissolve 0.4 mol of bis-trichloromethyl carbonate in 300 g of dichloroethane. Add 1mol 2-amino-3-hydroxypyridine, 6g pyridine, and 3mol triethylamine to the reaction flask, and slowly add the dichloroethane solution of the above-mentioned bistrichloromethyl carbonate at a temperature of 60°C, dropwise After the addition, keep the reaction for 1 hour, recover the solvent, add an appropriate amount of water to the residue, and a solid substance is precipitated, filtered, the filter cake is washed twice with water, and dried to obtain 125.1 g of oxazopyridone, with a yield of 92.0%. The melting point is 211-212°C.

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Abstract

A method for synthesizing oxazopyridone compounds relates to the field of chemical synthesis, in particular to the field of organic chemical synthesis. The method uses bistrichloromethyl carbonate and o-aminohydroxypyridine as raw materials, and the molar ratio is 0.3 to 0.7; dichloromethane, dichloroethane, chloroform, tetrachloromethane, chlorobenzene, benzene, toluene , xylene, tetrahydrofuran are solvents, and the weight ratio of solvent and bis-trichloromethyl carbonate is 1 to 10; with pyridine, dimethylformamide, triethylamine as initiator, initiator and bis-trichloromethyl carbonate The molar ratio of the ester is 0.001~1; pyridine, dimethylformamide, triethylamine, alkali metal or alkaline earth metal hydroxide or its carbonate or its bicarbonate are used as the acid-binding agent, and the acid-binding agent and The molar ratio of the bis-trichloromethyl carbonate is 6-12; at a temperature of 0-100° C., the oxazopyridone compound is obtained by stirring and reacting for 0.5-5 hours. The invention has the advantages of easy-to-obtain raw materials, safe storage and production process, simple and convenient operation, high yield, high product purity, simple post-treatment and the like.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a synthesis method of oxazopyridone compounds. Background technique [0002] Oxazolpyridone compounds are a class of important pharmaceutical and pesticide intermediates. At present, the preparation method about oxazopyridone in literature mainly contains following several kinds: [0003] (1) Adopt phosgene and o-aminohydroxypyridine to synthesize oxazopyridone, this method has adopted phosgene as carbonylation reagent, and phosgene is a highly toxic gas, difficult to operate, and phosgene can only be produced and used at a fixed point, Therefore, it is difficult to promote the use of this law to general enterprises; [0004] (2) Adopting CO and o-aminohydroxypyridine to synthesize oxazopyridone, this method is owing to adopting CO to synthesize under high pressure, so the requirement to equipment is very high; [0005] (3) adopting carbonyldiimidazole and o-aminohydroxypyrid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/04C07D221/00C07D263/00
Inventor 吴茂祥高冬寿
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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