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Chemical synthesis method of 3-phenyl-5-methylisoxazole-4-formyl chloride

A technology for the chemical synthesis of methylisoxazole, which is applied in the direction of organic chemistry, can solve the problems of serious equipment corrosion, difficult treatment, and large amount of waste, and achieve the effects of low equipment corrosion, high reaction yield, and good product quality

Inactive Publication Date: 2005-12-28
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this process is that it uses thionyl chloride, a relatively toxic raw material that is controlled and used internationally, and the equipment is seriously corroded. The most troublesome thing is that the amount of three wastes is large, and the treatment is difficult and expensive.

Method used

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  • Chemical synthesis method of 3-phenyl-5-methylisoxazole-4-formyl chloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] 3-phenyl-5-methyl-4-isoxazolecarboxylic acid: bis (trichloromethyl) carbonate: N, N-dimethylformamide = 1: 0.34: 0.01 (molar ratio), the amount of chlorobenzene It is 8 times the mass of 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid.

[0014] In a 500 ml four-necked flask equipped with a thermometer, a reflux condenser and a mechanical stirrer, add 100 ml of chlorobenzene, 22 grams of 99.2% 3-phenyl-5-methyl-4-isoxazolecarboxylic acid, start stirring, press Proportionally add N,N-dimethylformamide and bis(trichloromethyl)carbonate in chlorobenzene. The temperature was raised to 130°C under stirring, and the reaction was maintained at a steady reflux for 2 hours. After the reaction was completed, the chlorobenzene was recovered by distillation under reduced pressure, and finally the distillate at 153-155°C was collected at 0.667KPa. The yield was 93.6%. The purity of the product determined by high performance liquid chromatography is 99.5%.

Embodiment 2

[0016] 3-phenyl-5-methyl-4-isoxazolecarboxylic acid: bis (trichloromethyl) carbonate: N, N-dimethylformamide = 1: 0.34: 0.005 (molar ratio), the amount of chlorobenzene It is 8 times the mass of 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid.

[0017] In a 500 ml four-necked flask equipped with a thermometer, a reflux condenser and mechanical stirring, add 100 ml of reclaimed chlorobenzene, 22 g of 99.2% 3-phenyl-5-methyl-4-isoxazole formic acid, start stirring, Add N,N-dimethylformamide and bis(trichloromethyl)carbonate in chlorobenzene in proportion. The temperature was raised to 130°C under stirring, and the reaction was maintained at steady reflux for 5 hours. After the reaction was completed, chlorobenzene was recovered by distillation under reduced pressure, and finally the distillate at 153-155°C was collected at 0.667KPa. The yield was 95.1%. The purity of the product determined by high performance liquid chromatography is 99.8%.

Embodiment 3

[0019] 3-phenyl-5-methyl-4-isoxazolecarboxylic acid: bis (trichloromethyl) carbonate: N, N-dimethylformamide = 1: 0.5: 0.01 (molar ratio), the amount of chlorobenzene It is 8 times the mass of 3-(2-chlorophenyl)-5-methyl-4-isoxazolecarboxylic acid.

[0020] In a 500 ml four-necked flask equipped with a thermometer, a reflux condenser and a mechanical stirrer, add 100 ml of chlorobenzene and 22 g of 99.2% 3-phenyl-5-methyl-4-isoxazole formic acid, open After stirring, N,N-dimethylformamide was added in proportion, and then a chlorobenzene solution of bis(trichloromethyl)carbonate was added dropwise within 30 minutes at room temperature. The temperature was raised to 130°C under stirring, and the reaction was kept under steady reflux for 3 hours. After the reaction was completed, the chlorobenzene was recovered by distillation under reduced pressure, and finally the distillate at 153-155°C was collected at 0.667KPa. The yield was 96.0%. The purity of the product determined by ...

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Abstract

The chemical synthesis method of 3-phenyl-5-methyl-4-isoxazolecarboxylic acid chloride, using bis (trichloromethyl) carbonate and 3-phenyl-5-methyl-4-isoxazolecarboxylic acid as The raw material is prepared by acyl chloride reaction in organic solvent, and the product is the key intermediate of oxacillin. The synthesis method is a chemical synthesis method of 3-phenyl-5-methyl-4-isoxazolecarbonyl chloride with reasonable process, safe and reliable production, high reaction yield, low production cost and basically no three wastes.

Description

technical field [0001] The present invention relates to a kind of with bis (trichloromethyl) carbonate [bis (trichloromethyl) carbonate] to replace sulfur oxychloride or phosphorus oxychloride or phosphorus pentachloride or phosphorus trichloride and 3-phenyl-5- The chemical synthesis method of 3-phenyl-5-methylisoxazole-4-formyl chloride (3-phenyl-5-Methylisoxazole-4-carbonylChloride) by the reaction of methylisoxazole-4-carboxylic acid, 3-phenyl -5-Methylisoxazole-4-carbonyl chloride is a key intermediate of oxacillin. Background technique [0002] Before the present invention was made, the chemical synthesis method of prior art 3-phenyl-5-methyl-4-isoxazole carboxyl chloride was based on sulfur oxychloride or phosphorus oxychloride or phosphorus pentachloride or trichloride Phosphorus and 3-phenyl-5-methyl-4-isoxazole formic acid as raw materials in the reaction. As proposed in US 2996501 (1961), use 0.1 mole of 3-phenyl-5-methyl-4-isoxazole formic acid to react with 0....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D261/18
Inventor 李永曙苏为科许进
Owner ZHEJIANG UNIV OF TECH
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