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Preparation method of N,O-dimethyl-N'-nitroisourea

A technology of nitroisourea and dimethyl, which is applied in the field of preparation of N,O-dimethyl-N'-nitroisourea, can solve the problem of low reaction yield, achieve simple operation and suppress side reactions , the effect of increasing the reaction yield

Active Publication Date: 2014-07-30
湖南海利常德农药化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] During the synthesis of N,O-dimethyl-N'-nitroisourea by the above two methods, a large amount of by-product methylguanidine is generated (about 25%), which is an important reason for the low yield of the reaction

Method used

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  • Preparation method of N,O-dimethyl-N'-nitroisourea

Examples

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Effect test

Embodiment 1

[0016] In a 250mL three-necked bottle equipped with mechanical stirring and a thermometer, add 24.3g (200mmol) of 98% O-methyl-N-nitroisourea, 13.5g (200mmol) of methylamine hydrochloride, 97.2ml Tap water and 19.0g (200mmol) potassium fluoride were reacted at 15°C for 2 hours. After the reaction was completed, the product was cooled to 0°C and filtered. The product was washed with 20mL of tap water at 5°C and dried to obtain 20.2g of a white product. The liquid chromatography quantification was 99.3 %, the yield is 75.4% based on O-methyl-N-nitroisourea.

Embodiment 2

[0018] In a 250mL three-necked flask equipped with mechanical stirring and a thermometer, add 24.3g (200mmol) of 98% O-methyl-N-nitroisourea, 27.0g (400mmol) of methylamine hydrochloride, 97.2ml Tap water and 57.0g (600mmol) potassium fluoride were reacted at 35°C for 2 hours. After the reaction was completed, cooled to 0°C and filtered, the product was washed with 20mL of tap water at 5°C, and dried to obtain 21.1g of a white product. The liquid chromatography quantification was 99.5 %, the yield is 78.9% based on O-methyl-N-nitroisourea.

Embodiment 3

[0020] In a 250mL three-necked flask equipped with a mechanical stirrer and a thermometer, add 24.3g (200mmol) of 98% O-methyl-N-nitroisourea, 20.3g (200mmol) of methylamine hydrochloride, 97.2ml Tap water and 38.0g (400mmol) potassium fluoride were reacted at 25°C for 5 hours. After the reaction was completed, cooled to 0°C and filtered, the product was washed with 20mL of tap water at 5°C, and dried to obtain 21.2g of a white product. The quantitative value of liquid chromatography was 99.2 %, the yield is 79.1% based on O-methyl-N-nitroisourea.

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Abstract

The invention discloses a preparation method of N,O-dimethyl-N'-nitroisourea. According to the preparation method, O-methyl-N-nitroisourea and methylamine hydrochloride are used as a raw material, and water is used as a solvent, so that reaction is performed in a potassium fluoride-water system, wherein the chemical reaction formula is as shown in the specification. The preparation method disclosed by the invention is simple and convenient in process and simple in operation; the water is used as the solvent, the pH value is not needed to be regulated and a catalyst is not needed to be added, so that the generation of secondary reactions can be effectively inhibited. The purity of products can reach more than 99%, and the yield can reach 79.1%; the preparation method is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of N, O-dimethyl-N'-nitroisourea. Background technique [0002] N,O-dimethyl-N'-nitroisourea is a key intermediate for the preparation of dinotefuran, a compound with the following general formula: [0003] [0004] At present, the preparation methods of N, O-dimethyl-N'-nitroisourea reported in literature both at home and abroad are as follows: [0005] 1. Using O-methyl-N-nitroisourea and methylamine hydrochloride as raw materials, continuously adjust the pH to 8 with 1% sodium hydroxide, pass through the column and crystallize to obtain N,O-dimethyl- N'-nitroisourea, yield 59.6%. This method needs to adjust the pH value accurately, and the post-treatment is complicated and the yield is low. Its synthesis method is as follows: [0006] [0007] 2. Using O-methyl-N-nitroisourea and methylamine hydrochloride as raw materials, react at 20°C for 16 hours in aqueous solution of sodium chloride with s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C275/70C07C273/18
Inventor 罗亮明黄超群杜升华熊莉莉胡志彬孔晓红
Owner 湖南海利常德农药化工有限公司
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