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Simple and efficient 1-oxygen-4,5-diazepane synthetic method

A high-efficiency technology for diazepane, which is applied in the production field of phenylpyrazoline herbicide raw materials, can solve the problems of unfavorable large-scale production, the risk of explosion and high water-free requirements, and achieves easy large-scale production. The effect of large-scale production promotion, short steps and low production cost

Active Publication Date: 2018-05-11
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method requires the use of excess sodium hydride, which has strong alkalinity and high anhydrous requirements in the reaction process, and a large amount of hydrogen gas will be generated in the reaction and post-treatment, which has the risk of explosion, which is not conducive to large-scale production; in addition , the hydrazine raw material has a Boc protecting group, so after cyclization, a deprotecting group step is required, so the route is longer

Method used

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  • Simple and efficient 1-oxygen-4,5-diazepane synthetic method
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  • Simple and efficient 1-oxygen-4,5-diazepane synthetic method

Examples

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Effect test

Embodiment 1

[0017] Add 5.2g of ethylene glycol dimesylate (20mmol) and 2.6g of hydrazine sulfate (20mmol) into 25ml of DMF, under a nitrogen atmosphere, add 6g of triethylamine (60mmol), and stir at 50 degrees Celsius The reaction was carried out for 1 h, and the reaction was detected by TLC. After the reaction was complete, the reaction solution was poured into 50ml of ice water, extracted with dichloromethane (25ml*3), the organic layers were combined, dried and concentrated to obtain 1.7g of the product, with a yield of 85%. ESI-MS: 103.5[M+H] + .

Embodiment 2

[0019] Hydrazine hydrochloride was used instead of hydrazine sulfate, other operations were the same as in Example 1, and the yield was 85%.

Embodiment 3

[0021] Hydrazine acetate was used instead of hydrazine sulfate, other operations were the same as in Example 1, and the yield was 82%.

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Abstract

The invention discloses a new method for preparing 1-oxygen-4,5-diazepane easily and efficiently. The method comprises the steps that hydrazine salt and the equivalent amount of diglycol sulfonic ester are added into a solvent, then the equivalent amount of alkaline media are added, a condensation reaction is conducted, and 1-oxygen-4,5-diazepane is obtained directly; a reaction equation is as shown in a formula (2) defined in the description. The product can be used for preparing phenyl pyrazoline herbicide; compared with the method in original paper, the method has the advantages of being short in step, low in raw material cost, capable of obtaining raw materials easily, safe and mild in reaction condition, low in production cost and the like, and large-scale production popularization iseasy to achieve.

Description

technical field [0001] The invention relates to a simple and efficient method for preparing 1-oxo-4,5-diazepane, which belongs to the production method of raw materials of phenylpyrazoline herbicides such as pinoxaden. Background technique [0002] Pinoxaden is a widely used herbicide, and 1-oxo-4,5-diazepane is an important intermediate in its production. At present, the synthetic method of the disclosed 1-oxo-4,5-diazepane is to use bis-Boc hydrazine as a raw material, carry out anhydrous reaction under strong alkali conditions such as sodium hydride, and diethylene diacetate Alcohol dimethanesulfonate is cyclized, and then the Boc protecting group is removed to obtain 1-oxo-4,5-diazepane, and the reaction equation is shown in formula (1). This method requires the use of excess sodium hydride, which has strong alkalinity and high anhydrous requirements in the reaction process, and a large amount of hydrogen gas will be generated in the reaction and post-treatment, which h...

Claims

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Application Information

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IPC IPC(8): C07D273/06
CPCC07D273/06
Inventor 房雷靳秀凤
Owner SOUTHEAST UNIV
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