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A method for preparing 3-isopropyl-4-amino-1,2,4-triazolin-5-one

A technology of triazoline and isopropyl, which is applied in the field of pesticide synthesis, can solve the problems of low recovery rate, difficult separation, and increased equipment cost, and achieve the effects of reducing separation operations and equipment, simplifying the reaction system, and fast reaction speed

Active Publication Date: 2020-09-15
北京怡力生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] As we all know, the boiling point of dichloromethane is only 40°C, and it is rarely used in industrial production because of its high volatility and low-temperature storage. Methanol and water are miscible, and the separation is difficult, which reduces the recovery rate; The synthesis of (III) mostly uses dichloromethane or methanol as a solvent, and the synthesis of compound (IV) mostly uses toluene as a solvent, and various separation and rectification operations will occur, which will increase certain equipment costs
In terms of raw materials, compared with solid light or phosgene, the cost of carbamating reagents is higher

Method used

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  • A method for preparing 3-isopropyl-4-amino-1,2,4-triazolin-5-one
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  • A method for preparing 3-isopropyl-4-amino-1,2,4-triazolin-5-one

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] At room temperature, 44.5g (0.50mol) of isobutyric acid and 222.5g of n-butanol were put into a 500mL reaction flask, stirring was started, and 32.9g (0.525mol) of 80% hydrazine hydrate was slowly added dropwise. After the dropwise addition was completed, the temperature was raised to reflux for dehydration. When 23mL of water came out, the heating was turned off, and the temperature of the water bath was lowered to 15-20°C to obtain product 1. 50.0 g (0.50 mol) of phosgene was slowly introduced at 15-20° C. for 1 hour, and kept at this temperature for 3 hours to obtain product 2. Afterwards, 31.3g (0.50mol) of 80% hydrazine hydrate and 8.0g (0.1mol) of 50% sodium hydroxide were added, and the temperature was raised to 105-110° C. for reflux for 3 hours, and the reaction was completed. Stand for stratification, and separate the n-butanol in the upper layer. Continue to cool the lower water phase to 20-40°C, adjust the pH to 6-7 with 30% hydrochloric acid, then continu...

Embodiment 2

[0031] At room temperature, put 44.5g (0.50mol) of isobutyric acid and 133.5g of n-butanol into a 500mL reaction flask, start stirring, and slowly add 46.9g (0.75mol) of 80% hydrazine hydrate dropwise. After the dropwise addition was completed, the temperature was raised to reflux for dehydration. When 35mL of water was removed, the heating was turned off, and the temperature of the water bath was lowered to 15-20°C to obtain product 1. Slowly add 55.0 g (0.183 mol) of solid light at 15-20° C. for 1 hour, and keep the temperature for 3 hours to obtain product 2. Add 31.3g (0.50mol) 80% hydrazine hydrate and 24.0g (0.3mol) 50% sodium hydroxide afterwards, heat up to 100-105° C. and reflux for 3 hours, and the reaction ends. Stand for stratification, and separate the n-butanol in the upper layer. Continue to cool the lower water phase to 20-40°C, adjust the pH to 6-7 with 30% hydrochloric acid, then continue to cool down to 0-5°C, and continue to stir at this temperature for h...

Embodiment 3

[0034] At room temperature, 44.5g (0.50mol) of isobutyric acid and 133.5g of n-butanol were put into a 500mL reaction flask, and stirring was started, while 32.9g (0.525mol) of 80% hydrazine hydrate was slowly added dropwise. After the dropwise addition was completed, the temperature was raised to reflux for dehydration. When 23mL of water came out, the heating was turned off, and the temperature of the water bath was lowered to 10-15°C to obtain product 1. 52.5 g (0.525 mol) of phosgene was slowly introduced at 10-15° C. for 2 hours, and kept at this temperature for 3 hours to obtain product 2. Afterwards, 31.3g (0.50mol) of 80% hydrazine hydrate and 10.7g (0.1mol) of sodium carbonate were added, and the temperature was raised to 95-100° C. for reflux for 3 hours, and the reaction was completed. Stand for stratification, and separate the n-butanol in the upper layer. Continue to cool the lower water phase to 20-40°C, adjust the pH to 6-7 with 30% hydrochloric acid, then con...

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Abstract

The invention discloses a method for preparing 3-isopropyl-4-amino-1,2,4-triazoline-5-ketone. The method comprises the following steps: 1, reacting isobutyric acid and hydrazine hydrate in an n-butylalcohol solvent at the reaction temperature of 50-150 DEG C, and producing isobutyrohydrazide; 2, reacting the isobutyrohydrazide synthesized in the step 1 and phosgene or solid light and the n-butylalcohol serving as the solvent at the reaction temperature of 0-60 DEG C, and producing 2-isobutyl hydrazino-butyl formate; 3, reacting the 2-isobutyl hydrazino-butyl formate synthesized in the step 2with hydrazine hydrate in aqueous alkali at a reaction temperature of 80-120 DEG C, thereby obtaining the 3-isopropyl-4-amino-1,2,4-triazoline-5-ketone and n-butyl alcohol. According to the method disclosed by the invention, single n-butyl alcohol serves as the solvent in the whole reaction process, the intermediate process is not separated, and the method has the advantages of being simple in reaction system, high in reaction speed and less in amount of three wastes; the n-butyl alcohol can be repeatedly used; and the synthetic method has the yield of 85%.

Description

technical field [0001] The invention belongs to the field of pesticide synthesis, in particular to a method for preparing 3-isopropyl-4-amino-1,2,4-triazolin-5-one. Background technique [0002] 3-Isopropyl-4-amino-1,2,4-triazolin-5-one is a substance with very strong chemical activity, and it is commonly used in many agricultural productions as herbicides and insecticides such as amfentrazone , propylenesulfuron-methyl, sulfentrazone and pentrazone-methyl, etc., showing its wide application. [0003] The compound is usually obtained by using isobutyric acid or isobutyric hydrazide as the starting material and undergoing the following reaction. [0004] [0005] Above-mentioned method is the method firstly developed by Germany Bayer AG (Bayer AG), and its patent US5756752 and US5693821 mention, namely in toluene, isobutyric acid (I) reacts with hydrazine hydrate to generate isobutyric hydrazide (II), and then with Phosgene reacts to obtain compound (V), followed by deso...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/14
CPCC07D249/14
Inventor 王瑞陈建伟邓旭芳
Owner 北京怡力生物科技有限公司
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