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Synthetic method of 1-(2-chlorophenyl)-2-(1-chlorocyclopropyl)-3-hydrazino-2-propanol hydrochloride

A technology of propanol hydrochloride and chlorocyclopropyl, applied in chemical instruments and methods, preparation of hydroxyl compounds, preparation of hydrazine, etc., can solve the problems of long reaction time, content reduction, compound instability, etc., and achieve short reaction time , Solve the effects of poor stability and reduced dosage

Pending Publication Date: 2019-11-26
XIAN MODERN CHEM RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The method has a long reaction time, needs to use a large amount of toxic reagent hydrazine hydrate solution, and also needs to consume a large amount of acetonitrile solvent for purification (US6201128 / CN1187343)
In addition, compounds with hydrazine groups are unstable, and long-term storage will lead to a continuous decrease in their content

Method used

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  • Synthetic method of 1-(2-chlorophenyl)-2-(1-chlorocyclopropyl)-3-hydrazino-2-propanol hydrochloride
  • Synthetic method of 1-(2-chlorophenyl)-2-(1-chlorocyclopropyl)-3-hydrazino-2-propanol hydrochloride

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Experimental program
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Effect test

Embodiment 1

[0017] First prepare toluene (6.5L) / 2-methyltetrahydrofuran (2.5L) mixed solvent for later use. The 50L reactor was evacuated and replaced with nitrogen twice, then at 25°C, 465g (19.4mol) of magnesium powder, 2.5g (0.01mol) of iodine, 0.81L of mixed solvent and 90g (0.056mol) of o-chlorobenzyl chloride were added, Stir at low speed until the color of iodine disappears and a little boiling occurs, that is, the reaction is initiated. Mix the remaining mixed solvent with 2.91kg (18.07mol) o-chlorobenzyl chloride, add dropwise, and finish dropping in about 4 hours. The reaction was continued at 50°C for 0.5h. Cool down to 0-5°C, add 2.64 kg (17.26 mol) of 1-chloro-1-acetylcyclopropane dropwise, and continue the reaction for 1 h after the drop is complete. Add 5% dilute hydrochloric acid dropwise to pH = 7, and separate the layers. The organic phase was washed twice with water, separated, and the organic phase was precipitated to obtain 5.07 kg of crude Grignard product. Based...

Embodiment 2

[0022] First prepare tert-butyl methyl ether (6.9L) / 2-methyltetrahydrofuran (2.3L) mixed solvent for later use. Vacuumize the 50L reactor and replace it with nitrogen twice, then add 456g (19mol) magnesium powder, 2.5g (0.01mol) iodine, 0.9L mixed solvent and 90g (0.056mol) o-chlorobenzyl chloride at 25°C, Under stirring, until the color of iodine disappears, a little boiling occurs, that is, the reaction is initiated. Mix the remaining mixed solvent with 2.91kg (18.07mol) o-chlorobenzyl chloride, add dropwise, and finish dropping in about 4 hours. The reaction was continued at 50°C for 0.5h. Cool down to 0-5°C, add 2.64 kg (17.26 mol) of 1-chloro-1-acetylcyclopropane dropwise, and continue the reaction for 1 h after the drop is complete. Add 5% dilute hydrochloric acid dropwise to pH = 7, and separate the layers. The organic phase was washed twice with water, separated, and the organic phase was precipitated to obtain 5.18 kg of crude Grignard product. Based on 1-chloro-1...

Embodiment 3

[0025] First prepare toluene (8.1L) / 2-methyltetrahydrofuran (1.8L) mixed solvent for later use. Vacuumize the 50L reactor and replace it with nitrogen twice, then add 456g (19mol) magnesium powder, 2.5g (0.01mol) iodine, 1000mL mixed solvent and 90g (0.056mol) o-chlorobenzyl chloride at 25°C, and stir at a low speed Next, when the color of iodine disappears and a little boiling occurs, the reaction starts. Mix the remaining mixed solvent with 2.91kg (18.07mol) o-chlorobenzyl chloride, add dropwise, and finish dropping in about 5 hours. The reaction was continued at 50°C for 0.5h. Cool down to 0-5°C, add 2.59 kg (16.94 mol) of 1-chloro-1-acetylcyclopropane dropwise, and continue the reaction for 1 h after the drop is complete. Add 5% dilute hydrochloric acid dropwise to pH = 7, and separate the layers. The organic phase was washed twice with water, separated, and the organic phase was precipitated to obtain 5.97 kg of crude Grignard product. Based on 1-chloro-1-acetylcyclop...

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Abstract

The invention belongs to the field of pesticide intermediate synthesis, and more specifically discloses a synthetic method of 1-(2-chlorophenyl)-2-(1-chlorocyclopropyl)-3-hydrazino-2-propanol hydrochloride. The synthetic method of 1-(2-chlorophenyl)-2-(1-chlorocyclopropyl)-3-hydrazino-2-propanol hydrochloride comprises following steps: 1-chloro-1-chloro-acetyl-cyclopropane is taken as a raw material, and is reacted with Grignard reagent-o-chlorobenzylmagnesium chloride to prepare 1-(2-chlorophenyl)-2-(1-chlorocyclopropyl)-3-chloro-2-propyl alcohol; and under alkali conditions, reaction with hydrazine hydrate is carried out, and acidifying is carried out to obtain the 1-(2-chlorophenyl)-2-(1-chlorocyclopropyl)-3-hydrazino-2-propanol hydrochloride. The synthesis method is simple and convenient in operation, and high in product yield and purity; and product is prepared into solid organic hydrochloride, so that difficult problems of hydrazino compounds such as the poor stability and difficult product purifying process are solved.

Description

technical field [0001] The invention belongs to the field of synthesis of pesticide intermediates, in particular to a synthesis method of 1-(2-chlorophenyl)-2-(1-chlorocyclopropyl)-3-hydrazino-2-propanol hydrochloride. Background technique [0002] Prothioconazole is a broad-spectrum, low-toxicity, high-efficiency triazolethione fungicide, which is mainly used to prevent and control many diseases of cereal crops, fruits and vegetables. It has the advantages of less dosage, long-lasting effect, and safety to people and the environment. In 2016, the global annual sales exceeded 850 million US dollars, ranking third among the global fungicides. The currently widely used synthetic route is the hydrazine hydrate method. This method uses 1-chloro-1-chloroacetylcyclopropane as a raw material to prepare a propanol intermediate through Grignard reaction, which is then replaced by hydrazine hydrate and ammonium thiocyanate ring. Vulcanization and vulcanization reactions to obtain the...

Claims

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Application Information

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IPC IPC(8): C07C29/40C07C33/50C07C241/02C07C243/18
CPCC07C29/40C07C241/02C07C2601/02C07C33/50C07C243/18
Inventor 李秉擘王晓峰王红星王威罗一鸣
Owner XIAN MODERN CHEM RES INST
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