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Improved process for preparation of intermediates

A technology of system and solvent, which is applied in the field of preparation of 2--2-[methyl]oxirane, can solve problems such as insufficient yield and unsuitable reaction conditions

Pending Publication Date: 2021-02-23
UNITED PHOSPHORUS LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Therefore, known methods for the preparation of compounds of formula (I) and compounds of formula (II) may not be suitable for large-scale production due to various reasons such as insufficient yields, reaction conditions and formation of large quantities of undesired by-products

Method used

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  • Improved process for preparation of intermediates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0107] Example 1: 2-(2-chlorobenzyl)-2-(1-chlorocyclopropyl)oxirane and 1-chloro-2-(1-chlorocyclopropyl)-3- Preparation of (2-chlorophenyl)propan-2-ol (according to the invention)

[0108] 2- A mixture of chlorobenzyl chloride (163.0 g, 1.0 mol) in toluene (230 mL) and 2-methyltetrahydrofuran (110 mL). The reaction mixture was cooled to 0°C to 10°C, and a solution of 1-chloro-1-chloroacetylcyclopropane (153 g, 0.95 mol) in 2-methyltetrahydrofuran (40 ml) and toluene (120 ml) was added dropwise thereto , and the reaction was stirred for 2 hours. The mixture of toluene and 2-methyltetrahydrofuran was concentrated under reduced pressure, and the reaction mass was cooled to 10°C. Water (350ml) was added to the reaction mass, followed by hydrochloric acid (30%, 170g), and stirred at room temperature for 3 hours. The organic layer was separated, dried and concentrated under reduced pressure to obtain 247 g of 2-(2-chlorobenzyl)-2-(1-chlorocyclopropyl)oxirane and 1-chloro-2-(1...

Embodiment 2

[0109] Example 2: 2-(2-chlorobenzyl)-2-(1-chlorocyclopropyl)oxirane and 1-chloro-2-(1-chlorocyclopropyl)-3- Preparation of (2-chlorophenyl)propan-2-ol (comparative example according to US5099040)

[0110] A mixture of magnesium flakes (17.0 g, 0.708 mol) and iodine (0.5 g) was treated with toluene (80 ml), tetrahydrofuran (20 ml) and 2-chlorobenzyl chloride (1 g, 0.006 mol) at 20°C. At 50°C to 55°C, a mixture of 2-chlorobenzyl chloride (97.0 g, 0.60 mol) in toluene (338 ml) and tetrahydrofuran (42 ml) was added dropwise thereto within 5 hours. After the addition was complete, the mixture was reacted at 50°C to 55°C for 30 minutes. The reaction mixture was cooled to 20°C, and unreacted magnesium was decanted. To the decanted reaction mixture was added 1-chloro-1-chloroacetylcyclopropane (89 g, 0.58 mol) dropwise over 45 minutes at 20°C to 30°C, and the reaction was stirred for a further 30 minutes. The reaction mixture was poured into a solution of concentrated sulfuric aci...

Embodiment 12

[0116] Embodiment 12: the preparation of prothioconazole :

[0117] Step a): 2-(2-chlorobenzyl)-2-(1-chlorocyclopropyl)oxirane and 1-chloro-2-(1-chlorocyclopropyl)-3-(2- Preparation of Chlorophenyl)propan-2-ol

[0118] Follow the method of Example 1 to prepare 2-(2-chlorobenzyl)-2-(1-chlorocyclopropyl)oxirane and 1-chloro-2-(1-chlorocyclopropyl)-3- (2-Chlorophenyl)propan-2-ol mixtures.

[0119] Step b): Preparation of 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol prepare :

[0120] A mixture of 1,2,4-triazole (431 g), potassium carbonate (861 g) in dimethylformamide (DMF) (704 g) was heated to 80°C to 85°C for 1.0 hour. To this mixture were added dropwise 1-chloro-2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)propan-2-ol and 2-(2-chlorobenzyl)-2-(1- Chlorocyclopropyl)oxirane (577 g) in DMF (450 g) and the reaction mixture was heated to 80°C to 85°C for 3 hours. The mixture was then cooled to room temperature and filtered to give a resid...

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Abstract

Disclosed herein is a process for preparation of 1-chloro-2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)propane-2-ol (compound of formula (I)) 5 and 2-(1-chlorocyclopropyl)-2-[(2-chlorophenyl)methyl]oxirane (compound of formula (II)).

Description

Technical field: [0001] The present invention relates to the preparation of intermediates of triazole fungicides. Specifically, the present invention relates to 1-chloro-2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)propan-2-ol represented by the compound of formula (I) and Preparation of the compound represented by 2-(1-chlorocyclopropyl)-2-[(2-chlorophenyl)methyl]oxirane. [0002] Background technique: [0003] Propan-2-ol derivatives of formula (I) and oxirane derivatives of formula (II) are valuable intermediates for the preparation of triazole fungicides. One such example of a triazole fungicide is prothioconazole. Prothioconazole is a sterol biosynthesis inhibitor and systemic fungicide with protective, curative, eradication and long-acting activities. [0004] US4913727 discloses that bromo-[(2-chlorophenyl)methyl]magnesium is obtained by reacting 2-chlorobenzyl bromide with magnesium flakes in diethyl ether, bromo-[(2-chlorophenyl)methyl]magnesium is further Compo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/40C07D301/26A01N43/653A01P3/00C07D249/12
CPCC07D249/12A01N43/653C07D249/08C07D301/26C07C29/40C07C2601/02C07D405/06C07C33/50C07C29/143C07D301/28A01N25/12
Inventor 桑托什·甘帕特·谢尔克塔拉提·帕雷什·维塔尔达斯加德夫·拉耶尼肯特·施洛夫维克拉姆·拉耶尼肯特·施洛夫
Owner UNITED PHOSPHORUS LTD
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