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Intermediate compound, and synthetic method of prothioconazole

A technology of prothioconazole and synthetic method, which is applied in the field of organic synthesis, can solve problems such as yield decline, and achieve the effects of avoiding post-processing, high conversion rate and selectivity, and cheap and easy-to-obtain synthetic raw materials

Active Publication Date: 2017-05-31
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method solves the dangerous problem of using n-BuLi reagent, but this technical scheme still needs anhydrous anaerobic and ultra-low temperature reaction equipment and conditions, needs to use Grignard reagent greater than two equivalents simultaneously, and productive rate drops significantly (from n- BuLi's 93% drops to 68%)

Method used

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  • Intermediate compound, and synthetic method of prothioconazole
  • Intermediate compound, and synthetic method of prothioconazole
  • Intermediate compound, and synthetic method of prothioconazole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthesis of 2-(1-chlorocyclopropyl)-3-chloro-1-(2-chlorophenyl)-2-propanol

[0051] In a 250mL round-bottomed three-neck flask device with a constant pressure titration funnel and a condenser tube, anhydrous and anaerobic operations were carried out under nitrogen protection conditions, and 10g (0.062mol) of 2-chlorobenzyl and 50mL of THF solution were mixed and placed in a constant pressure drop In the funnel, add 1.8g (0.074mol) of magnesium chips, 10ml of THF solution and a small amount of iodine into the three-necked flask, drop in 2ml of THF solution of 2-chlorobenzyl chloride, trigger with slight heat, put the device into the ice bath and slowly Add dropwise (drop / 3s) until the drop is over, and then react for 1 h after the drop is over, slowly drop the above Grignard reactant into THF (30mL) of 9.0g (0.058mol) 1-chloro-1-chloroacetylcyclopropane The solution was slowly added dropwise (drop / 3s) until the drop was completed, and the reaction was continued for 1 ho...

Embodiment 2

[0053] Synthesis of Prothioconazole

[0054] Synthesis of compound (Ⅳ)

[0055] Dissolve 5g (0.072mol) of 1,2,4-triazole in 15ml of DMF, add 6.9g (0.216mol) of sublimed sulfur, heat to 140°C, react for 3.5h, cool to room temperature, filter, and use the filtrate Wash with saturated sodium chloride, extract with ethyl acetate, separate the organic phase, dry over anhydrous sodium sulfate, distill off the ethyl acetate to obtain 6.95 g of solid compound (IV), with a yield of 95%.

[0056] Synthesis of compound (Ⅴ)

[0057] 3.03g (30mmol) of compound (Ⅳ) was dissolved in 30mL DCM, and 2.37g (30mmol) of redistilled pyridine was added. Under ice-bath stirring conditions, 2.64g (15mmol) benzenesulfonyl chloride was added dropwise, and the dropwise addition was completed in about 1 hour. Remove the ice-water bath and stir at room temperature for 5h. DCM was evaporated, and 15 mL of water and 10 mL of ethyl acetate were added to the residue, reacted for 1 h, filtered, and washed w...

Embodiment 3

[0085] Synthesis of compound (Ⅵ)

[0086] Stir and mix 6g (30mmol) of compound (Ⅴ), 30ml of DMF, and 12.42g (90mmol) of potassium carbonate, and heat to 60°C. 17.61 g (63 mmol) of compound (II) was added dropwise, and the dropwise addition was completed after 2 hours. The reaction was continued, stopped, and cooled to room temperature. Suction filtration, the filtrate was washed with saturated brine, extracted with ethyl acetate, the organic phase was washed three times with saturated brine, the organic phase was separated, dried over anhydrous sodium sulfate, and the product obtained by rotary evaporation. 17.31 g of compound (VI) was obtained with a yield of 84%.

[0087] Synthesis of Target Compound (Ⅶ) Prothioconazole

[0088] Dissolve 6.25g (0.009mol) of compound (Ⅵ) in 30ml of methanol, add 1.21g (0.019mol) of metal Zn, stir and react at 40°C for 3h, stop the reaction, directly recrystallize, precipitate the crystals and filter to obtain the target compound (Ⅶ) Prothi...

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Abstract

The invention discloses an intermediate compound, and a synthetic method of prothioconazole. The method comprises the following steps: carrying out a substation reaction on 5,5'-dithio-bis(1,2,4-triazole) and 2-(1-chlorocyclopropyl)-3-chloro-1-(2-chlorophenyl)-2-propanol to obtain the key intermediate compound; and reducing the key intermediate compound to obtain the target product prothioconazole. The synthetic method has the advantages of high conversion rate, high selectivity, cheap and easily available synthesis raw materials, reduction of the production cost, mild and easily controlled technologic reaction conditions, simplicity in operation, easiness in product purification, obtaining of the product through direct re-crystallization, simple and accurate control method of intermediates in all steps, high product yield, good atom economy, avoiding of tedious post-treatment, large competition advantages and industrial production utilization values, avoiding of strong alkalis and other raw materials, extremely low three wastes, and according with the green chemistry idea.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthetic method of an intermediate compound and prothioconazole. Background technique [0002] Prothioconazole is a demethylation inhibitor (DMIs), and its mechanism of action is to inhibit the demethylation reaction of l4-position of lanosterol, the precursor of sterol in fungi. Prothioconazole not only has good systemic activity, excellent protection, treatment and eradication activities, but also has a long duration. The results of a large number of field efficacy tests show that prothioconazole not only has good safety for crops, but also has a good effect on disease prevention and treatment, and has a significant increase in yield. Compared with triazole fungicides, prothioconazole has a broader spectrum Bactericidal activity. [0003] Prothioconazole is currently mainly used to prevent and control many diseases of cereal crops such as wheat, barley, rape, p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 苏贤斌刘李徐萧和程杰
Owner NANJING TECH UNIV
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