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Method for synthesizing prothioconazole and optical active body thereof and intermediate
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An optically active, prothioconazole technology, which is applied in the field of organic synthesis and achieves the effects of high yield, few by-products and good selectivity
Active Publication Date: 2016-09-21
ORIENTAL LUZHOU AGROCHEM
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Although the yield of the oxidation reaction has increased, the treatment of the three wastes containing iron is an environmental problem
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Embodiment 1
[0073] Example 1: Synthesis of 2-{2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]hydrazono}acetic acid
[0074] Add 15.5g of 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-hydrazinopropan-2-ol hydrochloride, 120mL water and 15mL acetonitrile in a 250mL reaction flask, drop Add 7.5g of 50% glyoxylic acidaqueous solution, stir at room temperature, filter after the reaction, wash with water, and dry to obtain 16.4g of solid product (99% yield). 1 H NMR (δ, CDCl 3 ):7.456-7.437(m,1H),7.405-7.386(m,1H),7.271-7.252(m,1H),7.245-7.223(m,1H),6.971-6.899(t,1H),6.781(s ,1H),3.906-3.898,3.878-3.869(dd,1H),3.547-3.519(d,1H),3.519-3.508,3.491-3.480(dd,1H),3.211-3.183(d,1H),2.506( s,2H),1.175-1.134(m,1H),0.964-0.852(m,3H); MS: m / z=330.9([M+1] + ).
Embodiment 2
[0075] Example 2: Synthesis of (2R)-2-{2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]hydrazono}acetic acid
[0076] Add 13.7g (2R)-2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-hydrazinopropan-2-ol, 100mL water and 20mL acetonitrile in a 250mL reaction flask, drop Add 7.5g of 50% glyoxylic acidaqueous solution, stir at room temperature, filter after the reaction, wash with water, and dry to obtain 15.2g of solid product (yield: 92%).
Embodiment 3
[0077] Example 3: Synthesis of (2S)-2-{2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]hydrazono}acetic acid
[0078] Add 13.7g (2S)-2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-hydrazinopropan-2-ol, 100mL water and 20mL acetonitrile in a 250mL reaction flask, drop Add 7.5 g of 50% glyoxylic acid aqueous solution, stir at room temperature, filter after the reaction, wash with water, and dry to obtain 15.0 g of solid product (yield 91%).
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Abstract
The invention discloses a method for synthesizing prothioconazole and an optical active body thereof and an intermediate. According to the method, a hydrazine compound and glyoxylic acid react to obtain a hydrazono acetic acid intermediate, and then the hydrazono acetic acid intermediate reacts with thiocyanate to obtain a prothioconazole target product. The reaction regioselectivity is good, few side products are generated, and the yield is high. The requirement for equipment is not high, and anhydrous and anaerobic operation is not needed. The process is simple, few three wastes are generated, and the method is suitable for industrial production.
Description
technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a synthesis method and an intermediate of prothioconazole and its optically active body. Background technique [0002] Prothioconazole developed by Bayer is a novel thiotriazole fungicide (US5789430A). The structure of prothioconazole compound is shown in formula 1: [0003] [0004] 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, proth...
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