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Preparation method of boscalid

A technology of boscalid and chloronicotinyl chloride, applied in the field of compound preparation, can solve the problems of unindustrialization, high price of o-iodoaniline, difficult recovery and the like, and achieve the effects of convenient recycling and saving catalyst cost

Active Publication Date: 2014-09-03
CHONGQING TECH & BUSINESS UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Though reduced one-step reaction, there are 2 problems, one is to use homogeneous palladium catalyst such as tetrakis (triphenylphosphine) palladium, not only recovery is difficult, but also can increase residual heavy metal palladium in the product; Recovered palladium carbon, but the high price of o-iodoaniline will also make the production cost of boscalid higher than its market price and not suitable for industrialization

Method used

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  • Preparation method of boscalid

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preparation example Construction

[0029] The raw materials and reagents used in the preparation method of the novel fungicide boscalid provided by the present invention can be purchased from the market.

[0030] The progress of the reaction was monitored by thin-layer chromatography, and the spot was detected with a UV lamp or with Ce(NH 4 ) 2 (NO 3 ) 6 (0.5g) and (NH 4 ) 6 Mo 7 o 24 4H 2 O (24.0g) in 6% H 2 SO 4 (500 mL) of a yellow solution developed. The proton nuclear magnetic resonance spectrum of reaction product is measured by Varian mercury plus400MHz nuclear magnetic resonance instrument (TMS is internal standard), and ESI mass spectrum is determined by ESQUIRE Ion Trap LC / MS liquid chromatography / mass spectrometry analysis, the mixture of the reaction end and target product The purity was analyzed by Agilent1260 high performance liquid chromatography (Kromasil C 18 Stainless steel column, 250mm×4.6mm, methanol-water mixture solvent, 65:35V / V ​​as mobile phase, flow rate 1.0mL / min, photodio...

Embodiment 1

[0032] The preparation of embodiment 1 4'-chloro-2-acetamidobiphenyl

[0033] 2-Acetamidobromobenzene (21.4g, 0.1mol), p-chlorophenylboronic acid (18.7g, 0.12mol), 10% Pd(OH) 2 / C(0.14g, 1mmol of Pd(OH) 2 ), tetrabutylammonium bromide (6g) (or other quaternary ammonium salts of the same equivalent), potassium phosphate 7 water (64g) (or other inorganic bases of the same equivalent) and DMF (or other solvents) (100mL) in the set Stir at a certain temperature, stop the reaction after TLC monitors that the reaction is complete, filter, dilute the filtrate with ethyl acetate (500mL), wash with 1M NaOH solution (300mL), and saturated brine (3×500mL), wash with After drying with anhydrous sodium sulfate, the solvent was evaporated to obtain 24.2 g of the product, with a yield of 99%. 1 H NMR (400MHz, CDCl 3 )δ8.20(d, J=6.4Hz, 1H), 7.46(d, J=6.4Hz, 2H), 7.41-7.36(m, 1H), 7.31(d, J=6.4Hz, 2H), 7.24- 7.16 (m, 2H), 6.90 (s, br, 1H, NH), 2.04 (s, 3H). ESI-MS, m / z, [M+H] + : 246.2. ...

Embodiment 2

[0040] Example 2 Pd(OH) 2 / C recycling

[0041] 2-Acetamidobromobenzene (21.4g, 0.1mol), Pd(OH) containing p-chlorophenylboronic acid (21.4g, 0.1mol), Example 1 filtered out 2 / C, tetrabutylammonium bromide (6g), K 3 PO 4 ·7H 2 O (64g) and DMF (100mL) were reacted at 125°C until the point of 2-acetamidobromobenzene monitored by TLC disappeared, and the aftertreatment was the same as above. The results are shown in Table 2.

[0042] Table 2 Pd(OH) 2 / C recycling results

[0043]

[0044]

[0045] The results in Table 2 show that the activity of the catalyst has not changed substantially in the first two cycles, that is, the Suzuki reaction can be completed after 11 hours of reaction. From the third cycle, the activity has decreased, and the reaction time needs to be increased to complete reaction. When cycling to the 6th time, it takes 14 hours to substantially complete the reaction. But in general, Pd(OH) 2 / C can be used repeatedly when synthesizing 4'-chloro-2...

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Abstract

The invention relates to the field of compound preparation, particularly a preparation method of a novel bactericide boscalid. The method comprises the following steps: in a polar aprotic solvent or high boiling solvent, carrying out Suzuki reaction on a palladium catalyst p-chlorophenylboric acid and o-acetaminobrombenzene in the presence of alkali and quaternary ammonium salt to obtain an intermediate product 4'-chloro-2-acetaminobiphenyl; and deprotecting the intermediate product in the presence of concentrated hydrochloric acid, and condensing with 2-chloronicotinoyl chloride. According to the method, the Pd(OH)2 / C is used as the catalyst to perform the Suzuki coupling reaction, and is recovered and reutilized many times; and thus, compared with the prior art, the method provided by the invention greatly saves the catalyst cost, is convenient for recovering the catalyst, and avoids using the high-cost raw material o-iodoaniline.

Description

technical field [0001] The invention relates to the field of compound preparation, in particular to a preparation method of a novel fungicide boscalid. Background technique [0002] The full name of boscalid (common name: Boscalid) is N-(4′-chloro-2-biphenyl)-2-chloro-3-pyridinecarboxamide, a new type of nicotinamide first developed by BASF in Germany Systemic fungicide, which has been registered in more than 50 countries including Europe and the United States for the control of 80 diseases on 100 crops. It is an inhibitor of succinate coenzyme Q reductase in the mitochondrial respiratory chain. It mainly controls powdery mildew and gray mold disease, sclerotinia, brown rot and root rot and many other diseases. It can be used for the control of crop-related diseases including rapeseed, grapes, fruit trees, tomatoes, vegetables and field crops. It has a unique mechanism of action, no cross-resistance with other drugs, and its safe and beneficial ecological effects and toxic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/82C07C231/12C07C233/15
CPCC07C231/12C07D213/82C07C233/15
Inventor 孙斌郭秦
Owner CHONGQING TECH & BUSINESS UNIV
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