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A kind of method for synthesizing sulfentrazone intermediate and sulfentrazone

A technology of sulfentrazone and intermediates, applied in the field of synthesis of organic fluorine compounds, can solve problems affecting product quality or yield, generation of formamide impurities, poor atom economy, etc., to achieve high product quality, less side reactions, The effect of mild reaction conditions

Active Publication Date: 2017-04-19
ORIENTAL LUZHOU AGROCHEM +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are many problems in this process, such as excessive triethylamine or pyridine to produce a large amount of waste water; consumption of 2 equivalents of methanesulfonyl chloride, poor atom economy; low yield, etc.
US5990315 discloses soluble salts such as quaternary ammonium salts and quaternary phosphonium salts to catalyze sulfonylation reactions. This method solves direct sulfonylation, but the catalyst is more expensive and the yield is low
US7169952 discloses the direct sulfonylation reaction catalyzed by high-boiling amides and tertiary amines such as DMF. This method solves the problem of direct sulfonylation reaction by using cheap catalysts, but produces formamide impurities, which affects product quality or yield

Method used

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  • A kind of method for synthesizing sulfentrazone intermediate and sulfentrazone
  • A kind of method for synthesizing sulfentrazone intermediate and sulfentrazone
  • A kind of method for synthesizing sulfentrazone intermediate and sulfentrazone

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preparation example Construction

[0034] The preparation method of compound (III) comprises: using compound (II) as a raw material, reacting in an aprotic solvent under the action of compound (A) or compound (B) and a base,

[0035]

[0036] Wherein R1, R2, R3, R4 are C1-C18 alkyl or C6-C10 aryl, and R1, R2, R3, R4 are the same or different.

[0037] R1, R2, R3, R4 of the compound (A) are preferably all n-butyl groups; the molar ratio of the compound (A) to the compound (II) is preferably 0.1-1.2:1; the reaction temperature is preferably 50 ~150°C. R1, R2, R3 and R4 of the compound (B) are preferably all n-butyl, Y is preferably bromine; the molar ratio of compound B to compound (II) is preferably 0.1-1.2:1. Described alkali is alkali metal hydroxide or carbonate, and described alkali metal hydroxide is preferably potassium hydroxide, and described carbonate is preferably potassium carbonate; The mole of potassium hydroxide and compound (II) The ratio is preferably 1-1.5:1, and the molar ratio of potassiu...

Embodiment 1

[0040] Put 1-phenyl-3-methyl-1H-1,2,4-triazol-5-one (2g), toluene (40mL), and 11.6g of tetrabutylammonium hydroxide aqueous solution (content 25%) into a 100mL flask . The reaction mixture was stirred and heated to 110°C for reaction, refluxed with water, and dried under vacuum to obtain compound (III, 1-phenyl-3-methyl-1,2,4-triazol-5-one tetrabutylammonium) (4.7 g). 1HNMR (400MHz, D2O) δ7.49 (2H, d, J = 7.6 Hz), 7.36 (2H, dd, J = 7.6, 7.6 Hz), 7.18 (1H, d, J = 7.6 Hz), 2.98 (8H, t, J = 8.4 Hz), 2.03 (3H, s), 1.46 (8H, m), 1.19 (8H, m), 1.19 (8H, m), 0.80 (12H, t, J = 8.4 Hz).

Embodiment 2

[0042] Put 1-phenyl-3-methyl-1H-1,2,4-triazol-5-one (50g), toluene (300mL), and 296g of tetrabutylammonium hydroxide aqueous solution (content 25%) into a 1000mL flask. Stir the reaction mixture to heat up and react, and reflux with water, pass through difluorochloromethane at 80-90°C until the reaction is complete, remove the solvent, add water (200mL), stir, filter, and dry to obtain 1-phenyl-4-difluoromethane Ethyl-3-methyl-1H-1,2,4-triazol-5-one (60 g).

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Abstract

The invention discloses a method for synthesizing a sulfentrazone midbody and sulfentrazone. The method comprises the following steps: preparing the sulfentrazone midbody (III) from 1-phenyl-3-methyl-1H-1,2,4-triazole-5-ketone used as a raw material in an aprotic solvent in the presence of a compound (A) or a compound (B) and alkali, performing difluoro methylation to obtain a midbody (IV), performing chlorination, nitration and reduction, and further performing methyl sulfone chloride sulfonylation to obtain a final product, namely, N(2,4-difluoro-5-(4-difluoro methyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl) phenyl) sulfamide. The method has the main beneficial effects that due to an adopted catalytic hydrogenation process, the nitroreduction is not only high in chemical selectivity, but also is more environment-friendly, efficient, safe and reliable, as triphenylphosphine, polyethylene glycol or crown ether is used as a catalyst which takes the place of a conventional used catalyst such as DMF (Dimethyl Formamide) in the sulfonylation reaction, less side reaction is caused, and the yield is high. The overall process is simple and convenient, the reaction condition is gentle, the yield is high, the product quality is high, and the industrial production is facilitated.

Description

technical field [0001] The invention relates to a synthesis method of organic fluorine compounds, in particular to a method for synthesizing a sulfentrazone intermediate and a sulfentrazone. Background technique [0002] Sulfentrazone is a herbicide belonging to the class of triazolinones. The chemical name is N-(2,4-dichloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole -1-yl)phenyl)methanesulfonamide. Its chemical structural formula is shown below: [0003] [0004] 1-phenyl-4-difluoromethyl-3-methyl-1H-1,2,4-triazol-5-one (IV) is the main intermediate in the synthesis of sulfentrazone. US5438149 discloses the preparation method of the intermediate: using difluorochloromethane as the difluoromethylation reagent, potassium carbonate as the acid-binding agent, and DMF as the reaction solvent, reacting in a closed autoclave at a temperature of 160-200oC. High temperature and high pressure reaction has many disadvantages in industrial production: for ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/12
CPCC07D249/12
Inventor 史界平苏叶华俞建娣刘维王唐君李益声郭群震虞小华蔡国平陈邦池
Owner ORIENTAL LUZHOU AGROCHEM
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