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Preparation method of C-4-thio pyrazole compound

A technology for thiopyrazoles and thiol compounds is applied in the field of preparation of C-4-position thiopyrazoles, and achieves the effects of good compatibility, no solvent and no metal participation.

Active Publication Date: 2017-06-20
QUFU NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Benefits of technology

This patented process involves reacting certain chemicals together at specific temperatures for efficient production of various types of molecules that can be used to make specialized products like pesticides or pharmaceuticals. By utilizing these reactions, we have developed new methods for producing important small organic substances called catheterothiotropes (C4T). These processes are environmentally friendly, produce large amounts of product per unit time, provide excellent functionality compatible between different groups, allow easy isolations/purifications, use less harmful solvents than previous techniques, and eliminate any metallicity concerns associated therewith.

Problems solved by technology

The technical problem addressed in this patented text relates to developing new ways to efficiently create specific types of chemical substances called cathodimers, which play crucial roles in medicine development and material science. This requires exploring alternative routes towards producing certain molecules containing either selenium atom(selenanum), hydrogen atoms, or another type of atomic group involved in metabolism. Existing techniques involve complicated processes like multiple steps involving expensive starting materials, difficult purification procedures, and harsh environments during manufacturing.

Method used

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  • Preparation method of C-4-thio pyrazole compound
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  • Preparation method of C-4-thio pyrazole compound

Examples

Experimental program
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Effect test

Embodiment 1

[0033]

[0034] At room temperature, add 0.5mmol of 3-methyl-1-phenyl-5-pyrazolone, 0.6mmol of thiophenol, and 3 equivalents of the oxidant DMSO to a 15ml sealed tube equipped with a magnetic stirrer, at 60-110°C Under reaction 20-36h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was completed, the resulting solution was cooled to room temperature, 5 ml of water and 5 ml of ethyl acetate were added to the reaction solution for extraction 5 times, and the organic solvent was removed by a rotary evaporator. The residue was purified with a silica gel column (silica gel specifications: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (10:1, v / v)) to obtain the target product 3-methyl-1-phenyl -4-Phenylthio-1 H - Pyrazol-5-ol 0.103 g, yield 73%.

[0035] 1 H NMR (DMSO- d 6 , 500 MHz, ppm) δ 12.24 (s, br, 1H), 7.79 (d, 2H, J =10.0 Hz), 7.48 (t, 2H, J = 10.0 Hz), 7.28 (t, 3H, J = 10.0 Hz), 7.14-7.08 (m,3H), 2...

Embodiment 2

[0037]

[0038]At room temperature, add 0.5mmol of 3-methyl-1-phenyl-5-pyrazolone, 0.6mmol of p-cresylthiophenol, and 3 equivalents of oxidizing agent DMSO to a 15ml sealed tube equipped with a magnetic stirrer, at 60-110 Reaction at ℃ for 20-36h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was completed, the resulting solution was cooled to room temperature, 5 ml of water and 5 ml of ethyl acetate were added to the reaction solution for extraction 5 times, and the organic solvent was removed by a rotary evaporator. The residue was purified with a silica gel column (silica gel specifications: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (10:1, v / v)) to obtain the target product 3-methyl-1-phenyl -4-(4-methylphenylthio)-1 H - Pyrazol-5-ol 0.095 g, yield 64%.

[0039] 1 H NMR (DMSO- d 6 , 500 MHz, ppm) δ 12.20 (s, br, 1H), 7.78 (d, 2H, J =10.0 Hz), 7.48 (t, 2H, J = 10.0 Hz), 7.28 (t, 1H, J = 10.0 Hz...

Embodiment 3

[0041]

[0042] At room temperature, add 0.5mmol of 3-methyl-1-phenyl-5-pyrazolone, 0.6mmol of 3-methylthiophenol, and 3 equivalents of oxidant DMSO to a 15ml sealed tube equipped with a magnetic stirrer bar. React at 60-110°C for 20-36h. The progress of the reaction was monitored by TLC (Thin Layer Chromatography). After the reaction was completed, the resulting solution was cooled to room temperature, 5 ml of water and 5 ml of ethyl acetate were added to the reaction solution for extraction 5 times, and the organic solvent was removed by a rotary evaporator. The residue was purified with a silica gel column (silica gel specifications: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (10:1, v / v)) to obtain the target product 3-methyl-1-phenyl -4-(3-methylphenylthio)-1 H - Pyrazol-5-ol 0.104g, yield 70%.

[0043] 1 H NMR (DMSO- d 6 , 500 MHz, ppm) δ 7.81 (d, 2H, J = 8.0 Hz), 7.47 (t,2H, J = 8.0 Hz), 7.27 (t, 1H, J = 7.5 Hz), 7.16 (t, 1H, J = 7.5 Hz), 6...

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Abstract

The invention relates to a preparation method of a C-4-thio pyrazole compound. The C-4-thio pyrazole compound is prepared by taking dimethyl sulfoxide as an oxidizing agent and performing reaction between a pyrazolone compound and a thiol compound for 24 to 36h under the condition of 70 to 100 DEG C. Compared with a traditional synthesis method, the preparation method has the advantages of mild reaction condition, low cost, small environment pollution, high yield, good compatibility of functional groups, convenient separation and purification, and the like.

Description

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Claims

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Application Information

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Owner QUFU NORMAL UNIV
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