Preparation method of 4-thio-pyrazolone derivative

A technology of pyrazolone and derivatives, applied in the field of organic synthesis, can solve the problems of low yield, poor substrate applicability, difficult operation, etc., and achieve the effect of easy-to-obtain and cheap raw materials

Inactive Publication Date: 2016-07-13
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above-mentioned method or substrate applicability is poor, or yield is low, or reactant is sensitive to air and water and is difficult to operate, is unfavorable for reaction.

Method used

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  • Preparation method of 4-thio-pyrazolone derivative
  • Preparation method of 4-thio-pyrazolone derivative
  • Preparation method of 4-thio-pyrazolone derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0064] Add 1,3-dimethylpyrazolone (0.5mmol), 4-methylbenzenesulfonyl chloride (0.6mmol), KI (0.1mmol), and triphenylphosphine (1.0mmol) in sequence in a 15mL pressure-resistant tube and 1,4-dioxane (1 mL), then heated to 80 o C reaction, after spotting the plate to detect the completion of the reaction, gradient elution was carried out by dichloromethane:methanol volume ratio of 40:1–20:1. A white solid was obtained in 85% yield. NMR data: 1 HNMR (400MHz, d6 DMSO)δ11.29(s,1H),7.06(d,J=8.0Hz,2H),6.89(d,J=7.6Hz,2H),3.48(s,3H),2.22(s,3H),1.98 (s,3H)

[0065]

Embodiment 2

[0067] Add 1,3-dimethylpyrazolone (0.5mmol), 4-methoxybenzenesulfonyl chloride (0.6mmol), KI (0.1mmol), triphenylphosphine (1.0mmol ) and 1,4-dioxane (1 mL), then heated to 60 oC reaction, spot plate detection After the reaction is complete (the reaction time is 8-24 hours), the gradient elution is carried out by dichloromethane: methanol volume ratio of 40:1-20:1. A pale yellow solid was obtained with a yield of 83%. NMR data: 1 HNMR (400MHz, d6 DMSO) δ11.32(s,1H),6.98(s,2H),6.86(s,2H),3.70(s,3H),3.47(s,3H),2.00(s,3H).

[0068]

Embodiment 3

[0070] Add 1,3-dimethylpyrazolone (0.5mmol), 4-cyanobenzenesulfonyl chloride (0.6mmol), KI (0.1mmol), and triphenylphosphine (1.0mmol) in sequence in a 15mL pressure-resistant tube and 1,4-dioxane (1 mL), then heated to 100 o C reaction, spot plate detection After the reaction is complete (the reaction time is 8-24 hours), the gradient elution is carried out by dichloromethane: methanol volume ratio of 40:1-20:1. A white solid was obtained in 96% yield. NMR data: 1 HNMR (400MHz, d6 DMSO)δ11.58(s,1H),7.70(d,J=8.4Hz,2H),7.13(d,J=8.4Hz,2H),3.52(s,3H),1.98(s,3H)

[0071]

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Abstract

The invention discloses a preparation method of a 4-thio-pyrazolone derivative. According to the method, a pyrazolone derivative is directly applied to react with sulfonyl chloride in the presence of potassium iodide and triphenylphosphine to synthesize the 4-thio-pyrazolone derivative, wherein the used solvent is 1,4-dioxane, the reaction temperature is 60-100 DEG C, and the reaction time is 8-24 hours; and gradient elution is carried out on dichloromethane and methanol as a mobile phase at the volume ratio of (40 to 1) to (20 to 1) to obtain a white or light yellow solid. A series of thio-pyrazolone compounds are synthesized by the novel method for the first time, and can be used as important medical intermediates of analgesic medicines, antipyretic medicines and antibacterial medicines.

Description

[0001] This patent is funded by the National Natural Science Foundation of China (funding number: 21572158). technical field [0002] The invention belongs to the technical field of organic synthesis, and relates to an organic synthesis method for synthesizing thiopyrazolone compounds through the cross-coupling reaction of pyrazolone derivatives and arylsulfonyl chlorides. Especially the preparation method of 4-position thio pyrazolone derivatives. Background technique [0003] Pyrazolone is an important five-membered heterocyclic ring, which is commonly found in biologically active natural products and drugs. It can be used as analgesic, antipyretic, antibacterial, etc., and has good biological activity and medicinal value. It has attracted the attention of scientists from all over the world. [0004] Currently, there are three methods for synthesizing thiopyrazolone compounds. One method is the substitution reaction of phenyl sulfide chlorine and pyrazolone. The second m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/20C07D231/22
CPCC07D231/20C07D231/22
Inventor 赵霞卢晓宇芦逵
Owner TIANJIN NORMAL UNIVERSITY
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