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3-alkylthio isothiazole derivative and synthesis method thereof

A technology of isothiazole and alkylthio, which is applied in the field of 3-alkylthioisothiazole derivatives and their synthesis, can solve the problems of complex synthesis steps, low reaction yield, harsh conditions, etc., and achieve low cost and high product yield High, mild effect

Pending Publication Date: 2022-05-13
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above method needs to face complex synthesis steps, harsh conditions, low reaction yield, and a certain amount of iodine simple substance, which limits its application in the synthesis of 3-alkylthioisothiazole derivatives

Method used

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  • 3-alkylthio isothiazole derivative and synthesis method thereof
  • 3-alkylthio isothiazole derivative and synthesis method thereof
  • 3-alkylthio isothiazole derivative and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]

[0040] In the glove box, successively weigh 1-methylthio-1-benzylamine-1-butene-3-phenyl-3-thione 2a (0.3mmol), m-chloroperoxybenzoic acid (0.60mmol) in Into a 25 mL Schlenk reaction flask, under nitrogen, add 2 mL of toluene, and put it in an oil bath at 60° C. for 2 hours to react. After the reaction, the mixture was cooled to room temperature, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=20:1 ), to obtain the yellow liquid target product 1a (50mg, yield 80%). The target product was confirmed by NMR spectroscopy.

[0041] Compound Characterization Data

[0042] 3-Methylthio-5-phenylisothiazole derivative (1a), yellow liquid. 1 H NMR (400MHz, CDCl 3 )δ7.55(dd,J=7.7,2H,1.8Hz),7.42(m,3H),7.15(s,1H),2.69(s,3H). 13 C{ 1 H}NMR (100MHz, CDCl 3 )δ167.57, 163.97, 130.66, 129.80, 129.28, 126.63, 118.17, 14.17.

Embodiment 2

[0044]

[0045] In the glove box, weigh 1-methylthio-1-benzylamine-1-butene-3-m-bromophenyl-3-thione 2b (0.3mmol), m-chloroperoxybenzoic acid (0.60mmol ) into a 25mL Schlenk reaction flask, under nitrogen, add 2mL of toluene, and put it in an oil bath at 60°C for 2 hours to react. After the reaction, the mixture was cooled to room temperature, and the volatile components were removed under reduced pressure, and then separated by silica gel column chromatography (eluent was petroleum ether (60-90°C) / ethyl acetate, v / v=20:1 ), to obtain the yellow liquid target product 1b (65 mg, yield 75%). The target product was confirmed by NMR spectroscopy.

[0046] Compound Characterization Data

[0047] 3-Methylthio-5-m-bromophenylisothiazole derivative (1b), yellow liquid. 1 H NMR (400MHz, CDCl 3 )δ7.69(t,J=1.8Hz,1H),7.52(m,1H),7.46(m,1H),7.29(m,1H),7.13(s,1H),2.68(s,3H). 13 C{ 1 H}NMR (100MHz, CDCl 3 ) 165.76, 164.31, 132.69, 132.62, 130.82, 129.54, 125.33, 123.36, 118.85, 14.22...

Embodiment 3

[0049] Reaction steps and operation are with embodiment 1, and difference with embodiment 1 is, the m-ClC of 2a and 6 h 4 CO 2 The OH molar ratio is 1:1.5. The reaction was stopped, and the target product 1a (43 mg, yield 70%) was obtained after post-processing.

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Abstract

The invention discloses a 3-alkylthio isothiazole derivative and a synthesis method thereof. According to the method, alpha-thiocarbonyl-N, S-ketene is taken as a starting material, peroxy acid is taken as an accelerant, a 3-alkylthio isothiazole ring is constructed in one step, a series of 3-alkylthio isothiazole derivatives are generated, and the obtained 3-alkylthio isothiazole derivatives have certain potential pharmaceutical activity. The method only needs one-step reaction, raw materials are easy to obtain, operation is easy and convenient, synthesis reaction conditions are mild, and reaction efficiency is high.

Description

technical field [0001] The invention relates to a 3-alkylthioisothiazole derivative and a synthesis method thereof, belonging to the technical field of chemical organic synthesis. Background technique [0002] 3-Alkylthioisothiazole derivatives are a class of compounds with a wide range of biological activities, which can be used as central nervous system tranquilizers, drugs, herbicides, moth-proofing agents, preservatives, fungicides, etc. Therefore, it is of great significance to develop new methods for the synthesis of 3-alkylthioisothiazole derivatives. At present, there are many methods for the preparation of 3-alkylthioisothiazole derivatives, but the literature reports on the synthesis of 3-alkylthioisothiazole derivatives using α-thiocarbonyl-N,S-ketal as raw materials are only 1 species. The relevant preparation method is as follows: α-thiocarbonyl-N, S-ketene reacts with iodine element first to form isothiazole five-membered ring iodide salt; then reacts with po...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D275/03C07D417/04
CPCC07D275/03C07D417/04
Inventor 余正坤林杰
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI