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Preparation method and purification method of heterocyclic nitrogen sulfide

A technology of sulfide and nitrogen heterocycle, applied in the field of preparation of nitrogen-containing heterocycle sulfide, can solve problems such as unfavorable industrialization popularization, complex cobalt complex, expensive structure, etc., and achieves cheap synthesis system, simple process flow and cost low effect

Active Publication Date: 2018-02-16
WENZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The above-mentioned synthesis method has the advantage of high synthesis efficiency, but this method requires an expensive cobalt complex with a complex structure, and an equivalent amount of oxidant and additives, so the cost of using the above-mentioned synthesis method is high, which is not conducive to industrialization and popularization

Method used

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  • Preparation method and purification method of heterocyclic nitrogen sulfide
  • Preparation method and purification method of heterocyclic nitrogen sulfide
  • Preparation method and purification method of heterocyclic nitrogen sulfide

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specific Embodiment 1

[0031] Specific Example 1: The substrate is N-pyridylpyrrole and diphenyl disulfide molar ratio is 1:2, the molar percentage of cuprous iodide and N-pyridylpyrrole is 10%, and the ligand is 2-bicyclic Hexylphosphonium-2,4,6-triisopropylbiphenyl, the molar percentage of ligand and N-pyridylpyrrole is 10%, and the reaction temperature is 120°C;

[0032] 28.8 mg (0.2 mmol) N-pyridyl pyrrole, 87.3 mg (0.4 mmol) diphenyl disulfide, 3.8 mg (0.02 mmol) cuprous iodide, 9.6 mg (0.02 mmol) 2-dicyclohexylphosphorus-2 , Add 4,6-triisopropylbiphenyl into the reaction test tube, then add 2mL dimethyl sulfoxide, react at 120°C for 24 hours, cool after the reaction, filter, spin the filtrate, remove the solvent, and use silica gel Column chromatography, petroleum ether washing, TLC detection, combined effluent containing product, rotary evaporator distillation to remove solvent, vacuum drying to obtain light yellow oily liquid N-pyridyl-2,5-diphenylthiopyrrole, yield 81%. 1 HNMR (500MHz, CD...

specific Embodiment 2

[0033] Specific embodiment 2: variable is that the mole percent of cuprous iodide and substrate I is 20mol%;

[0034] 28.8 mg (0.2 mmol) N-pyridyl pyrrole, 87.3 mg (0.4 mmol) diphenyl disulfide, 7.6 mg (0.04 mmol) cuprous iodide, 9.6 mg (0.02 mmol) 2-dicyclohexylphosphorus-2 , Add 4,6-triisopropylbiphenyl into the reaction test tube, then add 2mL dimethyl sulfoxide, react at 120°C for 24 hours, cool after the reaction, filter, spin the filtrate, remove the solvent, and use silica gel Column chromatography, petroleum ether washing, TLC detection, combined effluent containing product, rotary evaporator distillation to remove solvent, vacuum drying to obtain light yellow oily liquid N-pyridyl-2,5-diphenylthiopyrrole, yield 68%.

specific Embodiment 3

[0035] Specific embodiment 3: variable is that the mole percent of cuprous iodide and substrate I is 15mol%;

[0036] 28.8 mg (0.2 mmol) N-pyridyl pyrrole, 87.3 mg (0.4 mmol) diphenyl disulfide, 5.7 mg (0.03 mmol) cuprous iodide, 9.6 mg (0.02 mmol) 2-dicyclohexylphosphorus-2 , Add 4,6-triisopropylbiphenyl into the reaction test tube, then add 2mL dimethyl sulfoxide, react at 120°C for 24 hours, cool after the reaction, filter, spin the filtrate, remove the solvent, and use silica gel Column chromatography, petroleum ether washing, TLC detection, combined effluent containing product, rotary evaporator distillation to remove solvent, vacuum drying to obtain light yellow oily liquid N-pyridyl-2,5-diphenylthiopyrrole, yield 73%.

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Abstract

The invention discloses a preparation method and a purification method of heterocyclic nitrogen sulfides. The preparation method includes the steps: taking N-pyridyl pyrrole or pyridyl indole and disulfide ether as substrates, taking dimethyl sulfoxide as solvents, performing heating reaction on the N-pyridyl pyrrole or pyridyl indole, the disulfide ether and the dimethyl sulfoxide under catalysisof transition metal copper salt and the action of a ligand in the air environment to prepare crude products, and performing filtration and solvent removal on the crude products to obtain remainders;performing silica column chromatography on the remainders, spraying and washing the remainders by the aid of eluting liquid, collecting effluents, combining the effluents containing products, performing concentration and solvent removal on the combined effluents, and performing vacuum drying to obtain a target product. The preparation method has the advantages of simple technological process, lowcost and high yield.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a preparation method of nitrogen-containing heterocyclic sulfides and a purification method thereof. Background technique [0002] Nitrogen heterocyclic sulfides are an important class of organic compounds with good biological activities, such as insecticidal, bactericidal, herbicidal, anti-tumor and anti-hypertensive, etc., and have played an increasingly important role in the fields of medicine and pesticides. And show good development prospects. [0003] Literature Tobias et al. (Angew.Chem.Int.Ed.2016,55,11287-11291.) discloses the synthesis of azepines by the cobalt-catalyzed reaction of N-pyrimidinyl indole with benzenethiol and diphenyl disulfide Episulfide, the method thereof comprises a preparation process and a purification process. [0004] 1. The preparation process is as follows: [0005] Take N-pyrimidinyl indole as substrate (0.5mmol), add benzenethiol...

Claims

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Application Information

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IPC IPC(8): C07D401/04
CPCC07D401/04
Inventor 邓辰亮张兴国张小红徐薇
Owner WENZHOU UNIVERSITY
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