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Preparation method for synthesizing thiophenol compound based on sodium sulfide nonahydrate

A technology of sodium sulfide nonahydrate and compound, which is applied in the preparation of mercaptans, the formation/introduction of mercapto/thioether groups, organic chemistry, etc., can solve problems such as side reactions, and achieve low environmental pollution, high yield, and large use. Value and socio-economic benefits

Inactive Publication Date: 2017-07-04
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of method has the advantages of mild reaction conditions, high yield, and strong adaptability to functional groups, etc., but most preparation methods still require multi-step reactions, especially when synthesizing compounds with complex structures, it is easy to cause side reactions

Method used

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  • Preparation method for synthesizing thiophenol compound based on sodium sulfide nonahydrate
  • Preparation method for synthesizing thiophenol compound based on sodium sulfide nonahydrate
  • Preparation method for synthesizing thiophenol compound based on sodium sulfide nonahydrate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the preparation of 4-methylthiophenol (3a)

[0028] Put 218mg (1mmol) of 4-iodotoluene, 720.54mg (3mmol) of sodium sulfide nonahydrate, 6.35mg (0.1mmol) of copper powder, 8.4uL (0.1mmol) of ethanedithiol, and 3mL of solvent DMSO in a magnetic In a 25mL reaction tube, seal it with argon, heat and stir, and react in an oil bath at 100°C for 20 hours. After the reaction, wash the reaction liquid with NaOH solution and transfer it to a 250mL separatory funnel, extract with ether, remove the upper organic solvent, adjust the pH of the water phase to 1-3, extract with ether and wash with water, add anhydrous magnesium sulfate to the organic phase dry. Rotary evaporation under reduced pressure and column chromatography gave 120 mg of white solid product with a yield of 97%. 1 H NMR (500MHz, CDCl 3 )δ7.19(d, J=8.1Hz, 2H), 7.06(d, J=8.0Hz, 2H), 3.39(s, 1H), 2.31(s, 3H); 13 C NMR (126MHz, CDCl 3 )δ135.61, 129.85, 129.79, 126.54, 20.88.

Embodiment 2

[0029] Embodiment 2: the preparation of 3,5-dimethylthiophenol (3b)

[0030] 232mg (1mmol) of 3,5-dimethyliodobenzene, 720.54mg (3mmol) of sodium sulfide nonahydrate, 14.35mg (0.1mmol) of cuprous bromide, 8.4uL (0.1mmol) of ethanedithiol, and 3mL of solvent DMSO , placed in a 25mL reaction tube equipped with a magnet, sealed with argon, heated and stirred, and reacted in an oil bath at 110°C for 24 hours. After the reaction, wash the reaction liquid with NaOH solution and transfer it to a 250mL separatory funnel, extract with ether, remove the upper organic solvent, adjust the pH of the aqueous phase to 1-3, extract with ethyl acetate and wash with water, add anhydrous magnesium sulfate to dry. Rotary evaporation under reduced pressure and column chromatography gave 133 mg of a colorless liquid product with a yield of 96%. 1 H NMR (500MHz, CDCl 3 )δ6.92(s,2H),6.80(s,1H),3.37(s,1H),2.27(s,6H); 13 C NMR (126MHz, CDCl 3 )δ138.72, 130.09, 127.39, 126.99, 21.08.

Embodiment 3

[0031] Embodiment 3: the preparation of 4-phenylthiophenol (3c)

[0032] Put 280mg (1mmol) of 4-iodobiphenyl, 720.54mg (3mmol) of sodium sulfide nonahydrate, 7.95mg (0.1mmol) of copper oxide, 8.4uL (0.1mmol) of ethanedithiol, and 3mL of solvent DMSO in a magnetic Fill a 25mL reaction tube with argon, heat and stir, and react in an oil bath at 120°C for 20 hours. After the reaction, wash the reaction liquid with KOH solution and transfer it to a 250mL separatory funnel, extract with ether, remove the upper organic solvent, adjust the pH of the water phase to 1-3, extract with ether and wash with water, add anhydrous magnesium sulfate to the organic phase dry. Rotary evaporation under reduced pressure and column chromatography gave 180 mg of white solid product with a yield of 97%. 1 H NMR (500MHz, CDCl3 )δ7.57-7.54 (m, 2H), 7.48-7.46 (m, 2H), 7.43 (t, J = 7.7Hz, 2H), 7.37-7.33 (m, 3H), 3.49 (s, 1H); 13 C NMR (126MHz, CDCl 3 )δ140.34, 138.74, 129.80, 129.77, 128.81, 127.76, ...

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Abstract

The invention provides a preparation method for synthesizing a thiophenol compound based on sodium sulfide nonahydrate. In an inert gas protective atmosphere, substituted iodobenzene and a sulfhydrylation reagent are added into an aprotic polar solvent, then a copper salt catalyst and a ligand compound are orderly added into the solution, the mixed solution undergoes a reaction at a temperature of 90 to 120 DEG C for 12-24h, and the reaction solution is cooled to the room temperature and is acidized so that the product is obtained. The preparation method has the advantages of simple reaction conditions, good compatibility of functional groups, high yield and small environmental pollution. Thiophenol is an important intermediate for pharmaceutical chemical synthesis and has a very wide application range in fields of chemical raw materials, pesticides and medicines. The preparation method has a great use value and good social and economic benefits.

Description

technical field [0001] The invention belongs to the intermediate field of medicine and chemical industry, and relates to a preparation method for synthesizing thiophenol compounds based on sodium sulfide nonahydrate. Background technique [0002] Thiophenol compounds are widely used in the fields of drug synthesis, organic chemistry, and material chemistry, and can be used to synthesize thrombin inhibitors, fungicides, dermatitis drugs, herbicides, corrosion inhibitors, and photosensitive materials. [0003] Traditional thiophenol preparation methods include Leuckart thiophenol synthesis [R.Leuckart, J.Prakt.Chem.1890,41,179-224.], Newman-Kwart reaction [a) M.S.Newman, H.A.Karnes, J.Org.Chem. 1966, 31, 3981-3984; b) H.Kwart, E.R.Evans, J.Org.Chem.1966, 31, 410-413.], Schoenberg rearrangement [A.Schoenberg, L.Vargha, Chem.Ber.1930, 63,178-180.], diazotization of arylamine to prepare xanthate and alkaline hydrolysis [Campaigne E, Osborn S W.J.Org.Chem.1957, 22(5):561-562.], a...

Claims

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Application Information

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IPC IPC(8): C07C319/02C07C321/26C07C323/09C07C323/20C07C323/62C07B45/06
CPCC07B45/06C07C319/02C07C321/26C07C323/09C07C323/20C07C323/62
Inventor 刘亚军薛宏宇敬冰刘勇
Owner DALIAN UNIV OF TECH
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