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A kind of halosulfur compound and its preparation method and application

A technology of sulfur compounds and compounds, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., can solve problems such as production hazards, achieve short reaction time and mild reaction conditions , the effect of high yield

Active Publication Date: 2016-01-13
ORIENTAL LUZHOU AGROCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method can shorten the reaction time and increase the yield, chlorine gas is needed in the catalyst preparation process, which has great danger in production.

Method used

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  • A kind of halosulfur compound and its preparation method and application
  • A kind of halosulfur compound and its preparation method and application
  • A kind of halosulfur compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Preparation of N-[(1-chloro)-thiocyclobutyl]-succinimide

[0065] 13.3g of N-chlorosuccinimide was dissolved in 50ml of dichloromethane, stirred and cooled to 15°C, and 8.8g of tetrahydrothiophene was added to the reaction system. Stir the reaction for 30 minutes, remove the solvent, and dry to obtain about 17.5 g of the title compound N-[(1-chloro)-thiocyclobutyl]-succinimide.

[0066] NMR (CDCl 3 )δ: 1 H:1.94(t,4H),2.77(s,4H),2.83(t,4H).

Embodiment 2

[0068] Preparation of N-[(1-bromo)-thiocyclobutyl]-succinimide

[0069]17.8g of N-bromosuccinimide was dissolved in 50ml of dichloromethane (10ml) and dichloroethane (40ml) mixed solvent, stirred and cooled to 15°C, and 8.8g tetrahydrochloride was added to the reaction system Hydrothiophene was reacted with stirring for 30 min, and the solvent was removed to obtain 22.5 g of the title compound N-[(1-chloro)-thiocyclobutyl]-succinimide.

[0070] NMR (CDCl 3 )δ: 1 H:2.13(t,4H),2.76(s,4H),3.12(t,4H).

Embodiment 3

[0072] Preparation of N-[(1-bromo)-thiodimethyl]-succinimide

[0073] In a 500ml three-neck flask, add 89g of N-bromosuccinimide and 150ml of dichloromethane, stir and cool to 20°C, and add 31g of dimethyl sulfide into the reaction system. The reaction was stirred for 1 h, and the solvent was removed to obtain 99.5 g of the title compound N-[(1-chloro)-thiodimethyl]-succinimide.

[0074] NMR (CDCl 3 )δ: 1 H:2.77(s,4H),2.97(s,6H).

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Abstract

The present invention relates to a halogenated sulfur compound such as N-[(1-halogenated)-thiocyclobutyl]-succinimide and preparation method thereof. Disclosed is a catalytic application of such compounds in the reaction of sulfuryl chloride and organic amine to prepare sulfonamide. The disclosed catalytic reaction for preparing sulfonamide by the halogenated sulfur compounds requires a mild reaction condition and a short reaction time, and has a high yield. The present invention does not need to use hazardous chlorine gas, thus being safe and environmentally friendly, and has great application value.

Description

technical field [0001] The invention relates to the synthesis of organic sulfur compounds, especially the synthesis of halogenated sulfur compounds, and their use in the reaction of aromatic sulfonyl chlorides, heteroaromatic sulfonyl chloride compounds, aromatic amines, and heteroaromatic amine compounds to prepare sulfonamides Catalytic applications. Background technique [0002] The method for preparing sulfonamides by reacting aromatic sulfonyl chlorides and heteroaromatic sulfonyl chloride compounds with aromatic amines and heteroaromatic amine compounds cannot obtain satisfactory results in many cases because the reaction is slow and the yield is poor. Especially when aromatic sulfonyl chlorides, heteroaromatic sulfonyl chloride compounds and aromatic amines, heteroaromatic amine compounds contain one or two ortho substituents, the results are often unsatisfactory due to the stereoelectronic effect of the ortho substituents . WO98 / 21178 discloses a class of N-arylsul...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/48C07D233/82C07D209/48B01J31/02C07D487/04C07D249/12
CPCC07D207/48C07D209/48C07D233/82C07D249/12C07D487/04C07D409/04
Inventor 赖玉龙胡俊铎高峰郭群震虞小华蔡国平江海毛文聪陈邦池
Owner ORIENTAL LUZHOU AGROCHEM