Nitrogen-chlorine type chlorination agent

A chlorinated reagent, nitrogen-chlorine type technology, applied in the field of chlorinated reagent synthesis, can solve the problems of difficult storage or limitations of reaction substrates, inability to be widely used, severe reaction conditions, etc., and achieves a wide range of reaction substrates, The effect of good chlorination activity and mild reaction conditions

Inactive Publication Date: 2015-05-13
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the severe reaction conditions of these chlorination reagents, the instability of the reag

Method used

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  • Nitrogen-chlorine type chlorination agent
  • Nitrogen-chlorine type chlorination agent
  • Nitrogen-chlorine type chlorination agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add 100mL of acetonitrile, 5g of sodium hydroxide, and 10g of benzenesulfonamide into a 250mL three-neck flask, cool down to -10°C, pass in fluorine gas, and separate after the reaction is complete. The separation method is column chromatography. The chromatographic type is adsorption column chromatography, the column temperature is normal temperature (20-35°C), the adsorbent is silica gel, the eluent is petroleum ether and ethyl acetate, gradient elution, the column diameter height is 10:1, and the dry method is used. Column, dry loading, the elution rate is 1-2 drops per second. The eluent is PE:EA=10:1 (volume ratio), and the separated eluate is rotary evaporated to remove the solvent to obtain the product, which is a light yellow solid (10.2g); add the light yellow solid obtained in the previous step, 5g sodium hydroxide , Chlorine gas is passed through, and the reaction is completed and then separated, and the separation method is column chromatography. The chroma...

Embodiment 2

[0034] Add 5 mL of acetonitrile, 0.037 g of potassium carbonate, 0.04 g of the chlorination reagent, and 0.050 g of indole derivatives into a 25 mL one-necked flask, stir overnight at room temperature, and monitor the reaction by TLC. After the reaction was complete as monitored by TLC, it was separated by column chromatography. The chromatographic type is adsorption column chromatography, the chromatographic column temperature is normal temperature (20-35°C), the adsorbent is silica gel, gradient elution, the column diameter is 15:1, the dry method is packed, the dry method is added, and the elution speed is 1-2 drops per second. The eluent was PE:EA=10:1 (volume ratio), and the separated eluent was rotary evaporated to remove the solvent to obtain the chlorinated product (0.049 g, about 90% yield). The obtained chlorinated product was characterized by nuclear magnetic resonance and mass spectrometry, and the structure of the product was correct.

[0035] The reaction flow ...

Embodiment 3

[0038] Add 5 mL of acetonitrile, 0.041 g of potassium carbonate, 0.05 g of the chlorination reagent, and 0.050 g of the reaction substrate into a 25 mL single-necked flask, stir overnight at room temperature, and monitor the reaction by TLC. After the reaction was complete as monitored by TLC, it was separated by column chromatography. The chromatographic type is adsorption column chromatography, the chromatographic column temperature is normal temperature (20-35°C), the adsorbent is silica gel, gradient elution, the column diameter is 15:1, the dry method is packed, the dry method is added, and the elution speed is 1-2 drops per second. The eluent was PE:EA=15:1 (volume ratio), and the separated eluent was rotated to remove the solvent to obtain the chlorinated product (0.054 g, yield about 85-95%). The obtained chlorinated product was characterized by nuclear magnetic resonance and mass spectrometry, and the structure of the product was correct.

[0039] The reaction flow ...

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Abstract

The invention relates to a nitrogen-chorine type chlorination agent, and belongs to the field of chlorination agent synthesis. The nitrogen-chorine type chlorination agent is obtained by taking benzene sulfonamide as a substrate, introducing fluorine gas and chlorine gas to react. In the synthesis process, a commercial product is taken as a raw material, the operation is simple, the separation is easy and the yield is high. When chlorination reaction is performed, the conditions are mild, the yield is high and the reaction substrate applied range is wide. Especially, the nitrogen-chorine type chlorination agent has good chlorination activity to dicarbonyl compounds, indole compounds and nitrogen-containing heterocyclic ring compounds.

Description

technical field [0001] The chlorination reagent of the invention relates to the chlorination of organic compounds, especially has high-efficiency reactivity to dicarbonyl compounds, indole compounds and nitrogen-containing heterocyclic compounds, and belongs to the field of chlorination reagent synthesis. Background technique [0002] Chlorination reaction has a very wide range of applications in medicine, pesticide research and development, and chemical synthesis. Currently, recognized chlorination reagents include chlorine gas, phosphorus oxychloride, phosphorus pentachloride, thionyl chloride, N-chlorosuccinimide (NCS) and the like. However, due to the severe reaction conditions of these chlorination reagents, the instability of the reagent itself, the difficulty in storage or the limitation of the reaction substrate, it cannot be widely used. Contents of the invention [0003] The object of the present invention is to provide a kind of nitrogen chlorine type chlorinat...

Claims

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Application Information

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IPC IPC(8): C07C303/40C07C311/48C07B39/00C07C67/307C07C69/738C07C45/63C07C49/697C07D209/34C07D209/30C07D233/68
Inventor 杨先金路则海李青巍
Owner EAST CHINA UNIV OF SCI & TECH
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