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Preparation method of sulfonyl chloride compound

A compound, oxidative chlorination technology, applied in the preparation of sulfonic acid, organic chemistry, etc., can solve the problems of troublesome post-treatment process and increase of solid waste.

Pending Publication Date: 2022-05-06
DONGGUAN HEC PESTICIDES R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The method uses TCCA / BnMe 3 NCl, NCS / BnMe 3 NCl is used as the equivalent of chlorine, wherein the quaternary ammonium salt and TCCA or NCS generate available chlorine in the reaction system, thereby promoting the smooth progress of the oxidative chlorination reaction; Secondary filtration to remove chlorine-containing quaternary ammonium salts, solid waste also greatly increased

Method used

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  • Preparation method of sulfonyl chloride compound
  • Preparation method of sulfonyl chloride compound
  • Preparation method of sulfonyl chloride compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1: Preparation of pyridine-2-sulfonyl chloride

[0062]

[0063] At room temperature, add 2,2'-dithiobipyridine (1.0g, 4.54mmol), dichloromethane (30mL) and water (10mL) into a 250 mL single-necked flask, stir evenly at 0°C, and then Add TCCA (2.11g, 9.08mmol), continue stirring at 0°C for 1 hour after addition, place the reaction solution at room temperature and continue stirring, after 1 hour, TLC (thin layer chromatography) monitors [petroleum ether / ethyl acetate (v / v )=15 / 1], raw material reaction is complete. The liquid phase was separated, the liquid was separated, and the solvent was distilled off under reduced pressure to obtain 1.25 g of a colorless transparent liquid with a yield of 77%.

[0064] 1 H NMR (600MHz, CDCl 3 )δ (ppm): 8.82 (d, J = 4.5Hz, 1H), 8.16–8.05 (m, 2H), 7.72 (ddd, J = 7.1, 4.6, 1.4Hz, 1H).

[0065] LC-MS: (M+1) m / z=177.6.

Embodiment 2

[0066] Example 2: Preparation of Thiazole-2-sulfonyl chloride

[0067]

[0068] At room temperature, 2-mercaptothiazole (1.17g, 10mmol), dichloromethane (20mL) and water (2mL) were added into a 250mL two-necked flask, and after stirring at 0°C, TCCA (2.32g, 10 mmol), the reaction was moved to room temperature, and after 1 hour TLC monitoring [petroleum ether / ethyl acetate (v / v)=15 / 1], the reaction of the raw material was complete. The liquid phase was separated, and the solvent was distilled off under reduced pressure to obtain 1.63 g of a colorless transparent liquid with a yield of 89%.

[0069] 1 H NMR (600MHz, CDCl 3 )δ(ppm): 8.06(d, J=3.2Hz, 1H), 7.97(d, J=3.1Hz, 1H).

[0070] LC-MS: (M+1) m / z=184.0.

Embodiment 3

[0071] Embodiment 3: Preparation (4-chlorophenyl) methanesulfonyl chloride

[0072]

[0073] At room temperature, add 4-chlorobenzylthiol (1.59g, 10mmol), dichloromethane (20mL) and water (2mL) into a 100mL two-necked flask, stir evenly at 0°C, then add TCCA (2.3g , 10mmol), after addition, reacted at room temperature for 1 hour, monitored by TLC [petroleum ether / ethyl acetate (v / v)=10 / 1], the raw material reacted completely, stopped the reaction, left to stand at room temperature to separate layers, and poured out the supernatant , the solvent was removed under reduced pressure with a rotary evaporator, and the residue was purified by column chromatography [petroleum ether / ethyl acetate (v / v)=10 / 1] to obtain 2.06 g of a white solid, yield: 92%.

[0074] 1 H NMR (400MHz, CDCl 3 )δ (ppm): 7.46–7.39 (m, 4H), 4.83 (s, 2H).

[0075] LC-MS: (M+1) m / z=225.0.

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Abstract

The invention relates to a preparation method of a sulfonyl chloride compound, in the method, TCCA is simultaneously used as an oxidizing agent and a chlorinating agent, and a thiol compound or a disulfide compound can be quickly converted into the sulfonyl chloride compound; the preparation method of the sulfonyl chloride is safe, environment-friendly, rapid, simple, high in yield and suitable for industrial popularization.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis. Specifically, the invention relates to a preparation method of an intermediate sulfonyl chloride compound commonly used in organic synthesis. Background technique [0002] Sulfonyl chloride compound is an intermediate widely used in the fields of medicine and pesticides, and many target products can be obtained by using it as a reaction raw material. The preparation method of various sulfonyl chloride compounds is disclosed in the prior art, wherein the more common one is HCl / Cl 2 , HCl / NCS, HCl / NH 4 NO 3 / O 2 、H 2 o 2 / TiCl 4 、H 2 o 2 / SOCl 2 Wait. Despite the potential utility of these methods, various disadvantages still exist, such as the use of expensive or not readily available reagents, drastic reaction conditions, longer reaction times, more difficult to isolate by-products, and less controllable side reactions. [0003] In addition, the literature "Hojat Veisi, Alire...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/71C07D277/36C07D249/12C07C303/02C07C309/81
CPCC07D213/71C07D277/36C07D249/12C07C303/02C07C309/81
Inventor 李义涛伍阳陈伟高国良
Owner DONGGUAN HEC PESTICIDES R&D CO LTD
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