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A novel sulfonyl chloride derivative, its preparation method and its application

A technology for sulfonyl chloride derivatives and compounds, applied in the field of sulfonyl chloride derivatives, can solve problems such as unfavorable synthesis of derivatives, and achieve the effect of simple steps

Active Publication Date: 2021-08-27
TAIZHOU POLYTECHNIC COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Taking the aromatic sulfonyl chloride compound of the same kind as the present invention as an example, the aromatic ring structure of the existing compound contains mostly one or two simple substituents, which is unfavorable for synthesizing more derivatives with complex structures

Method used

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  • A novel sulfonyl chloride derivative, its preparation method and its application
  • A novel sulfonyl chloride derivative, its preparation method and its application
  • A novel sulfonyl chloride derivative, its preparation method and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 Preparation of ethyl 2-(4-bromo-2-(chlorosulfonyl)phenoxy)acetate (compound I)

[0037] Step 1 Synthesis of 2-(4-bromophenoxy) ethyl acetate

[0038]

[0039] Compound 1, i.e. 4-bromophenol (3g, 17.34mmol) was dissolved in 10mL of DMF, followed by adding ethyl chloroacetate (2.55g, 20.81mmol) and potassium carbonate (7.18g, 52.02mmol), and at 80 Stir at ℃ for 3-4h.

[0040] After the reaction was complete, water was added to the mixture and stirred. The precipitated solid was suction-filtered to obtain 4.46 g of the target compound as a white solid, yield: 99.3%, and this white solid was ethyl 2-(4-bromophenoxy)acetate (compound 2).

[0041] 1 H NMR (400MHz, CDCl 3 )δ7.39(d, J=9.0Hz, 2H), 6.80(d, J=9.0Hz, 2H), 4.59(s, 2H), 4.27(q, J=7.0Hz, 2H), 1.30(t, J=7.3Hz,3H).MS(ESI)m / z calcd for C 10 h 11 BrO 3 257.98&259.98;found[M+Na] + 283.3.

[0042] Step 2 Synthesis of ethyl 2-(4-bromo-2-(chlorosulfonyl)phenoxy)acetate

[0043]

[0044] Compound 2, ...

Embodiment 2

[0047] The preparation process optimization of embodiment 2 compound I

[0048] (1) Exploration of preliminary synthesis conditions

[0049] In the field, there is currently no report on the synthesis of compound I. The present invention intends to prepare compound I by direct chlorosulfonation of chlorosulfonic acid. Preliminary studies have found that the target compound cannot be obtained by adding chlorosulfonic acid alone (Table 1, experiments 1-3). After analysis, the present invention adds thionyl chloride to the reaction system to finally obtain the target product.

[0050] It is worth noting that when using different concentrations of thionyl chloride to participate in the reaction, the reaction yield of the low-concentration thionyl chloride solution was significantly lower than that of the high-concentration thionyl chloride (Table 1, experiments No. 4 to 5), It shows that the concentration and dosage of thionyl chloride have great influence on the reaction yield...

Embodiment 3

[0065] Application of Example 3 Compound I in the Preparation of Sulfonamide, Biphenyl and Amide Derivatives

[0066] The application of compound I in the preparation of sulfonamide, biphenyl and amide derivatives is as follows: Figure 5 shown.

[0067] Here are a few applications:

[0068] (1) Compound I is used to prepare sulfonamide derivatives

[0069]

[0070] Dissolve ethyl 2-(4-bromo-2-(chlorosulfonyl)phenoxy)acetate (100mg, 0.28mmol) and n-propylamine (24.8mg, 0.42mmol) in 6mL of dichloromethane, add 0.5mL of pyridine, 40°C The reaction was carried out for 1.5 h, and the reaction was monitored by TLC. After the reaction, add 20mL of water and 3-5mL of dilute hydrochloric acid, extract with ethyl acetate (15mL×2), wash the organic layer once with water, once with saturated brine, dry over anhydrous sodium sulfate, concentrate under reduced pressure, and pass the crude product through Separation by silica gel column chromatography gave the target compound ethyl 2-...

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Abstract

The present invention provides a novel sulfonyl chloride derivative, its preparation method and application. The structural formula of the sulfonyl chloride derivative is shown in Formula I. The preparation method comprises the following steps: 1) taking compound 1, i.e. p-bromophenol as a raw material, under the catalysis of a base, in a suitable organic solvent, substituting the phenolic hydroxyl group with ethyl chloroacetate to obtain compound 2, That is, 2-(4-bromophenoxy)ethyl acetate; 2) In a suitable organic solvent, the compound 2 is chlorosulfonated on the benzene ring with chlorosulfonic acid and a chlorinating reagent to obtain the compound of formula I. This derivative and its synthesis process have not seen any domestic and foreign literature reports at present, and there is no similar product on the market. The present invention designs a brand-new synthetic route, and optimizes the conditions for the key reaction steps in the route, and determines the optimal process conditions. The new process has the characteristics of cheap and easy-to-obtain starting materials, simple steps, easy post-processing and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a novel sulfonyl chloride derivative, a preparation method and application thereof, and belongs to the technical field of organic synthesis. Background technique [0002] Sulfonyl chloride is an important "organic synthesis building block". As a kind of sulfur-containing organic reagent with a wide range of sources and cheap and easy access, it can react with nucleophiles such as amines and alcohols to construct S-N bonds and S-O bonds to obtain the corresponding sulfonamides. , sulfonic acid or sulfonic acid ester derivatives are widely used in the synthesis of medicine and materials. Sulfonyl chlorides can be divided into aliphatic sulfonyl chlorides and aromatic sulfonyl chlorides. Among them, arylsulfonyl chloride is an important intermediate in the synthesis of sulfonamide drugs, dyes, and pesticides. [0003] Although a variety of sulfonyl chloride derivatives are already on the market, most of these sulfonyl chlorides ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/87C07C303/08C07C67/31C07C69/708C07C303/38C07C311/29
CPCC07C67/31C07C303/08C07C303/38C07C309/87C07C69/708C07C311/29
Inventor 张茂风王昌铭刘竺云胡清清
Owner TAIZHOU POLYTECHNIC COLLEGE
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