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Preparation method of sulfonyl azide compounds

A technology for sulfonyl azide compounds, applied in the field of preparation of sulfonyl azide compounds, to achieve the effects of safe and controllable operation, mild process conditions, and easy industrial production

Active Publication Date: 2015-07-22
TIANJIN CHASE SUN PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the amplification reaction, it will be a great challenge to avoid this side reaction

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  • Preparation method of sulfonyl azide compounds
  • Preparation method of sulfonyl azide compounds
  • Preparation method of sulfonyl azide compounds

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Embodiment 1

[0041] Embodiment 1: a kind of preparation method of formula (I-A) imidazole-1-sulfonyl azide, comprises the steps:

[0042]

[0043] a. Dissolve N,N'-sulfonyldiimidazole (compound of formula (II-A); 100g, 0.50mol) in dichloromethane (1L), and add methyl trifluoromethanesulfonate dropwise at 0°C (50.9mL, 0.45mol), and then continue to react at 0°C for 2 hours, and the resulting solid is filtered, washed with dichloromethane, and vacuum-dried to obtain 163g of white solid powder (analyzed by nuclear magnetic resonance, which is 3-(imidazole-1 -sulfonyl)-1-methyl-3H-imidazole-1-trifluoromethanesulfonate, compound III-A), (yield 100%);

[0044]

[0045] b. Dissolve the compound of formula (III-A) (163g, 0.45mol) in ethyl acetate / water (1:1, 1080mL), add sodium azide (58.5g, 0.9mol) at 0°C, and the reaction solution Stir at 0° C. for 1.5 hours. After the reaction is complete, imidazole-1-sulfonyl azide (compound I-A after nuclear magnetic resonance analysis) is obtained.

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Abstract

The invention relates to a preparation method of sulfonyl azide compounds, which comprises the following steps: (a) reacting compounds disclosed as Formula (II) with methyl trifluoromethanesulfonate to obtain compounds disclosed as Formula (III), wherein the compounds disclosed as Formula (II) are compounds disclosed as Formula (II-1) or Formula (II-2), and the compounds disclosed as Formula (III) are compounds disclosed as Formula (III-1) or Formula (III-2); and (b) reacting the compounds disclosed as Formula (III) obtained in the step (a) with sodium azide to obtain sulfonyl azide compounds disclosed as Formula (I), wherein the sulfonyl azide compounds disclosed as Formula (I) are compounds disclosed as Formula (I-1) or Formula (I-2). The whole technical process has the advantages of mild conditions, high yield and high repetitiveness, is simple to operate, is safe and controllable, and can easily implement industrial production.

Description

technical field [0001] The invention relates to a preparation method of sulfonyl azide compounds. Background technique [0002] The scientific community has witnessed a flourishing era of azide-alkyne dipolar cycloaddition reactions. In traditional organic synthesis, organic azides are almost regarded as the only precursors of organic amines, and in the recently published articles on click chemistry, it has become an important intermediate. As a result, there has been a renewed focus on methods for the synthesis of organic azides and efforts to improve diazo transfer reactions from amines to organic azides with corresponding stereochemistry. [0003] The early diazo group transfer reaction began in 1967 (J.Am.Chem.Soc.1967,89,2633-2637; Tetrahedron, 1969,25,855-9), in sulfonyl azide (R-SO 2 -N 3 ), a group of primary amine anions were converted to azides in poor yields. Since then, sulfonyl azides have become the most studied and applied diazo transfer reagents. In 1972...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/56C07D231/12C07H5/04C07H1/00
Inventor 王鹏叶辉孙长海刘永辉袁海新郭伟康周立飞曹雪峰
Owner TIANJIN CHASE SUN PHARM CO LTD