Title:
REACTION METHOD FOR SECONDARY AMINE AND O-DIIODOBENZENE
Document Type and Number:
WIPO Patent Application WO/2024/011414
Kind Code:
A1
Abstract:
Disclosed in the present invention is a reaction method for secondary amine and o-diiodobenzene, comprising: reacting secondary amine with o-diiodobenzene in the presence of an alkali metal hydride or a Grignard reagent to complete the reaction of secondary amine and o-diiodobenzene. Disclosed in the present invention is rapid preparations for arylamine compounds from o-diiodobenzene and secondary amine under the effect of sodium hydride, wherein the reactions are rapid, simple and gentle and are a novel method for rapidly achieving N-arylation. The main products of the reactions are 2-iodo-arylamine compounds, which are easy to convert and have greater value in use. The present invention especially solves the defects of long reaction time, high preparation cost, serious environmental pollution and the like since an N-arylation method in the prior art requires the conditions of high temperature, metal catalysis and the like.
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Inventors:
ZHANG SHILEI (CN)
ZHU WENJING (CN)
JIANG YUANRUI (CN)
HUANG JIAWEN (CN)
CHEN XIN (CN)
FANG CHUNHUI (CN)
HU YANWEI (CN)
ZHU WENJING (CN)
JIANG YUANRUI (CN)
HUANG JIAWEN (CN)
CHEN XIN (CN)
FANG CHUNHUI (CN)
HU YANWEI (CN)
Application Number:
PCT/CN2022/105227
Publication Date:
January 18, 2024
Filing Date:
July 12, 2022
Export Citation:
Assignee:
UNIV SOOCHOW (CN)
International Classes:
C07C211/52; C07C209/10; C07C211/56; C07C211/59; C07D209/08; C07D209/80; C07D209/86; C07D213/38; C07D213/68; C07D213/74; C07D217/04; C07D219/02; C07D223/22; C07D231/12; C07D231/56; C07D239/42; C07D257/04; C07D279/22; C07D295/073; C07D513/04
Foreign References:
| CN113735751A | 2021-12-03 | |||
| CN113735752A | 2021-12-03 | |||
| CN113735777A | 2021-12-03 | |||
| CN1518534A | 2004-08-04 |
Other References:
XUE, FEI: "The Research on Reactions of C-N Bond Formation", ENGINEERING SCIENCE & TECHNOLOGY I, CHINA MASTER’S THESES FULL-TEXT DATABASE, no. 11, 15 November 2008 (2008-11-15), pages 22 - 26, ISSN: 1674-0246
PAIN A.J.: "MECHANISMS AND MODELS FOR COPPER MEDIATED NUCLEOPHILIC AROMATIC SUBSTITUTION. 2. A SINGLE CATALYTIC SPECIES FROM THREE DIFFERENT OXIDATION STATES OF COPPER IN AN ULLMANN SYNTHESIS OF TRIARYLAMINES.", JOURNAL OF THE CHEMICAL SOCIETY, vol. 109, 1 January 1987 (1987-01-01), pages 1496 - 1502, XP000913833, ISSN: 0368-1769, DOI: 10.1021/ja00239a032
BARKER, TIMOTHY J. ET AL.: "Titanium-Mediated Amination of Grignard Reagents Using Primary and Secondary Amines", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 50, no. 36, 18 July 2011 (2011-07-18), pages 8325 - 8328, XP072086344, ISSN: 1433-7851, DOI: 10.1002/anie.201103700
FAN GUANG-GAO, JIANG BO-WEN, SANG WEI, CHENG HUA, ZHANG RUI, YU BAO-YI, YUAN YE, CHEN CHENG, VERPOORT FRANCIS: "Metal-Free Synthesis of Heteroaryl Amines or Their Hydrochlorides via an External-Base-Free and Solvent-Free C–N Coupling Protocol", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 86, no. 21, 5 November 2021 (2021-11-05), pages 14627 - 14639, XP093129219, ISSN: 0022-3263, DOI: 10.1021/acs.joc.1c01467
PAIN A.J.: "MECHANISMS AND MODELS FOR COPPER MEDIATED NUCLEOPHILIC AROMATIC SUBSTITUTION. 2. A SINGLE CATALYTIC SPECIES FROM THREE DIFFERENT OXIDATION STATES OF COPPER IN AN ULLMANN SYNTHESIS OF TRIARYLAMINES.", JOURNAL OF THE CHEMICAL SOCIETY, vol. 109, 1 January 1987 (1987-01-01), pages 1496 - 1502, XP000913833, ISSN: 0368-1769, DOI: 10.1021/ja00239a032
BARKER, TIMOTHY J. ET AL.: "Titanium-Mediated Amination of Grignard Reagents Using Primary and Secondary Amines", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 50, no. 36, 18 July 2011 (2011-07-18), pages 8325 - 8328, XP072086344, ISSN: 1433-7851, DOI: 10.1002/anie.201103700
FAN GUANG-GAO, JIANG BO-WEN, SANG WEI, CHENG HUA, ZHANG RUI, YU BAO-YI, YUAN YE, CHEN CHENG, VERPOORT FRANCIS: "Metal-Free Synthesis of Heteroaryl Amines or Their Hydrochlorides via an External-Base-Free and Solvent-Free C–N Coupling Protocol", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 86, no. 21, 5 November 2021 (2021-11-05), pages 14627 - 14639, XP093129219, ISSN: 0022-3263, DOI: 10.1021/acs.joc.1c01467
Attorney, Agent or Firm:
SUZHOU CREATOR PATENT AND TRADEMARK AGENCY, LTD (CN)
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