Title:
METHOD FOR PREPARING BENZOTHIAZOLE COMPOUND BY USING N-(2-BROMOPHENYL)THIOAMIDE UNDER PROMOTION OF VISIBLE LIGHT
Document Type and Number:
WIPO Patent Application WO/2022/178693
Kind Code:
A1
Abstract:
A method for preparing a benzothiazole compound by using N-(2-bromophenyl)thioamide under promotion of visible light, comprising: under the protection of inert gas, adding reactants, N-(2-bromophenyl)thioamide and an inorganic base, into a reaction vessel provided with a stirring device according to a molar ratio of 1:0.5, next, adding dimethyl sulfoxide, and then under visible light irradiation, stirring to react at room temperature for 2-24 hours to obtain a benzothiazole compound. In the present method, sodium phosphate is used as alkali to carry out a series of intramolecular cross-coupling reactions of N-(2-bromophenyl)thioamide under the irradiation of a 45W household compact fluorescent lamp, without adding any photosensitizer or transition metal catalyst, such that a high yield of the benzothiazole compound can be obtained, and the whole process is environmentally friendly, efficient, and easy to implement.
Inventors:
LI HONGXI (CN)
WANG HAO (CN)
LI HAIYAN (CN)
WANG HAO (CN)
LI HAIYAN (CN)
Application Number:
PCT/CN2021/077531
Publication Date:
September 01, 2022
Filing Date:
February 23, 2021
Export Citation:
Assignee:
UNIV SOOCHOW (CN)
International Classes:
C07D277/66; C07D417/04
Domestic Patent References:
| WO2015190718A1 | 2015-12-17 |
Foreign References:
| CN103788013A | 2014-05-14 | |||
| CN112979581A | 2021-06-18 |
Other References:
BOWMAN W.RUSSELL, HEANEY HARRY, SMITH PHILIP H.G.: "Intramolecular aromatic substitution (SRN1) reactions; use of entrainment for the preparation of benzothiazoles", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 23, no. 48, 1 January 1982 (1982-01-01), Amsterdam , NL , pages 5093 - 5096, XP055961522, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)85581-1
MUTHUSAMY SENGODEN, RANGASAMY PARAMASIVAM, VAYALAKKAVOOR T. RAMAKRISHNAN: "Photochemical Synthesis of 2-Substituted Benzothiazoles", J.HETEROCYCLIC CHEM., vol. 28, 31 May 1991 (1991-05-31), pages 759 - 763, XP055961547
XU ZE-MING, LI HONG-XI, YOUNG DAVID JAMES, ZHU DA-LIANG, LI HAI-YAN, LANG JIAN-PING: "Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C–H Thiolation via Reverse Hydrogen Atom Transfer", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 21, no. 1, 4 January 2019 (2019-01-04), US , pages 237 - 241, XP055961541, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.8b03679
MUTHUSAMY SENGODEN, RANGASAMY PARAMASIVAM, VAYALAKKAVOOR T. RAMAKRISHNAN: "Photochemical Synthesis of 2-Substituted Benzothiazoles", J.HETEROCYCLIC CHEM., vol. 28, 31 May 1991 (1991-05-31), pages 759 - 763, XP055961547
XU ZE-MING, LI HONG-XI, YOUNG DAVID JAMES, ZHU DA-LIANG, LI HAI-YAN, LANG JIAN-PING: "Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C–H Thiolation via Reverse Hydrogen Atom Transfer", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 21, no. 1, 4 January 2019 (2019-01-04), US , pages 237 - 241, XP055961541, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.8b03679
Attorney, Agent or Firm:
SUZHOU CREATOR PATENT AND TRADEMARK AGENCY, LTD (CN)
Download PDF: