N-[4-(benzofuran-5-yl)thiazole-2-yl] amide as well as preparation method and application for same

A technology of benzofuran and thiazole, applied in the field of N-[4-(benzofuran-5-yl)thiazol-2-yl]amide and its preparation and application, can solve the problem of no herbicidal activity

Inactive Publication Date: 2013-10-09
HUNAN UNIV
View PDF5 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Indoor herbicidal activity screening found that such compounds have no obvious herbicidal activity

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • N-[4-(benzofuran-5-yl)thiazole-2-yl] amide as well as preparation method and application for same
  • N-[4-(benzofuran-5-yl)thiazole-2-yl] amide as well as preparation method and application for same
  • N-[4-(benzofuran-5-yl)thiazole-2-yl] amide as well as preparation method and application for same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Preparation of N-[4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)thiazol-2-yl]acetamide

[0040]

[0041] 0.41g (1.5 mmol) 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-aminothiazole, 0.45 mL acetic anhydride, room temperature Stir and react for 1.5 h. The reaction solution was poured into ice water, stirred, and a white solid was precipitated, filtered, neutralized with ammonia water, filtered, and dried to obtain N-[4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzene and furan-5-yl)thiazol-2-yl]acetamide, yield 76.6%, m.p. 252~254℃. 1 H NMR (CDCl 3 , 400M Hz) δ: 1.53(s, 6H, 2×CH 3 ), 2.00 (s, 3H, CH 3 ), 3.06 (s, 2H, CH 2 ), 3.90 (s, 3H, OCH 3 ), 6.96(s, 1H, thiazole-H), 7.21(s, 1H, C 6 h 2 ), 7.24(s, 1H, C 6 h 2 ), 10.51 (br, 1H, NH); D 2 After O exchange, the NH peak disappears.

Embodiment 2

[0043] Preparation of N-[4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)thiazol-2-yl]propionamide

[0044]

[0045] 0.41g (1.5 mmol) 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-aminothiazole, 0.45 mL propionic anhydride, room temperature Stir, react for 1.5 h, pour the reaction solution into ice water, stir, and precipitate a white solid, filter, neutralize with ammonia water, filter, and dry to obtain N-[4-(7-methoxy-2,2-dimethyl-2 ,3-Dihydrobenzofuran-5-yl)thiazol-2-yl]propionamide, yield 73.5%, m.p. 245~248℃. 1 H NMR (CDCl 3 , 400M Hz) δ: 1.15(t, J = 7.6 Hz, 3H, CH 3 ), 1.54(s, 6H, 2×CH 3 ), 2.29 (q, J = 7.6 Hz, 2H, CH 2 ), 3.07 (s, 2H, CH 2 ), 3.92 (s, 3H, OCH 3 ), 6.97(s, 1H, thiazole-H), 7.22(s, 1H, C 6 h 2 ), 7.24(s, 1H, C 6 h 2 ), 10.07 (br, H, NH).

Embodiment 3

[0047] Preparation of N-[4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)thiazol-2-yl]chloroacetamide

[0048]

[0049] 0.40 g (1.45 mmol) 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-2-aminothiazole, 4 drops of pyridine, 15 mL of tetrahydrofuran, Add 0.18 g (1.60 mmol) of chloroacetyl chloride dropwise and react for 20 min. Add ethyl acetate to precipitate a solid, and the filtrate is rotary evaporated and then column chromatographed to obtain N-[4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl) Thiazol-2-yl]chloroacetamide. Yield 80.3%, m.p. 215~217℃. 1 H NMR (CDCl 3 , 400M Hz) δ: 1.54(s, 6H, 2×CH 3 ), 3.07 (s, 2H, CH 2 ), 3.95(s, 3H, OCH 3 ), 4.27 (s, 2H, CH 2 Cl), 7.02(s, 1H, thiazole-H), 7.25(s, 1H, C 6 h 2 ), 7.26(s, 1H, C 6 h 2 ), 9.85 (br, 1H, NH).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention relates to N-[4-(benzofuran-5-yl)thiazole-2-yl] amide shown in a chemical structural formula I and the salts thereof, wherein Y, R1, R and R2 are selected from hydrogen, C1-C2 alkyl, C3-C4 linear alkyl or branched alkyl and the like; and N-[4-(benzofuran-5-yl)thiazole-2-yl] amide is prepared from 4-(2,3-dihydrobenzofuran-5-yl)-2-aminothiazole via acylation. N-[4-(benzofuran-5-yl)thiazole-2-yl] amide is good in bactericidal activity, and capable of being applied in preparation for a bactericide.

Description

technical field [0001] The present invention relates to novel compounds and applications thereof, in particular to the preparation of N-[4-(benzofuran-5-yl)thiazol-2-yl]amide and its application in the preparation of fungicides. Background technique [0002] Furanol (chemical name 2,2-dimethyl-2,3-dihydrobenzofuranphenol) is an important intermediate in the production of large-tonnage carbamate pesticides such as carbofuran, haoanwei and carbofuran. Carbamate pesticides have high activity and are widely used, but they are more toxic. Therefore, it is necessary to develop alternative products with lower toxicity and better activity to meet the market demand. As we all know, it takes 8-10 years to develop a new pesticide variety. In addition, there are many data and projects required for the registration of new pesticide varieties, and the cost is hundreds of millions of dollars. Therefore, the world's new pesticide creation companies shift part of their energy to use There a...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/04A01N43/78A01P3/00
Inventor 胡艾希李全付二霞伍智林欧晓明
Owner HUNAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap