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2-thiazolylacrylonitrile compounds and its synthetic method and application

A technology of thiazolyl acrylonitrile and its synthesis method, which is applied in the fields of botany equipment and methods, applications, organic chemistry, etc., and can solve the problem of the limited application of 2-thiazolyl acrylonitrile compounds

Inactive Publication Date: 2008-07-09
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Thiazole compounds play a very important role in pesticides, but 2-thiazolyl acrylonitrile compounds are rarely used in pesticides

Method used

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  • 2-thiazolylacrylonitrile compounds and its synthetic method and application
  • 2-thiazolylacrylonitrile compounds and its synthetic method and application
  • 2-thiazolylacrylonitrile compounds and its synthetic method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 4.72g (20mmol) 2-cyanomethyl-4-(2,6-difluorophenyl) thiazole and 3.05g (30mmol) triethylamine to 20mL tetrahydrofuran, add dropwise 2.76g (24mmol) chloroacetyl chloride , 40min dripping, then reacted at 66°C for 12h, after the reaction was completed, filtered, and the filter cake was recrystallized with chloroform to obtain light green crystal 2-[4-(2,6-difluorophenyl)-2-thiazolyl]- 4.40g of 3-hydroxy-3-chloromethylacrylonitrile, melting point 193-195°C, yield 70%.

[0027] of the compound 1 H NMR and IR are as follows,

[0028] 1 HNMR (CDCl 3 )δ=4.43(H, s, CH 2 Cl), 7.09~7.13 (2H, m, Ar- CH -CH- CH ), 7.40 (H, s, Triazole), 7.42~7.50 (H, m, Ar-CH- CH -CH), 14.67 (H, OH) IR (KBr, cm -1 )3378, 3155, 2201, 1524, 1610~1450, 1233, 783, 727

Embodiment 2

[0030] 4.72g (20mmol) of 2-cyanomethyl-4-(2,6-difluorophenyl)thiazole and 1.13g (28 mmol) of sodium hydroxide were added to 25mL of 1,4-dioxane, and 2.10g of (26mmol) acetyl chloride, after 40 minutes of dripping, then reacted at 100°C for 6 hours, after the reaction was completed, filtered, and the filter cake was recrystallized with chloroform to obtain white flaky crystals 2-[4-(2,6-difluorophenyl)- 4.36 g of 2-thiazolyl]-3-hydroxy-3-methacrylonitrile, melting point 197-198°C, yield 78%.

[0031] of the compound 1 H NMR and IR are as follows,

[0032] 1 HNMR (CDCl 3 )δ=2.41(3H, s, CH 3 ), 7.05~7.09 (2H, m, Ar- CH -CH- CH ), 7.36~7.46 (2H, m, Ar-CH- CH -CH&Triazole) IR (KBr, cm -1 )3453, 3179, 2191, 1513, 1610~1450, 1378, 1246, 790, 712

Embodiment 3

[0034] Add 4.72g (20mmol) 2-cyanomethyl-4-(2,6-difluorophenyl) thiazole and 3.22g (30mmol) sodium carbonate to 20mL dichloromethane, add 2.27g (24 mmol) propane dropwise Acyl chloride, after 40 minutes of dripping, then reacted at 40°C for 12 hours, after the reaction was completed, filtered, and the filter cake was recrystallized with chloroform to obtain a light green solid 2-[4-(2,6-difluorophenyl)-2-thiazolyl] - 4.21 g of 3-hydroxy-3-ethylacrylonitrile, melting point 172-174°C, yield 72%. of the compound 1 H NMR and IR are as follows,

[0035] 1 HNMR (CDCl 3 ) δ = 1.25 ~ 1.28 (3H, t, CH 3 ), 2.70~2.75 (2H, m, CH 2 ), 7.05~7.09 (2H, t, Ar- CH -CH- CH ), 7.37~7.41 (2H, m, Ar-CH- CH -CH&Triazole), 14.67 (H, OH) IR (KBr, cm -1 )3450, 3161, 2194, 1513, 1620~1480, 1459, 1237, 997

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Abstract

The invention discloses a 2-thiazolyl acrylonitriles coumpound, a synthesis process and an application. The structure of 2-thiazolyl acrylonitriles is showed as formula (I), wherein R is C1-C10 alkyl, C1-C5 halogenated alkyl, C3-C6 cycloalkyl, phenyl, benzyl or p-nitro phenyl. The synthesis process of the invention comprises conducting nucleophilic substitution towards2- cyanide-4-(2, 6-difluorophenyl) thiazole showed as formula (II) and acyl chloride showed in formula (III) in protonic solvent or nonprotonic solvent for 1-20h with 0-100 DEG C under the effect of acid binding agent to obtain reaction solution, and treating reaction solution to obtain 2-thiazolyl acrylonitriles compound. The 2-thiazolyl acrylonitriles compound can be used as herbicide, pesticide and pesticide, and adds new matters for the screening of herbicide, pesticide and pesticide.

Description

technical field [0001] The invention relates to a 2-thiazolyl acrylonitrile compound and its synthesis method and application. Background technique [0002] Thiazole compounds play a very important role in pesticides, but 2-thiazolylacrylonitrile compounds are rarely used in pesticides. Due to the high efficiency, low toxicity and structural diversity shown by 2-thiazolyl acrylonitrile compounds, they have very broad research and development prospects. In the present invention, a series of 2-thiazolyl acrylonitrile compounds are obtained by substituting the 3-position hydrogen with alkane and an aromatic ring. Contents of the invention [0003] The technical problem to be solved by the present invention is to provide a biologically active 2-thiazolylacrylonitrile compound, its synthesis method and its application. [0004] The structure of the 2-thiazolyl acrylonitrile compound of the present invention is shown in formula (I) [0005] [0006] where R is C 1 ~C 10 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/30A01N43/78A01P13/00A01P7/00A01P3/00
Inventor 沈德隆杨鹏谭成侠翁建全曹耀艳刘会君
Owner ZHEJIANG UNIV OF TECH
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