Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method for novel insecticide indoxacarb

A technology of indoxacarb and insecticide, which is applied in the field of preparation of new insecticide indoxacarb, can solve problems such as danger, and achieve the effects of good purity, good product purity and high yield

Inactive Publication Date: 2014-12-10
CHANGZHOU UNIV
View PDF7 Cites 7 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The present invention adopts the production technology of green cleaning process, that is, protects with fluorenylmethoxycarbonyl chloride, deprotects in alkaline solution, and then reacts with methyl (chlorocarbonyl)[4-(trifluoromethoxy)phenyl]carbamate The method for preparing indoxacarb by condensation reaction solves the problems such as the danger of the hydrogenation reactant in the preparation of indoxacarb, and recycles and uses FMO. It is a safe and clean process production technology for the mass production of the new insecticide indoxacarb Provide technical support, its preparation process is as follows:

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
  • Preparation method for novel insecticide indoxacarb
  • Preparation method for novel insecticide indoxacarb

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0021] Example 1: Preparation of hydrazine carboxylate fluorene methyl ester

[0022] 80% hydrazine hydrate (24.5g, 0.40mol) was added to a 500mL reaction flask, and a solution of Fmoc-Cl (51.8g, 0.20mol) in tetrahydrofuran (280ml) was added dropwise at -20°C. After the dropwise addition was completed in about 2 hours , then continue to stir for 30min, stop the reaction, pour it into a separatory funnel, stand still, separate the upper organic layer, evaporate the solvent under reduced pressure, cool the residue, and filter to obtain the crude hydrazine carboxylic acid fluorene methyl ester, which is washed with ethyl acetate. After recrystallization, 32.7 g of hydrazine carboxylate fluorene methyl ester was obtained as white needle crystals. Yield: 85.7%, melting point: 168-170°C. 1 HNMR(DMSO)δ(ppm): 4.05(s, 2H), 4.16-4.31(m, 3H), 7.31(t, 2H, J=7.3Hz), 7.40(t, 2H, J=7.3Hz), 7.67 (d, 2H, J=7.3 Hz), 7.86 (d, 2H, J=7.3 Hz), 8.36 (s, 1H).

example 2

[0023] Example 2: Preparation of hydrazine carboxylate fluorene methyl ester

[0024]80% hydrazine hydrate (26.8g, 0.60mol) was added to a 500mL reaction flask, and a solution of Fmoc-Cl (51.8g, 0.20mol) in tetrahydrofuran (360ml) was added dropwise at -10°C, and the dropwise addition was completed within about 2 hours. , and then continue to stir for 60 min, stop the reaction, pour it into a separatory funnel, stand still, separate the upper organic layer, remove the solvent by distillation under reduced pressure, cool the residue, and filter to obtain the crude hydrazine carboxylate fluorene methyl ester, which is washed with ethyl acetate. After recrystallization, 33.2 g of hydrazine carboxylate fluorene methyl ester was obtained as white needle crystals. Yield: 87.0%.

example 3

[0025] Example 3: Preparation of (+)[5-chloro-2,3--hydrogen-2-hydroxy-2-methoxycarboxy-1H-indene-ylidene]hydrazine carboxylate fluorene methyl ester

[0026] Into a 500mL reaction flask, add (+) methyl 5-chloro-1,3-dihydro-2-hydroxy-1-oxo-2H-indene-2-carboxylate (24.1g, 0.10mol), hydrazine carboxylic acid Fluorene methyl ester (25.3 g, 0.10 mol), p-toluenesulfonic acid (3.0 g, 0.015 mol) and methanol (250 ml). Heated reflux reaction for 20h, after the reaction,

[0027] Cool and filter to obtain) [5-chloro-2,3--hydrogen-2-hydroxy-2-methoxycarboxy-1H-indene-idene] hydrazine carboxylic acid fluorene methyl ester crude product, recrystallize from methanol, filter , dried in vacuo to give a white solid [5-chloro-2,3--hydrogen-2-hydroxy-2-methoxycarboxy-1H-indene-idene]hydrazine carboxylate fluorene methyl ester 39.5g, yield For 82.8%, melting point: 172-174 ℃. 1 HNMR (CDCl 3 ), δ(ppm): 3.633(d, 1H, J=5.7Hz), 3.812(d, 1H, J=5.7Hz), 4.122(s, 3H), 4.532(m, 1H), 4.754(m, 2H) ), 7...

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 discloses a preparation method for a novel insecticide indoxacarb. The preparation method comprises the following steps: taking (+)5-chlorine-1,3-dihydro-2-hydroxyl-1-oxo-2H-indene-methyl carboxylate and 4-(trifluoromethoxy)benzenaime as raw materials, protecting (+)5-chlorine-1,3-dihydro-2-hydroxyl-1-oxo-2H-indene-methyl carboxylate by virtue of fluorenylmethyl chloroformate, and carrying out cyclization to prepare 2-( fluorenylmethyl)-7-chlorinindene-[1,2-e][1,34]] oxadiazine-2,4a(3H, 5H)-dicarboxylic acid-4a-methyl ether; reacting trifluoromethoxyaniline and methylchloroformate with phosgene to prepare (chlorocarbonyl)[4-(trifluoromethoxy)phenyl] methyl carbamate; carrying out deprotection on 2-( fluorenylmethyl)-7-chlorinindene-[1,2-e][1,34]] oxadiazine-2,4a(3H, 5H)-dicarboxylic acid-4a-methyl ether in alkaline solution and then carrying out condensation reaction with (chlorocarbonyl)[4-(trifluoromethoxy)phenyl] methyl carbamate to prepare the indoxacarb. The process yield of the indoxacarb is high and the purity of the indoxacarb is good.

Description

technical field [0001] The invention relates to a preparation method of a novel insecticide indoxacarb, in particular to a preparation method with (+)5-chloro-1,3-dihydro-2-hydroxy-1-oxo-2H-indene-2 -Methyl carboxylate (formula 2) and p-trifluoromethoxyaniline (formula 7) as raw materials, through fluorene methoxycarbonyl chloride (formula 3) protection, cyclization carbonylation and other reactions to prepare key two key intermediates 2 -(Fluorenylmethyl)-7-chloroindeno[1,2-e][1,3,4]]oxadiazine-2,4a(3H,5H)-dicarboxylic acid-4a-methyl ester ( formula 5) and methyl (chlorocarbonyl)[4-(trifluoromethoxy)phenyl]carbamate (formula 9), which are then combined with (chlorocarbonyl)[4-(trifluoromethoxy) through deprotection A method for preparing indoxacarb by condensation reaction of methyl phenyl]carbamate (Formula 9) belongs to the field of agricultural chemistry. Background technique [0002] According to the statistics of the World Food and Agriculture Organization, the loss ...

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
IPC IPC(8): C07D273/04
CPCC07D273/04
Inventor 徐德锋柳丽
Owner CHANGZHOU UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com