Title of Invention

"PROCESS FOR PREPARING ACETAMIPRID"

Abstract A process for preparing acetamiprid, comprising: - taking cyanomethyl acetamidate in an organic solvent, - adding stoichiometric amount of cyanomethyl acetamidate to a mixture of a corresponding stoichiometric amount of 6-chloro-3-pyridalmethyl-N-memylamine and an organic solvent and refluxed at 30-35°C so as to obtain the product.
Full Text Field of Invention:
This invention relates to an improved method of preparation of Acetamiprid in presence of alkali in an organic solvent.
Background of Invention:
Acetamiprid (E) - N1 - [(6 - chloro - 3 - pyridyl) methyl] - N2 - cyano - N1 -methylacetamidine is known as an insecticide and is a pyridyhriemylamine insecticide.
US 5304566 talks about the pyridine compounds having useful insecticidal utility. This patent also discloses acetamiprid.
CN1413463A teaches the method of preparing acetamiprid comprises reacting N-cyano-N-methylacetamidine, anhydrous potassium carbonate, ammonium benzyltriethylchloride and dimethyl formamide.
Most of the known methods for the process of synthesis of acetamiprid involve two or more reaction steps and the yield is low.
Thus the object of the present invention is to provide a process for preparing acetamiprid that is capable of overcoming the aforesaid drawbacks and that significantly improves the yield of the aforesaid reaction.
Summary of the Invention:
The present invention relates to a process for preparing acetamiprid comprising:
- adding cyanomethyl acetamidate in an organic solvent,
- adding stoichiometric amount of cyanomethyl acetamidate to a mixture of a corresponding stoichiometric amount of 6-chloro-3-pyridalmethyl-N-methylamine and an organic solvent and refluxed at 30-35°C so as to obtain the product.
The organic solvent used for carrying out the reaction is dichloroethane.

The cyanomethyl acetamidate is continuously added drop wise into a mixture of the 6-chloro-3-pyridalmethyl-N-methylamine and an organic solvent wherein, rate of addition of cyanomethyl acetamidate into the mixture of 6-chloro-3-pyridalmemyl-N-methylamine and an organic solvent is 7.0 gm/hour.
Detailed Description of the Invention:
Preparation of acetamiprid according to the process of this invention is described in detail as follows.
The process of manufacturing involves condensation reaction of cyano methyl acetamidate (AC-B) with 6-chloro-3-pyridyl methyl-N-methyl amine (AC-A) in presence of organic solvent.
Cyanomethyl acetamidate is taken in an organic solvent, stoichiometric amount of cyanomethyl acetamidate is continuously added drop wise at the rate of 7.0 gm/hour to a mixture of a corresponding stoichiometric amount of 6-chloro-3-pyridalmemyl-N-memylamine and an organic solvent and refluxed at 30-35°C so as to obtain the product.
For every mole of AC-B, 1.05 mole of AC-A is used.
More preferably cyanomethyl acetamidate is taken in dichloroethane, stoichiometric amount of cyanomethyl acetamidate is added to a mixture of a corresponding stoichiometric amount of 6-chloro-3-pyridalmethyl-N-methylamine and dichloroethane and refluxed at 30-35°C so as to obtain the product.
The crude acetamiprid can be purified by various chromatography techniques, more preferably by HPLC.
The yield of the reaction is about 92-94% , which is quite high in comparison to the previously known methods.
The present invention will now be explained with examples however; the scope of the invention should not be limited to it.
Example 1:
6-chloro-3-pyridyl methyl-N-methyl amine (15.7 gm) is taken in 8ml of dichloroethane at 30-35°C. The reaction mass is continuously stirred. A solution of cyanomethyl acetamidate (10.3 gm) in 8 ml dichloroethane is added. The AC-B is added at the rate of 7.0gm/hr and the temperature of the reaction is maintained at 30-35°C. The mixture is continuously stirred for 2hrs. The reaction mass is checked for completion. When the reaction is complete, the mixture is cooled at 85°C. The material is filtered and washed with a little amount of dichloroethane. The product is dried at 40°C. Yield =21.1 gm (95.05%), purity=98.75%.



We Claims :-
1. A process for preparing acetamiprid, comprising:
- adding cyanomethyl acetamidate in an organic solvent,
- adding stoichiometric amount of cyanomethyl acetamidate to a mixture of a corresponding stoichiometric amount of 6-chloro-3-pyridamethyl-N-methylamine and an organic solvent and refluxed at 30-35°C so as to obtain the product.

2. The process as claimed in claim 1 wherein the said cyanomethyl acetamidate is continuously added drop wise into a mixture of the 6-chloro-3-pyridalmethyl-N-methylamine and an organic solvent wherein, rate of addition of cyanomethyl acetamidate into the mixture of 6-chloro-3-pyridalmethyl-N-methylamine and an organic solvent is 7.0 gm/hour.
3. The process as claimed in claim 1 wherein the organic solvent is dichloroethane.
4. A process for preparing acetamiprid substantially as herein described with reference to the foregoing examples.

Documents:

654-del-2005-Abstract-(13-12-2013).pdf

654-del-2005-abstract.pdf

654-del-2005-Claims-(13-12-2013).pdf

654-del-2005-claims.pdf

654-del-2005-Correspondence Others-(13-12-2013).pdf

654-del-2005-correspondence-others.pdf

654-del-2005-description (complete).pdf

654-del-2005-form-1.pdf

654-del-2005-form-2.pdf

654-del-2005-Form-3-(13-12-2013).pdf

654-del-2005-form-3.pdf

654-del-2005-Form-5-(13-12-2013).pdf

654-del-2005-gpa.pdf


Patent Number 259817
Indian Patent Application Number 654/DEL/2005
PG Journal Number 13/2014
Publication Date 28-Mar-2014
Grant Date 27-Mar-2014
Date of Filing 24-Mar-2005
Name of Patentee INSECTICIDES (INDIA) LIMITED
Applicant Address 401, 402 LUSA TOWER, COMMERCIAL COMPLEX, AZADPUR, DELHI-110 033, INDIA
Inventors:
# Inventor's Name Inventor's Address
1 KUMAR MUKESH R & D LAB, INSECTICIDES (INDIA) LIMITED, F443-444, RIICO INDUSTRIAL AREA, CHOPANKI (BIWADI), RAJASTHAN
2 SINGHAL B.S R & D LAB, INSECTICIDES (INDIA) LIMITED, F443-444, RIICO INDUSTRIAL AREA, CHOPANKI (BIWADI), RAJASTHAN
PCT International Classification Number A01N 47/10
PCT International Application Number N/A
PCT International Filing date
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 NA