Efficient new process for synthesis of 2-amino-5-chloro-N,3-dimethylbenzamide

Patent metadata

Field	Value
Publication number	US-11542241-B2
Application number	US-202217721781-A
Country	US
Kind code	B2
Filing date	Apr 15, 2022
Priority date	Nov 1, 2019
Publication date	Jan 3, 2023
Grant date	Jan 3, 2023

Abstract

Described herein are novel methods of synthesizing 2-amino-5-chloro-N,3-dimethylbenzamide. Compounds prepared by the methods disclosed herein are useful for preparation of certain anthranilamide compounds that are of interest as insecticides, such as, for example, the insecticides chlorantraniliprole and cyantraniliprole.

First claim

What is claimed is:

1. A method of preparing a compound of Formula VI, wherein

each of R 7 -R 10 is independently selected from hydrogen, halogen, halogenated C 1 -C 5 alkyl, and C 1 -C 5 alkyl;
wherein at least one of R 7 -R 10 is a halogen; and
wherein R 11 is selected from branched C 1 -C 10 alkyl and unbranched C 1 -C 10 alkyl, the method comprising
I) forming a mixture comprising
A) a compound of Formula V, wherein

each of R 7 -R 10 is independently selected from hydrogen, halogen, halogenated C 1 -C 5 alkyl, and C 1 -C 5 alkyl;
wherein at least one of R 7 -R 10 is a halogen; and
wherein the compound of Formula V is prepared according to a method comprising
i) forming a first mixture comprising
 a) a compound of Formula III, wherein

 each of R 1 -R 4 is independently selected from hydrogen, halogen, and C 1 -C 5 alkyl;
 b) a solvent; and
 c) a halogenation reagent;
ii) reacting the first mixture;
iii) introducing a second mixture to the first mixture to form a third mixture, the second mixture comprising
 d) an oxidation agent; and
iv) reacting the third mixture, wherein the third mixture is reacted in the presence of a catalyst;

B) an alkylamine; and
C) a solvent; and

II) reacting the mixture.

2. The method of claim 1 , wherein the alkylamine comprises a functional group selected from branched C 1 -C 10 alkyl and unbranched C 1 -C 10 alkyl.

3. The method of claim 1 , wherein the solvent C) is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, methanol, ethanol, isopropanol, ethyl acetate, isopropyl acetate, and combinations thereof.

4. The method of claim 1 , wherein the method step II) of reacting the mixture occurs at a reaction temperature in the range of 0° C. to 100° C.

5. The method of claim 1 , wherein the solvent b) is selected from acetonitrile, dichloroethane, toluene, chlorobenzene, xylene, acetic acid, acetic anhydride, propionic acid, butyric acid, and combinations thereof.

6. The method of claim 1 , wherein the halogenation reagent is selected from a chlorination reagent, a bromination reagent, an iodination reagent, and combinations thereof.

7. The method of claim 1 , wherein the method step ii) of reacting the first mixture occurs at a reaction temperature in the range of 20° C. to 140° C.

8. The method of claim 1 , wherein the oxidation agent is selected from oxygen, chlorine, sodium hypochlorite, chromium trioxide, 3-chloroperoxybenzoic acid, hydrogen peroxide, peroxyacetic acid, potassium peroxymonosulfate, potassium permanganate, and combinations thereof.

9. The method of claim 1 , wherein the catalyst is selected from sulfuric acid, hydrogen chloride, nitric acid, and combinations thereof.

10. The method of claim 1 , wherein the method step iv) of reacting the third mixture occurs at a reaction temperature in the range of 20° C. to 100° C.

11. The method of claim 1 , wherein the compound of Formula III is prepared according to a method comprising
I) forming a mixture comprising
A) a compound of Formula II, wherein

each of R 1 -R 5 is independently selected from hydrogen, halogen, and C 1 -C 5 alkyl; and
wherein the compound of Formula II is prepared according to a method comprising
i) forming a mixture comprising
a) a compound of Formula I, wherein

each of R 1 -R 5 is independently selected from hydrogen, halogen, and C 1 -C 5 alkyl;
b) chloral hydrate;
c) a hydroxylamine derivative;
d) a solvent;
e) an inorganic salt; and
f) an acid; and

ii) reacting the mixture; and

B) an acid; and

II) reacting the mixture.

Assignees

• Fmc Corp
• Fmc Agro Singapore Pte Ltd
• Fmc Argo Singapore Pte Ltd

Inventors

• Chen Liang
• Fan Yefeng
• Mao Jianhua
• Xu Zhijian

Classifications

• C07D265/26 Primary

  Two oxygen atoms, e.g. isatoic anhydride · CPC title

• C07C231/10 Primary

  from compounds not provided for in groups C07C231/02 - C07C231/08 · CPC title

• C07C249/12

  by reactions not involving the formation of oxyimino groups · CPC title

• C07C237/30

  having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms · CPC title

• C07D209/38

  in positions 2 and 3, e.g. isatin · CPC title