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US 11,542,241 B2Granted
Efficient new process for synthesis of 2-amino-5-chloro-N,3-dimethylbenzamide
AssigneesFMC Corporation, FMC Argo Singapore Pte. Ltd.
InventorsLiang Chen, Yefeng Fan, Jianhua Mao, Zhijian Xu
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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.
Claims11
A method of preparing a compound of Formula VI, wherein
- each of R7-R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl, and C1-C5 alkyl;
- wherein at least one of R7-R10 is a halogen;
- and
- wherein R11 is selected from branched C1-C10 alkyl and unbranched C1-C10 alkyl, the method comprising
- I) forming a mixture comprising
- A) a compound of Formula V, wherein
- each of R7-R10 is independently selected from hydrogen, halogen, halogenated C1-C5 alkyl, and C1-C5 alkyl;
- wherein at least one of R7-R10 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 R1-R4 is independently selected from hydrogen, halogen, and C1-C5 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.
23 more elements
Dependencies are inferred from the claim text.