US 12,304,893 B2
Process for synthesis of 2-amino-5-chloro-N-,3-dimethylbenzamide
Liang Chen, Shanghai (CN); Yefeng Fan, Shanghai (CN); Jianhua Mao, Shanghai (CN); and Zhijian Xu, Shanghai (CN)
Assigned to FMC CORPORATION, Philadelphia, PA (US); and FMC IP TECHNOLOGY GMBH, Neuhausen (CH)
Filed by FMC Corporation, Philadelphia, PA (US); and FMC Agro Singapore Pte. Ltd., Singapore (SG)
Filed on Nov. 29, 2022, as Appl. No. 18/070,827.
Application 18/070,827 is a division of application No. 17/721,781, filed on Apr. 15, 2022, granted, now 11,542,241.
Application 17/721,781 is a continuation of application No. PCT/US2020/057726, filed on Oct. 28, 2020.
Claims priority of provisional application 62/929,138, filed on Nov. 1, 2019.
Prior Publication US 2023/0096826 A1, Mar. 30, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07C 237/30 (2006.01); C07C 231/14 (2006.01); C07C 237/28 (2006.01); C07D 209/38 (2006.01); C07D 265/26 (2006.01)
CPC C07D 265/26 (2013.01) [C07C 231/14 (2013.01); C07C 237/28 (2013.01); C07D 209/38 (2013.01)] 17 Claims
 
1. A method of preparing a compound of Formula VI, wherein

OG Complex Work Unit Chemistry
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

OG Complex Work Unit Chemistry
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

OG Complex Work Unit Chemistry
 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) adding an oxidation agent to the reacted first mixture in the presence of a catalyst to form a further mixture; and
iv) reacting the third mixture;
B) an alkylamine; and
C) a solvent; and
II) reacting the mixture.