US 12,234,217 B2
Method for preparing N-phenylpyrazole-1-carboxamides
Steven T. Booth, Wilmington, DE (US)
Assigned to FMC CORPORATION, Philadelphia, PA (US); and FMC AGRO SINGAPORE PTE. LTD., Singapore (SG)
Appl. No. 17/299,391
Filed by FMC CORPORATION, Philadelphia, PA (US); and FMC AGRO SINGAPORE PTE. LTD., Singapore (SG)
PCT Filed Nov. 22, 2019, PCT No. PCT/US2019/062778
§ 371(c)(1), (2) Date Jun. 3, 2021,
PCT Pub. No. WO2020/117493, PCT Pub. Date Jun. 11, 2020.
Claims priority of provisional application 62/774,436, filed on Dec. 3, 2018.
Prior Publication US 2022/0056007 A1, Feb. 24, 2022
Int. Cl. C07D 401/04 (2006.01)
CPC C07D 401/04 (2013.01) 19 Claims
 
1. A method for preparing a compound of Formula 1

OG Complex Work Unit Chemistry
wherein
X is O;
Z is N;
R1 is H, CH3, Cl or Br;
R2 is H, Br, Cl or CN;
R3 is H, C1-C4 alkyl or C4-C10 cycloalkylalkyl;
R4 is Cl, or Br; or
C1-C4 alkyl substituted with Q;
R5 is F, Cl or Br;
R6 is H, F or Cl;
Q is a 5- or 6-membered aromatic heterocyclic ring optionally substituted with one or more substituents independently selected from the group consisting of halogen, C1-C6 alkyl, C3-C6 cycloalkyl and C1-C6 haloalkyl;
comprising:
combining (1) a carboxylic acid compound of Formula 2,

OG Complex Work Unit Chemistry
wherein Z, R4, R5, R6, R7, and Q are as defined for the compound of Formula 1; and
(2) an aniline compound of Formula 3,

OG Complex Work Unit Chemistry
wherein X, R1, R2 and R3 are as defined for the compound of Formula 1;
(3) a sulfonyl chloride to form the compound of Formula 1; wherein the method comprises a continuous process comprising combining the compound of Formula 2, the compound of Formula 3, the sulfonyl chloride continuously in a reaction zone; and removing the compound of Formula 1 continuously in an isolation step further wherein the reaction zone comprises one or more continuous reaction vessels; and
(4) optionally in the presence of a base or solvent.