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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 61947Generated: October 25, 2026

Methylamine → Chlorantraniliprole

https://huagongshe.com/reaction/61947

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethylamineHCID 6329—
Reactant2-(3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl)-6-chloro-8-methyl-4H-benzo[d][1,3]oxazin-4-oneHCID 10253307—
SolventTetrahydrofuranHCID 8028—
ProductChlorantraniliproleHCID 11271640—

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of 2-[3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-6-chloro-8-methyl-4H-3,1-benzoxazin-4-one (i.e. the benzoxazinone product of Example 5, Step E) (0.20 g, 0.44 mmol) in tetrahydrofuran was added methylamine (2.0 M solution in THF, 0.514 mL, 1.02 mmol), and the reaction mixture was heated to 60° C. for 90 minutes and then cooled to room temperature. The tetrahydrofuran solvent was evaporated under reduced pressure, and the residual solid was triturated with ether, filtered, and dried to afford the title compound, a compound of the present invention, as a solid (40 mg), m.p. 162-164° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09445593B1
Source datasetuspto-grants-2016_09
ORD IDord-2e9e670fe83f48e28754e52734b7a773
Source noteuspto-grants-2016_09