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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 61942Generated: October 31, 2026

Methylamine → 3-Desbromo-3-chloro-Chlorantraniliprole

https://huagongshe.com/reaction/61942

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethylamineHCID 6329—
Reactant6-chloro-2-[3-chloro-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-oneHCID 21113390—
SolventTetrahydrofuranHCID 8028—
Product3-Desbromo-3-chloro-ChlorantraniliproleHCID 11647840—

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of 6-chloro-2-[3-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrazol-5-yl]-8-methyl-4H-3,1-benzoxazin-4-one (i.e. the benzoxazinone product of Example 3, Step E) (6.32 g, 15.47 mmol) in tetrahydrofuran (50 mL) was added methylamine (2.0 M solution in THF, 38 mL, 77.38 mmol), and the reaction mixture was heated to 60° C., stirred for 1 hour and then cooled to room temperature. The tetrahydrofuran solvent was evaporated under reduced pressure, and the residual solid was purified by chromatography on silica gel to afford the title compound, a compound of the present invention, as a white solid (4.57 g) melting at 225-226° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09445593B1
Source datasetuspto-grants-2016_09
ORD IDord-cb75ce196bfb462a8e3e431f824fc2db
Source noteuspto-grants-2016_09