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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1525549Generated: October 30, 2026

Methylamine → 3-Desbromo-3-chloro-Chlorantraniliprole

https://huagongshe.com/reaction/1525549

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 numberUS09084422B2
Source datasetuspto-grants-2015_07
ORD IDord-62e4a7ca0f09491a84431b6502d9580b
Source noteuspto-grants-2015_07