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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2169843Generated: November 1, 2026

Diethyl Ether → 5-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

https://huagongshe.com/reaction/2169843

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
ReactantDiphosgeneHCID 10426—
Reactant6-Methylanthranilic acidHCID 151210—
Solvent1,4-DioxaneHCID 31275—
Product5-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneHCID 1048752256%

Reaction Steps

Trichloromethyl carbonochloridate (2.04 mL, 16.9 mmol) was added to 2-amino-6-methylbenzoic acid (2.13 g, 14.1 mmol) in anhydrous dioxane (32 mL) under nitrogen, then refluxed for 30 minutes. Diethyl ether (100 mL) was added, and the precipitated solid was collected by filtration to give 5-methyl-1H-benzo[d][1,3]oxazine-2,4-dione (1.4 g, 56%) which was used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09049878B2
Source datasetuspto-grants-2015_06
ORD IDord-82ba5f6219bd4142ad6feb89bf1b6ff5
Source noteuspto-grants-2015_06