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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 905892Generated: October 29, 2026

Phosgene → 5-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

https://huagongshe.com/reaction/905892

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhosgeneHCID 6371—
Reactant2-Amino-6-chlorobenzoic acidHCID 75071—
Solvent1,4-DioxaneHCID 31275—
Product5-chloro-2,4-dihydro-1H-3,1-benzoxazine-2,4-dioneHCID 639058—

Reaction Conditions

Temperature0 °C

Reaction Steps

In a 250 mL round-bottom flask under N2 was dissolved 2-amino-6-chlorobenzoic acid (11.69 g, 68 mmol) in 100 mL of 1,4-dioxane. The solution was cooled to 0° C. and to this solution was added phosgene (36 ml, 68 mmol) via a dropping funnel The reaction mixture was stirred for 24 hours allowing to warm to 23° C. (rt). The resulting white solid was filtered off and washed with 1,4-dioxane and Et2O. Yield=12.5 g, 93%

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08012968B2
Source datasetuspto-grants-2011_09
ORD IDord-ec25d042770c42778ae889a25601f639
Source noteuspto-grants-2011_09