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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1368019Generated: October 27, 2026

Phenacyl bromide → 3-(8-chloro-6-fluoro-3-phenyl-2H-1,4-benzoxazin-5-yl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidindione

https://huagongshe.com/reaction/1368019

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhenacyl bromideHCID 6259—
ReactantPotassium CarbonateHCID 11430—
Reactant1-methyl-6-trifluoromethyl-3-(6-amino4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneHCID 12056912—
SolventAcetoneHCID 180—
Product3-(8-chloro-6-fluoro-3-phenyl-2H-1,4-benzoxazin-5-yl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidindioneHCID 1205691118.7%

Reaction Steps

A mixture of 3-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.5 g), phenacyl bromide (0.29 g) and potassium carbonate (0.2 g) in acetone (30 ml) was stirred under reflux conditions for 1 hour. Then insoluble salt was removed through Celite and the filtrate concentrated under reduced pressure. The oily substance was purified by column chromatography on silica gel using ethyl acetate-hexane(1:4) as eluent to give the title compound (0.12 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06573218B1
Source datasetuspto-grants-2003_06
ORD IDord-4b90007f77b04608a4a49043146466ae
Source noteuspto-grants-2003_06