Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1873749Generated: October 30, 2026

Chloroform → 4-Methyl-2H-1,3-oxazine-2,6(3H)-dione

https://huagongshe.com/reaction/1873749

Reaction equation

Participants

RoleNameHCIDCharge
ReactantChloroformHCID 6212—
ReactantCitraconic AnhydridesHCID 12012—
ReactantAzidotrimethylsilaneHCID 78378—
SolventEthanolHCID 702—
Product4-Methyl-2H-1,3-oxazine-2,6(3H)-dioneHCID 535707—

Reaction Conditions

Temperature55 °C

Reaction Steps

At room temperature, 50.0 g of trimethylsilylazide was added to a mixture of 44.8 g of citraconic anhydride and 60 ml of chloroform. The mixture was stirred at 50-60° C. for 5 hours. After cooling the reaction mixture with an ice, 25.0 g of ethanol was added, followed by stirring for additional 30 minutes. The resulting solid was collected by filtration, and washed with a mixed solvent of chloroform and ethanol to obtain crude 4-methyl-2H-1,3-oxazine-2,6(3H)-dione represented by the formula:

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08304437B2
Source datasetuspto-grants-2012_11
ORD IDord-99eb1b6066ab4361925c5c054786214a
Source noteuspto-grants-2012_11