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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1386819Generated: November 2, 2026

Dimethylformamide → n-(3-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide

https://huagongshe.com/reaction/1386819

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPotassium CarbonateHCID 11430—
Reactant5-(Bromomethyl)-2-chlorothiazoleHCID 10130560—
Reactant3,6-Dihydro-3-methyl-N-nitro-2H-1,3,5-oxadiazin-4-amineHCID 136277959—
SolventWaterHCID 962—
SolventDichloromethaneHCID 6344—
Productn-(3-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramideHCID 107646—

Reaction Conditions

Temperature50 °C

Reaction Steps

3.18 g of 5-bromomethyl-2-chloro-thiazole, 12 ml of dimethylformamide, 1.99 g of 3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine and 3.79 g of potassium carbonate are combined and the mixture is stirred for 5 hours at 50° C. The mixture is cooled to room temperature and 50 ml of water and 50 ml of dichloromethane are added. The organic phase is separated off and dried over magnesium sulfate; the solvent is evaporated off in vacuo. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (1:1), yielding the title compound (compound 2-2).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06265585B1
Source datasetuspto-grants-2001_07
ORD IDord-cdcf23eee36945e8a9551518b50797b9
Source noteuspto-grants-2001_07