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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 34546Generated: October 29, 2026

Dimethylformamide → 6,7-Dichloro-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione

https://huagongshe.com/reaction/34546

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantEthyl BromideHCID 6332—
ReactantSodium hydrideHCID 24758—
Reactant6,7-Dichloro-3-methyl-4-hydroxy-4-thioureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazolineHCID 14229996—
Product6,7-Dichloro-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trioneHCID 14229997—

Reaction Steps

6,7-Dichloro-3-methyl-4-hydroxy-4-thioureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline (2.8 g) is dissolved in dimethylformamide (30 ml), and thereto is added sodium hydride (60% oily suspension) (0.32 g), and the mixture is stirred at room temperature for 30 minutes. To the mixture is added ethyl bromide (2 ml), and the mixture is further stirred for 30 minutes, and then the solvent is distilled off under reduced pressure. To the residue [i.e. 6,7-dichloro-3-methyl-4-hydroxy-4-(2-methylisothioureido)-carbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline] is added 10% hydrochloric acid (30 ml), and the mixture is stirred at 70° C. for 4 hours. After cooling, the precipitates are taken by filtration, washed with 10% aqueous sodium hydrogen carbonate solution and then recrystallized from dimethylformamide-water to give 6,7-dichloro-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione (1.4 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04762839
Source datasetuspto-grants-1988_08
ORD IDord-642ffd02177e4409b8c254116aff5053
Source noteuspto-grants-1988_08