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

HRID 34546Notes

Reaction equation

HRID 34546 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[NH:8][C:7](=[O:13])[N:6]([CH3:14])[C:5]2(O)[C:15]([NH:17][C:18]([NH2:20])=S)=[O:16].[H-].[Na+].C(Br)C.CN(C)C=[O:30]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]3([C:15](=[O:16])[NH:17][C:18](=[O:30])[NH:20]3)[N:6]([CH3:14])[C:7](=[O:13])[NH:8][C:9]2=[CH:10][C:11]=1[Cl:12]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 142299966,7-Dichloro-3-methyl-4-hydroxy-4-thioureidocarbonyl-2-oxo-1,2,3,4-tetrahydroquinazoline

Product 1

HCID 142299976,7-Dichloro-3-methyl-spiro[1,2,3,4-tetrahydroquinazoline-4,4'-imidazolidine]-2,2',5'-trione

Procedure

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).

Workup

  1. stirringthe mixture is further stirred for 30 minutes
  2. distillationthe solvent is distilled off under reduced pressure
  3. additionTo 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)
  4. stirringthe mixture is stirred at 70° C. for 4 hours
  5. temperatureAfter cooling
  6. filtrationthe precipitates are taken by filtration
  7. washwashed with 10% aqueous sodium hydrogen carbonate solution
  8. customrecrystallized from dimethylformamide-water

Sources & evidence

ORD record
ord-642ffd02177e4409b8c254116aff5053
Source dataset
uspto-grants-1988_08
Patent number
US04762839

Reaction notes

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