Diphosgene → 3-[1-(4-chloro-phenyl)-ethyl]-1H-quinazoline-2,4-dione

HRID 388484Notes

Reaction equation

HRID 388484 reaction equation
[NH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[CH3:8])=[O:5].Cl[C:21](OC(Cl)(Cl)Cl)=[O:22].[OH-].[Na+]>C1COCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH:7]([N:6]2[C:4](=[O:5])[C:3]3[C:2](=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:1][C:21]2=[O:22])[CH3:8])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 10426DiphosgeneHCID 14798Sodium HydroxideHCID 174435132-amino-N-[1-(4-chloro-phenyl)-ethyl]-benzamide

Product 1

HCID 687437773-[1-(4-chloro-phenyl)-ethyl]-1H-quinazoline-2,4-dioneYield 166.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-amino-N-[1-(4-chloro-phenyl)-ethyl]-benzamide (115 mg, 0.42 mmol) in THF (30 mL) is added trichloromethyl chloroformate (50 mg, 0.25 mmol). The mixture is stirred at 90° C. for 4 hours. The reaction mixture is allowed to cool to room temperature, neutralizes with 1M NaOH aq. The reaction mixture is extracted with EtOAc (50 mL×3). The organic layer is dried over sodium sulfate and is concentrated to give the desired 3-[1-(4-chloro-phenyl)-ethyl]-1H-quinazoline-2,4-dione (125 mg, 99%).

Workup

  1. temperatureto cool to room temperature
  2. extractionis extracted with EtOAc (50 mL×3)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationis concentrated

Sources & evidence

ORD record
ord-386acfff279e44338a8fec0676a6eb86
Source dataset
uspto-grants-2013_02
Patent number
US08377949B2

Reaction notes

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