Sodium hydride → 1-(4-Bromo-phenyl)-3-[3-(3-isopropoxy-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-urea

HRID 362603Notes

Reaction equation

HRID 362603 reaction equation
[NH2:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH:19]([CH3:21])[CH3:20])[CH:13]=2)[C:10](=[O:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].[Br:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1>CN(C=O)C>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH:1][C:2]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH:19]([CH3:20])[CH3:21])[CH:13]=3)[C:10](=[O:22])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[O:34])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 756094-Bromophenyl isocyanateHCID 108277054(3H)-Quinazolinone, 2-amino-3-[3-(1-methylethoxy)phenyl]-

Product 1

HCID 105771091-(4-Bromo-phenyl)-3-[3-(3-isopropoxy-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-ureaYield 14.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-3-(3-isopropoxy-phenyl)-3H-quinazolin-4-one (295 mg, 1.0 mmol) in anhydrous DMF (10 mL) was added 50% NaH (48 mg, 1 mmol) at room temperature and stirred for 30 minutes. To this mixture was added, 4-bromo phenyl isocyanate and stirred for 2 hours at room temperature. The reaction mixture was quenched with water and concentrated. It was then diluted with ethyl acetate and filtered. The filtrate was concentrated and chromatographed using 100% CH3Cl to isolate pure product as a white solid (70 mg, 14.2%), mp 230°-233° C.

Workup

  1. additionTo this mixture was added
  2. customThe reaction mixture was quenched with water
  3. concentrationconcentrated
  4. additionIt was then diluted with ethyl acetate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-2a2f0da33a084ee49897eb00ca294c05
Source dataset
uspto-grants-1999_02
Patent number
US05869665

Reaction notes

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