Sodium hydride → HCID 1280267, compound

HRID 2375912Notes

Reaction equation

HRID 2375912 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[NH:3][CH:2]=1.[H-].[Na+].[N+:14]([C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][CH:26]=1)[C:20](=[O:23])[CH2:21]Br)([O-:16])=[O:15]>CN(C=O)C>[N+:14]([C:17]1[CH:18]=[C:19]([C:20](=[O:23])[CH2:21][N:3]2[C:4](=[O:11])[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=[CH:2]2)[CH:24]=[CH:25][CH:26]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 1354087534(1H)-Quinazolinone

Product 1

HCID 1280267HCID 1280267, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4(3H)-quinazolinone (2.19 g, 15.0 mol) in anhydrous DMF (10 mL) was added NaH (60% dispersion in mineral oil, 0.719 g, 18.0 mmol) in two portions with caution. The mixture was stirred at rt for 30 min. 3-Nitrophenacyl bromide (4.39 g, 18.0 mmol) was added and the resulting suspension was stirred at rt for 16 h. Solvent was removed under reduced pressure. To the residue were added water (10 mL) and 4 N HCl (aq) to adjust the pH to ≈6. The solid material was collected by filtration, washed with water (20 mL) and dichloromethane (3×20 mL) to afford the title compound as a white powder. 1H-NMR (CD3OD, 400 MHz): δ=5.70 (d, J=10.0 Hz, 2H), 7.60 (d, J=7.2 Hz, 1H), 7.76 (d, J=8.4 Hz, 1H), 7.86-7.91 (m, 2H), 8.25 (d, J=8.0 Hz, 1H), 8.30 (s, 1H), 8.51-8.58 (m, 2H), 8.90 (t, J=1.2 Hz, 1H). MS (ES+): m/z 310.06 [MH+]. HPLC: tR=2.90 min (ZQ2000, polar—5 min).

Workup

  1. stirringthe resulting suspension was stirred at rt for 16 h
  2. customSolvent was removed under reduced pressure
  3. additionTo the residue were added water (10 mL) and 4 N HCl (aq)
  4. filtrationThe solid material was collected by filtration
  5. washwashed with water (20 mL) and dichloromethane (3×20 mL)

Sources & evidence

ORD record
ord-956aa8d96b1146c3a5ae3ae98acd3bf3
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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