Sodium Acetate → HCID 178441860, compound

HRID 2255091Notes

Reaction equation

HRID 2255091 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH2:13][CH2:14][CH2:15][CH3:16])=[N:7][C:6]2=[O:17].[C:18]([O-:21])(=[O:20])[CH3:19].[Na+]>CN(C=O)C>[C:18]([O:21][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([CH2:13][CH2:14][CH2:15][CH3:16])=[N:7][C:6]2=[O:17])(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 178441835HCID 178441835, compound

Product 1

HCID 178441860HCID 178441860, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2.1 g (7.0 mmol) of the quinazolinone prepared in Example 18 in 15 mL of dry DMF was added 1.74 g (20.0 mmol) of sodium acetate. The mixture was heated to 60° C. for 3 hours. The reaction mixture was concentrated in vacuo and the residue dissolved in 100 mL of CH2Cl2. The solution was washed with water (3×20 mL), brine (1×20 mL) and dried over MgSO4. The mixture was filtered and concentrated in vacuo. The residue was recrystallized from MeOH/H2O to give the titled compound as a colorless solid. 68% yield. 1H-NMR (CDCl3): 0.99 (t, 3H, J=7.32 Hz), 1.50 (m, 2H), 1.83 (m, 2H), 2.14 (t, 3H), 2.77 (3 line m, 2H, J=7.71 Hz), 5.23 (s, 2H), 7.69-7/78 (m, 2H), 8.25 (s, 1H), 10.90 (bs, 2H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in 100 mL of CH2Cl2
  3. washThe solution was washed with water (3×20 mL), brine (1×20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-d5cc3aa040424c8486dd4c5f6f065f65
Source dataset
uspto-grants-1993_08
Patent number
US05238942

Reaction notes

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