Dimethylformamide → HCID 178441860, compound

HRID 373118Notes

Reaction equation

HRID 373118 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[N:11]=[CH:10][NH:9][C:7](=[O:8])[C:5]=2[CH:6]=1.[C:12]([O-:15])(=O)[CH3:13].[Na+].CN([CH:20]=[O:21])C>>[C:12]([O:21][CH2:20][C:1]1[CH:6]=[C:5]2[C:4](=[CH:3][CH:2]=1)[NH:11][C:10]([CH2:2][CH2:1][CH2:6][CH3:5])=[N:9][C:7]2=[O:8])(=[O:15])[CH3:13]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 1354087534(1H)-Quinazolinone

Product 1

HCID 178441860HCID 178441860, compoundYield 68%

Conditions

Temperature
60 °C

Procedure

To a solution of 2.1 g (7.0 mmol) of the quinazolinone prepared in Example 12 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 1.31 g (4.8 mmol) of 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-ee28ce58343b4c7e93f3b3b7f6b436fe
Source dataset
uspto-grants-1992_11
Patent number
US05162325

Reaction notes

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