4-(Dimethylamino)Benzaldehyde → HCID 69637149, compound

HRID 1825738Notes

Reaction equation

HRID 1825738 reaction equation
C[O-].[Na+].[O:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[NH:7][C:6](=[O:14])[CH2:5]1.[CH3:15][N:16]([CH3:25])[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1>CN(C=O)C>[CH3:15][N:16]([CH3:25])[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[C:5]2[C:6](=[O:14])[NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[O:4]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 74794-(Dimethylamino)BenzaldehydeHCID 727572H-1,4-benzoxazin-3(4H)-oneHCID 10942334Sodium Methoxide

Product 1

HCID 69637149HCID 69637149, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium methoxide (0.65 g, 0.012 mol) was added in one portion to a mixture of 2H-1,4-benzoxazin-3(4H)-one (1.49 g, 0.01 mol) and 4-dimethylamino benzaldehyde (2.38 g, 0.016 mol) in dry DMF (10 ml). The reaction mixture was refluxed overnight, then cooled to room temperature and poured into crushed ice. The precipitated solid was collected by filtration, washed with water and dried. The crude product was purified by recrystallization from ethanol.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. additionpoured
  3. custominto crushed ice
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried
  7. customThe crude product was purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-ccf91ed63b29478dbce2b060190a49a7
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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