4-(Dimethylamino)Benzaldehyde → N,N-dimethylformamide ethanol

HRID 1190827Notes

Reaction equation

HRID 1190827 reaction equation
[CH3:1][O-:2].[Na+].[O:4]1C2C=CC=CC=2N[C:6](=O)[CH2:5]1.[CH3:15][N:16](C)[C:17]1C=C[C:20]([CH:21]=[O:22])=CC=1>CN(C=O)C>[CH2:5]([OH:4])[CH3:6].[CH3:15][N:16]([CH:1]=[O:2])[CH3:17].[CH2:21]([OH:22])[CH3:20]

Participants

6

Reactant 3

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

Product 2

HCID 702EthanolYield 30%HCID 19794673N,N-dimethylformamide ethanolYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HSB-9 and HSB-10: Sodium methoxide was added in one portion to a mixture of 2H-1,4-benzoxazin-3(4H)-one (10 mmol) and 4-dimethylamino benzaldehyde (16 mmol) in dry DMF (10 ml). The reaction mixture was refluxed overnight, then cooled to room temperature and poured into crushed ice and left overnight in the refrigerator. The precipitated solid was collected by filtration, washed with water and dried. The crude product was purified by recrystallisation from ethanol (30% yield) and DMF-ethanol (40% yield) respectively (40% yield).

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

Sources & evidence

ORD record
ord-ca8a7f4c3c5046859e045eda3245cd1c
Source dataset
uspto-grants-2014_03
Patent number
US08680094B2

Reaction notes

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