Dimethylformamide → 4-(Dibutylamino)benzaldehyde

HRID 476808Notes

Reaction equation

HRID 476808 reaction equation
[CH2:1]([N:5]([CH2:12][CH2:13][CH2:14][CH3:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].CN(C)[CH:18]=[O:19]>>[CH2:1]([N:5]([CH2:12][CH2:13][CH2:14][CH3:15])[C:6]1[CH:11]=[CH:10][C:9]([CH:18]=[O:19])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 61154N,N-Dibutylaniline

Product 1

HCID 6053914-(Dibutylamino)benzaldehyde

Conditions

Temperature
90 °C

Procedure

A 20 ml sample of N,N-dimethylformamide (DMF) was cooled to 0° C. for 1 hour and at 25° C. for 1 hour, then N,N-dibutylaniline was added slowly. The reaction mixture was heated at 90° C. for 16 hours, then cooled and poured onto 50 g of ice. A brown oil separated which was taken up in dichloromethane. The extract was washed with saturated aqueous bicarbonate then with water containing a little ammonium chloride, dried (MgSO4), and the solvent was removed at reduced pressure. The brown, oily residue was distilled in vacuo to product 6.65 g (58%) of a yellow liquid.

Workup

  1. temperaturecooled
  2. customA brown oil separated which
  3. washThe extract was washed with saturated aqueous bicarbonate
  4. dry with materialwith water containing a little ammonium chloride, dried (MgSO4)
  5. customthe solvent was removed at reduced pressure
  6. distillationThe brown, oily residue was distilled in vacuo to product 6.65 g (58%) of a yellow liquid

Sources & evidence

ORD record
ord-47a5a9b8de6f4bb1842a78ceaeee3fa6
Source dataset
uspto-grants-1989_12
Patent number
US04886339

Reaction notes

Loading…