Dimethylformamide → 4-[N,N-bis(3,4-dimethylphenyl)amino]benzaldehyde

HRID 2294619Notes

Reaction equation

HRID 2294619 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[C:12]([CH3:17])[CH:11]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].CN([CH:27]=[O:28])C.P(Cl)(Cl)(Cl)=O>O>[CH3:17][C:12]1[CH:11]=[C:10]([N:9]([C:18]2[CH:23]=[CH:22][C:21]([CH:27]=[O:28])=[CH:20][CH:19]=2)[C:4]2[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=2)[CH:15]=[CH:14][C:13]=1[CH3:16]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 21696495N-(3,4-Dimethylphenyl)-3,4-dimethyl-N-phenylaniline

Product 1

HCID 226170914-[N,N-bis(3,4-dimethylphenyl)amino]benzaldehyde

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

124.6 g of [N,N-bis-(3,4-dimethylphenyl)amino]benzene and 35.5 mL of DMF were placed in a three-neck flask. While stirring and cooling in ice water, 84.4 mL of phosphorus oxychloride was dropped into the flask. Upon completion of addition of drops, the mixture solution was reacted for 5 hours at 95° C., poured into 4 L of warm water, and stirred for 1 hour. The precipitate was collected and washed in a :1:1 mixture solution of ethanol/water. 4-[N,N-bis-(3,4-dimethylphenyl)amino]benzaldehyde was obtained. The yield was 107.6 g (yield rate of 79.0%).

Workup

  1. additionUpon completion of addition of drops
  2. customthe mixture solution was reacted for 5 hours at 95° C.
  3. stirringstirred for 1 hour
  4. customThe precipitate was collected
  5. washwashed in a :1:1 mixture solution of ethanol/water

Sources & evidence

ORD record
ord-46895a419216472bbc897fcbccdb52a2
Source dataset
uspto-grants-1997_11
Patent number
US05688961

Reaction notes

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