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

HRID 1419666Notes

Reaction equation

HRID 1419666 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]benzaldehydeYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

Into a three-necked flask, 124.6 g of [N,N-bis(3,4-dimethylphenyl)amino]benzene and 35.5 ml of DMF were placed, and 84.4 ml of phosphorus oxychloride was added dropwise thereto with stirring while cooling with ice water. After the addition was completed, the mixture solution was heated to 95° C. to carry out reaction for 5 hours. The reaction solution obtained was poured into 4 liters of warm water, followed by stirring for 1 hour. Thereafter, the precipitate was collected by filtration, and washed with a mixture of ethanol/water (1:1) to obtain 4-[N,N-bis(3,4-dimethylphenyl)amino]benzaldehyde in an amount of 107.6 g (yield: 79.0%).

Workup

  1. additionAfter the addition
  2. customreaction for 5 hours
  3. customThe reaction solution obtained
  4. stirringby stirring for 1 hour
  5. filtrationThereafter, the precipitate was collected by filtration
  6. washwashed with a mixture of ethanol/water (1:1)

Sources & evidence

ORD record
ord-0a28548b2f0748f19fac11e0e31858f4
Source dataset
uspto-grants-1999_03
Patent number
US05888690

Reaction notes

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