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

HRID 378761Notes

Reaction equation

HRID 378761 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-694eee9d0e7a4157bdeed6c3d21fc6bc
Source dataset
uspto-grants-2001_10
Patent number
US06296978B1

Reaction notes

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