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

HRID 399693Notes

Reaction equation

HRID 399693 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 4-[N,N-bis-(3,4-dimethylphenyl) amino] benzene and 35.5 mL of DMF were placed in a three-neck flask, and while stirring while cooling in ice water, 84.4 mL of phosphorus oxychloride was dropped into the flask. Upon completion of the addition of the drops, the mixture solution was reacted for 5 hours at 95° C., then 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, and 4-[N,N-bis-(3,4-dimethylphenyl) amino] benzaldehyde was obtained. The amount obtained was 107.6 g (yield rate of 79.0%).

Workup

  1. additionUpon completion of the addition of the 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-4c6448ff8356485aae33044d18b1af47
Source dataset
uspto-grants-1998_10
Patent number
US05824443

Reaction notes

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