Dimethylformamide → Benzaldehyde, 4-(diphenylamino)-

HRID 378759Notes

Reaction equation

HRID 378759 reaction equation
[C:1]1([N:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)[CH:22]=[O:23].P(Cl)(Cl)(Cl)=O>O>[C:14]1([N:7]([C:1]2[CH:2]=[CH:3][C:4]([CH:22]=[O:23])=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11775TriphenylamineHCID 24813Phosphorus oxychloride

Product 1

HCID 77846Benzaldehyde, 4-(diphenylamino)-Yield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

Into a three-necked flask, 101.4 g of triphenylamine and 35.5 ml of DMF (dimethylformamide) were placed, and 84.4 ml of phosphorus oxychloride was added dropwise thereto with stirring while cooling with ice water, and then the temperature was raised 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 formed was collected by filtration, and washed with a mixture of ethanol/water (1:1) to obtain 4-(N,N-diphenylamino)benzaldehyde in an amount of 91.5 g (yield: 81.0%).

Workup

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

Sources & evidence

ORD record
ord-17534e2ccb6c45a8bd9e00cfe1233de6
Source dataset
uspto-grants-2001_10
Patent number
US06296978B1

Reaction notes

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