Dimethylformamide → Benzaldehyde, 4-(diphenylamino)-

HRID 2294622Notes

Reaction equation

HRID 2294622 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([CH:23]=[O:24])C.P(Cl)(Cl)(Cl)=O>O>[C:14]1([N:7]([C:1]2[CH:2]=[CH:3][C:4]([CH:23]=[O:24])=[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)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

101.4 g of triphenylamine 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. The temperature was increased to 95° C. and the mixture was reacted for 5 hours. 4 L of warm water was poured into the flask and the mixture was stirred for one hour. A precipitate was collected and washed in a 1:1 mixture solution of ethanol/water. 4-(N,N-diphenylamino)benzaldehyde was obtained. The yield was 91.5 g (yield rate of 81.0%), and the melting point was 128.6°-130.1° C.

Workup

  1. customthe mixture was reacted for 5 hours
  2. stirringthe mixture was stirred for one hour
  3. customA precipitate was collected
  4. washwashed in a 1:1 mixture solution of ethanol/water

Sources & evidence

ORD record
ord-1aa14b6ed1c2489fbf181ac33d9c877e
Source dataset
uspto-grants-1997_11
Patent number
US05688961

Reaction notes

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