Dimethylformamide → Benzaldehyde, 4-(diphenylamino)-

HRID 2294618Notes

Reaction equation

HRID 2294618 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)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

101.4 g of triphenylamine and 35.5 mL of dimethyl formamide (DMF) were placed in a three-neck flask, and while stirring and cooling in ice water, 84.4 mL of phosphorus oxychloride was dropped into the flask. The temperature was raised to 95° C. The mixture was reacted for 5 hours. The reaction solution was poured into 4 L of warm water and stirred for one hour. The 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%). The melting point was 128.6°-130.1° C.

Workup

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

Sources & evidence

ORD record
ord-3010cebef39643bfb211898922e1d99f
Source dataset
uspto-grants-1997_11
Patent number
US05688961

Reaction notes

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