Dimethylformamide → Benzaldehyde, 4-(diphenylamino)-

HRID 1075217Notes

Reaction equation

HRID 1075217 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]>>[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

3

Reactant 2

HCID 6228DimethylformamideHCID 11775Triphenylamine

Product 1

HCID 77846Benzaldehyde, 4-(diphenylamino)-

Conditions

Temperature
90 °C

Procedure

46 g of phosphoryl trichloride (POCl3) was added dropwise to 22 g of N,N-dimethylformamide while stirring on a ice bath, and the stirring was continued for about 1 hour to produce a sirupy Vilsmeier reagent. To this reagent, a solution containing 50 g of N,N,N-triphenylamine in 200 ml of N,N-dimethylformamide was added while maintaining on the ice bath. After continued the stirring for about 1 hour, the temperature of the bath was raised to about 90° C., and the mixture was stirred for 2 additional hours. After the reaction, the mixture was cooled to room temperature and poured into ice. The resulted aqueous solution was neutralized with alkali to form a yellow precipitate. After it was separated by filtration and dried, it was recrystallized with ethyl alcohol to obtain 43 g of p-(N,N-diphenylamino)benzaldehyde.

Workup

  1. additionwas added
  2. customstirring for about 1 hour
  3. customAfter the reaction
  4. temperaturethe mixture was cooled to room temperature
  5. additionpoured into ice
  6. customto form a yellow precipitate
  7. customAfter it was separated by filtration
  8. customdried
  9. customit was recrystallized with ethyl alcohol

Sources & evidence

ORD record
ord-91926e81475f439ebebbf4046de22719
Source dataset
uspto-grants-1983_07
Patent number
US04395473

Reaction notes

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