Dimethylformamide → Benzaldehyde, 4-(diphenylamino)-

HRID 1995182Notes

Reaction equation

HRID 1995182 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]1([N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CN(C)[CH:27]=[O:28]>>[C:19]1([N:12]([C:6]2[CH:7]=[CH:8][C:9]([CH:27]=[O:28])=[CH:10][CH:11]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 11775TriphenylamineHCID 24813Phosphorus oxychloride

Product 1

HCID 77846Benzaldehyde, 4-(diphenylamino)-

Conditions

Temperature
90 °C

Procedure

A Vilsmeier's reagent was prepared by adding dropwise phosphoryl trichloride (POCl3) (46 g) to N,N-dimethylformamide (22 g) with stirring in an ice bath. Thereto there was added a solution (200 ml) of N,N,N-triphenylamine (50 g) in N,N-dimethylformamide while continuing cooling in the ice bath. The stirring was continued for about one hour, and then the bath temperature was raised to about 90° C. While maintaining that temperature, the stirring was continued further for two hours. At the conclusion of the reaction the reaction system was cooled to room temperature, and then the reaction product was poured into ice water. The thus obtained aqueous solution was neutralized with an alkali to separate out a yellow precipitate. The precipitate was filtered off, dried and then recrystallized from ethyl alcohol. Thus, p-(N,N-diphenylamino)benzaldehyde (43 g) was obtained.

Workup

  1. temperatureWhile maintaining that temperature
  2. waitthe stirring was continued further for two hours
  3. customAt the conclusion of the reaction the reaction system
  4. temperaturewas cooled to room temperature
  5. customto separate out a yellow precipitate
  6. filtrationThe precipitate was filtered off
  7. customdried
  8. customrecrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-393f0fdbb0464b9595121b88a8dd2db3
Source dataset
uspto-grants-1983_09
Patent number
US04403025

Reaction notes

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