Dimethylformamide → Benzaldehyde, 4-(diphenylamino)-

HRID 1608711Notes

Reaction equation

HRID 1608711 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[C:11]1([N:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([O-])(=O)C.[Na+]>O>[C:24]1([N:17]([C:11]2[CH:12]=[CH:13][C:14]([CH:8]=[O:9])=[CH:15][CH:16]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11775TriphenylamineHCID 24813Phosphorus oxychlorideHCID 517045Sodium Acetate

Product 1

HCID 77846Benzaldehyde, 4-(diphenylamino)-Yield 78.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Phosphorus oxychloride (MW 153, 0.129M, 19.7 g) was added dropwise to dimethylformamide ("DMF") (MW 73, 0.774M, 56.5 g) maintaining the temperature at <10° C. with external cooling. Triphenylamine (MW 245, 0.129M, 31.5 g) was added and the reaction mixture stirred at 100° C. for 1 hour. After cooling to room temperature and pouring into water (500 ml), the suspension was neutralised to pH 6 with saturated sodium acetate solution. The suspension was filtered off and washed with water, then redissolved in dichloromethane and dried over MgSO4 before screening through Silica gel (MERCK 60H Art 7736) and solvent removed under reduced pressure to give 27.5 g of 4-(N,N-diphenylamino) benzaldehyde (78% yield) as a yellow solid, m.p. 132°-133° C.

Workup

  1. temperaturemaintaining the temperature at <10° C. with external cooling
  2. temperatureAfter cooling to room temperature
  3. filtrationThe suspension was filtered off
  4. washwashed with water
  5. dissolutionredissolved in dichloromethane
  6. dry with materialdried over MgSO4
  7. customremoved under reduced pressure

Sources & evidence

ORD record
ord-a2d3bfb81da4428aa36f23a989458e9e
Source dataset
uspto-grants-1995_03
Patent number
US05395969

Reaction notes

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