Benzaldehyde, 4-(diphenylamino)- → Benzenamine, 4-ethenyl-N,N-diphenyl-

HRID 590900Notes

Reaction equation

HRID 590900 reaction equation
[Br-].C[PH3+].[CH3:4]C(C)([O-])C.[K+].[C:10]1([N:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]2[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1.ClCCl>[C:10]1([N:16]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[CH2:4])=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 77846Benzaldehyde, 4-(diphenylamino)-HCID 22020909HCID 22020909, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10869403Benzenamine, 4-ethenyl-N,N-diphenyl-

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

19 g of methylphosphonium bromide is suspended in dried THF under protective gas, and 6 g of potassium tert-butoxide are added in portions at 0° C. An immediate colour change to orange occurs. 14 g of N,N-diphenyl-p-aminobenzaldehyde are added to the reaction solution at 0° C. The mixture is warmed to room temperature and stirred for a further 20 hours. The solvent is stripped off in vacuo, the residue is taken up in dichloromethane, and the solution is extracted with water dried over magnesium sulfate, filtered, and the solvent is stripped off in vacuo.

Workup

  1. additionare added in portions at 0° C
  2. extractionthe solution is extracted with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9bd8aa99a9604f929763464e9696a24c
Source dataset
uspto-grants-2016_01
Patent number
US09236571B2

Reaction notes

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