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

HRID 1628374Notes

Reaction equation

HRID 1628374 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-9f6f2090a097422382edb0eb7c12b0cf
Source dataset
uspto-grants-2014_07
Patent number
US08786181B2

Reaction notes

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