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

HRID 1049671Notes

Reaction equation

HRID 1049671 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]1([N:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:14]2[CH:21]=[CH:20][C:17]([CH:18]=O)=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.ClCCl>[C:7]1([N:13]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[CH2:1])=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 2

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

Product 1

HCID 10869403Benzenamine, 4-ethenyl-N,N-diphenyl-Yield 86%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

19 g (53 mmol) of methyltriphenylphosphonium bromide [1779-49-3] are suspended in dried THF under protective gas, and 6 g (53 mmol) of potassium tert-butoxide are added in portions at 0° C.; an immediate colour change to orange occurs. 14 g (51.2 mmol) of N,N-diphenyl-p-aminobenzaldehyde [4181-05-9] are added to the reaction solution at 0° C. The mixture is warmed to room temperature and stirred for a further 20 h. The solvent is stripped off in vacuo, the residue is taken up in dichloromethane, the solution is extracted with water, dried over magnesium sulfate, filtered, and the solvent is stripped off in vacuo. The yellow oil obtained is chromatographed over silica gel, giving 12 g (44 mmol) (86%) of a white solid having a purity of 99.5%.

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
  5. customThe yellow oil obtained
  6. customis chromatographed over silica gel

Sources & evidence

ORD record
ord-4e53dc5debeb45d4aa9e2ddc7f253c4b
Source dataset
uspto-grants-2016_07
Patent number
US09382253B2

Reaction notes

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