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

HRID 1755500Notes

Reaction equation

HRID 1755500 reaction equation
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[C:28]1([N:34]([C:41]2[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O1CCCC1>[C:28]1([N:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:41]2[CH:48]=[CH:47][C:44]([CH:45]=[CH2:2])=[CH:43][CH:42]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 77846Benzaldehyde, 4-(diphenylamino)-HCID 638159Methyltriphenylphosphonium iodideHCID 23665647Potassium tert-butoxide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

In a two necked flask, under argon atmosphere, 22.18 g (54.87 mmol) of methyl(triphenyl)phosphonium iodide are dissolved in 100 mL of freshly distilled tetrahydrofuran (THF). After the mixture is cooled to the temperature of 0° C., 1.5 eq. (6.16 g) of potassium tert-butoxide are incorporated. After 30 min of stirring at 0° C., a solution of 4-(N,N-diphenylamino)-benzaldehyde (10 g, 36.80 mmol) in 30 mL of THF is added to the mixture, drop by drop. The temperature of the medium is then left to return to ambient temperature and the stirring continued for 4 additional hours. The medium is then hydrolysed with a saturated sodium carbonate solution then extracted in dichloromethane. The organic phase is washed successively with water, a saturated NaCl solution then dried on Na2SO4. After filtration and evaporation, the crude product is purified on chromatography column on silica [eluent—hexane/ethyl ether: 80/20].

Workup

  1. waitThe temperature of the medium is then left
  2. customto return to ambient temperature
  3. extractionhydrolysed with a saturated sodium carbonate solution then extracted in dichloromethane
  4. washThe organic phase is washed successively with water
  5. dry with materiala saturated NaCl solution then dried on Na2SO4
  6. filtrationAfter filtration and evaporation
  7. customthe crude product is purified on chromatography column on silica [eluent—hexane/ethyl ether: 80/20]

Sources & evidence

ORD record
ord-d3627ee874b34f9491a5ae59ba5aa9fe
Source dataset
uspto-grants-2015_10
Patent number
US09171676B2

Reaction notes

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