Diethyl Ether → N-isobutyl-2,3,4,5-tetraphenylcyclopentadieneimine

HRID 890847Notes

Reaction equation

HRID 890847 reaction equation
[C:1]1([C:7]2[C:11](=O)[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:9]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:8]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:31]([NH2:35])[CH:32]([CH3:34])[CH3:33].CCOCC>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[CH2:31]([N:35]=[C:11]1[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:9]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:8]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[C:7]1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:32]([CH3:34])[CH3:33]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6558IsobutylamineHCID 680682,3,4,5-Tetraphenyl-2,4-cyclopentadien-1-one

Product 1

HCID 22247244N-isobutyl-2,3,4,5-tetraphenylcyclopentadieneimineYield 67.1%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

3 g (7.8 mmol) of tetraphenylcyclopentadienone and 3.49 ml (35.1 mmol) of isobutylamine were dissolved in 50 ml of toluene and 0.7 ml(5.85 mmol) of TiCl4 was added thereto at 0° C. The resulting mixture was agitated for 30 minutes at room temperature and then refluxed for 12 hours. The reaction mixture was cooled and ether was added thereto to induce solid precipitation. The resultant solid was filtered and dried to obtain 2.3 g of the title compound.

Workup

  1. customat 0° C
  2. temperaturerefluxed for 12 hours
  3. temperatureThe reaction mixture was cooled
  4. customsolid precipitation
  5. filtrationThe resultant solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-5578b849eecc45f59d9dea0c31091355
Source dataset
uspto-grants-2006_02
Patent number
US06998498B2

Reaction notes

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