2,4-Dimethylaniline → HCID 22247510, compound

HRID 889799Notes

Reaction equation

HRID 889799 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=1[CH3:30])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2Br)=[CH:12][CH:11]=1.[CH3:31][C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[CH:34][C:33]=1[NH2:39].C(O[Na])(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([C:23]1[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][C:24]=1[CH3:30])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([NH:39][C:33]3[CH:34]=[CH:35][C:36]([CH3:38])=[CH:37][C:32]=3[CH3:31])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1

Participants

7

Reactant 3

HCID 72502,4-DimethylanilineHCID 22247506HCID 22247506, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 22247510HCID 22247510, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 7237O-XyleneSolvent

Procedure

Into a 1 liter three-necked reaction vessel fitted with a cooling tube and a mechanical stirrer, 91.3 g (0.2 mol) of bis(2,4-dimethylphenyl)[4-(bromophenyl)phenyl]amine, 36.3 g (0.3 mol) of 2,4-dimethylphenylamine, 2.24 g (0.01 mol) of palladium acetate, 11.1 g (0.02 mol) of bis(diphenylphosphino)ferrocene, 26.9 g (0.28 mol) of tert-butoxysodium and 500 mL of xylene were introduced to effect reflux for 3 hours in a nitrogen gas atmosphere and with heating in an oil bath. After the reaction was completed, the reaction mixture was left to cool to room temperature, followed by extraction with toluene/water, then washing with hydrochloric acid water, and thereafter distillation of the organic layer under reduced pressure and purification with a silica gel column (developer solvent: hexane/toluene=1:1) to give the desired bis(2,4-dimethylphenyl)(4-{4-[(2,4-dimethylphenyl)amino]phenyl}phenyl)amine. The compound obtained was in a yield of 83.4 g corresponding to 84%. The compound obtained was measured with the same elementary analyzer as the above.

Workup

  1. customInto a 1 liter three-necked reaction vessel fitted with a cooling tube and a mechanical stirrer
  2. temperaturereflux for 3 hours in a nitrogen gas atmosphere
  3. temperaturewith heating in an oil bath
  4. waitthe reaction mixture was left
  5. extractionfollowed by extraction with toluene/water
  6. washwashing with hydrochloric acid water
  7. distillationdistillation of the organic layer
  8. customunder reduced pressure and purification with a silica gel column (developer solvent: hexane/toluene=1:1)

Sources & evidence

ORD record
ord-2fe716f7b0bc46b494ea00367cc9f67d
Source dataset
uspto-grants-2006_02
Patent number
US06994941B2

Reaction notes

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