1,4-Dichlorobenzene → N~1~,N~1~,N~4~,N~4~-Tetrabutylbenzene-1,4-diamine

HRID 276156Notes

Reaction equation

HRID 276156 reaction equation
[CH:1]1[C:6](Cl)=[CH:5][CH:4]=[C:3](Cl)[CH:2]=1.[CH2:9]([NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12].C[C:19]([O-])([CH3:21])[CH3:20].[K+].[Br-].[Li+]>C1(C)C=CC=CC=1>[CH2:9]([N:13]([C:6]1[CH:5]=[CH:4][C:3]([N:13]([CH2:14][CH2:20][CH2:19][CH3:21])[CH2:9][CH2:10][CH2:11][CH3:12])=[CH:2][CH:1]=1)[CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 46851,4-DichlorobenzeneHCID 8148DibutylamineHCID 82050Lithium BromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 351067N~1~,N~1~,N~4~,N~4~-Tetrabutylbenzene-1,4-diamineYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

30 mmol of p-dichlorobenzene (4.4 g), 70 mmol of di-n-butylamine (9.0 g), 70 mmol of KOtBu (7.9 g), 30 mmol of lithium bromide (2.6 g) and 44 mg of trans-di-μ-acetatobis[2-[bis(1,1-dimethylethyl)phosphino]μ-2-methylpropyl-C,P]dipalladium(II) (0.2 mol %) are suspended in 75 ml of toluene and placed in a pressure tube under protective gas. After 12 hours at 140° C., an aqueous work-up is carried out. After the aqueous phase has been extracted twice with toluene, the combined organic phases are dried over magnesium sulfate and freed of the solvents on a rotary evaporator. Distillation gives 1,4-bis(N,N-dibutylamino)benzene as a virtually colorless liquid having a boiling point of 143° C./10 torr; yield: 77%.

Workup

  1. customplaced in a pressure tube under protective gas
  2. extractionAfter the aqueous phase has been extracted twice with toluene
  3. dry with materialthe combined organic phases are dried over magnesium sulfate
  4. customfreed of the solvents on a rotary evaporator
  5. distillationDistillation

Sources & evidence

ORD record
ord-79547a514787425abb1b9bc73b2f9cd1
Source dataset
uspto-grants-2002_03
Patent number
US06353136B1

Reaction notes

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