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Aniline → Bis-(6-bromo-hexyl)-phenyl-amine

HRID 494902
Notes
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Reaction equation

HRID 494902 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:9]([Br:15])[CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[C:16]([O-])(=O)[CH3:17].[Na+]>O>[Br:15][CH2:9][CH2:10][CH2:11][CH2:12][CH2:16][CH2:17][N:1]([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][Br:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6115AnilineHCID 517045Sodium AcetateHCID 118068541,1-Dibromohexane

Product 1

HCID 67270812Bis-(6-bromo-hexyl)-phenyl-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
97.5 °C

Procedure

0.45 ml of aniline (5 mmol), 2.5 ml of dibromohexane (14.6 mmol), and sodium acetate (14.5. mmol) were charged in a reaction container and slowly heated to about 95 to 100° C. while generating bubbles under a nitrogen atmosphere. The reactant mixture was agitated for about 10 hours at about 95 to 100° C. The mixture was cooled down to room temperature, mixed with 30 ml of distilled water, and agitated for 10 minutes. The mixture was then treated to extract organic layers using ethylacetate, and then was distillated through reduced pressure distillation, thereby obtaining a sticky liquid. The sticky liquid was separated using preparative TLC (eluent: CH2Cl2:Hexane=1:2.5). The obtained compound was confirmed to be the compounds 221 of FIG. 3 using a 1H-NMR spectometry and mass spectometry. The results are shown in FIG. 5.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. stirringagitated for 10 minutes
  3. additionThe mixture was then treated
  4. extractionto extract organic layers
  5. distillationwas distillated through reduced pressure distillation
  6. customobtaining a sticky liquid
  7. customThe sticky liquid was separated

Sources & evidence

ORD record
ord-c35e959f12a949f7b352ec623a24a14b
Source dataset
uspto-grants-2009_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07538199B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes