Carbazole → N-Butylcarbazole

HRID 1734749Notes

Reaction equation

HRID 1734749 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[CH2:16](Br)[CH2:17][CH2:18][CH3:19]>C1(C)C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[CH2:16]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 3

HCID 6854Carbazole2×HCID 8002Butyl bromideHCID 14797Potassium Hydroxide

Product 1

HCID 73872N-Butylcarbazole

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A suspension of 100 g (0.6 mol) of carbazole in 200 ml of toluene is heated under reflux, with stirring. After cooling to 95°, first 26.8 g (0.12 mol) of triethylbenzylammonium chloride and then a solution of 169.8 g of KOH in 180 ml of water are added. The temperature thereby drops to 65°. 205.6 g (1.5 mol) of butyl bromide are now added in the course of 5 minutes, with vigorous stirring, whereupon the temperature rises to 92°. The mixture is kept under reflux for a further 10 minutes, all the carbazole dissolving. The aqueous phase is then removed. The toluene phase is washed with a little water, dried over Na2CO3 and evaporated in vacuo. The oily residue is dissolved in 300 ml of warm hexane and the solution is clarified. On cooling, the product crystallizes in beige-coloured crystals of melting point 50°-52°.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperatureAfter cooling to 95°
  4. customthereby drops to 65°
  5. customrises to 92°
  6. temperatureunder reflux for a further 10 minutes
  7. customThe aqueous phase is then removed
  8. washThe toluene phase is washed with a little water
  9. dry with materialdried over Na2CO3
  10. customevaporated in vacuo
  11. dissolutionThe oily residue is dissolved in 300 ml of warm hexane
  12. temperatureOn cooling
  13. customthe product crystallizes in beige-coloured crystals of melting point 50°-52°

Sources & evidence

ORD record
ord-449c47f17d194fb9858ca5bb5f399b77
Source dataset
uspto-grants-1996_07
Patent number
US05534629

Reaction notes

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