Chloroethane → N-ethyl carbazole

HRID 1656667Notes

Reaction equation

HRID 1656667 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.Cl[C:15]1C=CC=C[C:16]=1Cl.C(Cl)C.[OH-].[Na+]>C(N(CC)CC)C>[CH2:15]([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)[CH3:16]

Participants

6

Reactant 4

HCID 6337ChloroethaneHCID 6854CarbazoleHCID 72391,2-DichlorobenzeneHCID 14798Sodium Hydroxide

Product 1

HCID 6836N-ethyl carbazole

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

A 0.5-liter autoclave equipped with a stirrer was charged with carbazole (82.0 g), o-dichlorobenzene (100 g), ethyl chloride (40.2 g), 48% sodium hydroxide (73.9 g) and triethylamine (5 g). After the atmosphere in the autoclave was replaced with nitrogen gas, the autoclave was heated to the reaction temperature of 100° C. and the reaction mixture was stirred at the same temperature for 9 hours, while keeping the temperature. After completion of the reaction, the mixture was cooled to 50° C., and was transferred into a separatory funnel. The autoclave was washed with o-dichlorobenzene and water. The washings were combined with the reaction mass, and the combined mixture was separated. The separated organic layer was washed with a 25% sulfuric acid solution to neutralize base traces, and the water layer was removed by separation to give 273.0 g of an o-dichlorobenzene solution of N-ethylcarbazole. The analysis of this solution by chromatography revealed that the content of N-ethylcarbazole was 34.9% and the yield thereof was 99.6%.

Workup

  1. customA 0.5-liter autoclave equipped with a stirrer
  2. customAfter completion of the reaction
  3. temperaturethe mixture was cooled to 50° C.
  4. customwas transferred into a separatory funnel
  5. washThe autoclave was washed with o-dichlorobenzene and water
  6. customthe combined mixture was separated
  7. washThe separated organic layer was washed with a 25% sulfuric acid solution
  8. customthe water layer was removed by separation

Sources & evidence

ORD record
ord-c9fa3692eb2e4098846305f7f38fcae5
Source dataset
uspto-grants-1993_10
Patent number
US05254700

Reaction notes

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