Chloroethane → N-ethyl carbazole

HRID 1656668Notes

Reaction equation

HRID 1656668 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.[CH2:14](Cl)[CH3:15].[OH-].[Na+].C(N(CCCC)CCCC)CCC>ClC1C=CC=CC=1Cl>[CH2:14]([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)[CH3:15]

Participants

6

Reactant 4

HCID 6337ChloroethaneHCID 6854CarbazoleHCID 7622TributylamineHCID 14798Sodium Hydroxide

Product 1

HCID 6836N-ethyl carbazole

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent2×

Conditions

Temperature
100 °C

Procedure

A 0.5-liter autoclave equipped with a stirrer was charged with carbazole (82.4 g), o-dichlorobenzene (100 g), ethyl chloride (40.2 g), 48% sodium hydroxide (55.8 g) and tributylamine (9.2 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. The same procedures as those described in Example 1 gave 275.9 g of an o-dichlorobenzene solution of N-ethylcarbazole. The analysis of this solution by chromatography revealed that the content of N-ethylcarbazole was 32.9% and the yield thereof was 94.3%.

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

Sources & evidence

ORD record
ord-e4dbaa8cfaeb4d478eeaa4415b3a3677
Source dataset
uspto-grants-1993_10
Patent number
US05254700

Reaction notes

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