1-Bromo-2-Chloroethane → 3,6-bis(2-chloroethoxy)-N-ethylcarbazole

HRID 1580080Notes

Reaction equation

HRID 1580080 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:22][CH3:23])[C:10]3[C:15]([C:16]=2[CH:17]=1)=[CH:14][C:13]([O:18]C(=O)C)=[CH:12][CH:11]=3)(=O)[CH3:2].Br[CH2:25][CH2:26][Cl:27].C[O-].[Na+].[Cl:31]C1C=CC=CC=1>>[Cl:27][CH2:26][CH2:25][O:18][C:13]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:22][CH3:23])[C:8]3[C:16]([C:15]=2[CH:14]=1)=[CH:17][C:5]([O:4][CH2:1][CH2:2][Cl:31])=[CH:6][CH:7]=3

Participants

5

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 7964ChlorobenzeneHCID 10942334Sodium MethoxideHCID 12331788N-ethyl-3,6-carbazolediol diacetate

Product 1

HCID 215523293,6-bis(2-chloroethoxy)-N-ethylcarbazole

Procedure

To a stirred mixture of 31.1g (0.1 mole) of N-ethyl-3,6-carbazolediol diacetate and 39.4 g (0.3 mole) of 1-bromo-2-chloroethane in 400 ml of chlorobenzene is added 0.2 mole of sodium methoxide. Upon complete addition of the alkali, the mixture is refluxed with stirring for 18 hours, then cooled. The supernatant water layer is decanted and the residue is taken up in ethanol. The solid which separates is filtered and recrystallized from ethanol-chloroform to give 3,6-bis(2-chloroethoxy)-N-ethylcarbazole.

Workup

  1. additionUpon complete addition of the alkali
  2. temperaturethe mixture is refluxed
  3. temperaturecooled
  4. customThe supernatant water layer is decanted
  5. filtrationThe solid which separates is filtered
  6. customrecrystallized from ethanol-chloroform

Sources & evidence

ORD record
ord-7c684a13f721420c9efac940e5f57949
Source dataset
uspto-grants-1976_01
Patent number
US03932424

Reaction notes

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