Water → 9-(2-Chloroethyl)carbazole

HRID 1860349Notes

Reaction equation

HRID 1860349 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:14][CH2:15][CH2:16]OS(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+].O>CC(C)=O>[Cl:14][CH2:15][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

Participants

6

Reactant 4

HCID 962WaterHCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 6854CarbazoleHCID 14798Sodium Hydroxide

Product 1

HCID 143539-(2-Chloroethyl)carbazoleYield 43.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

17.9 g (107 mmol) of carbazole and 500 ml of acetone as solvent were placed in a 1000 ml four-necked flask with a mechanical stirrer and bulb-shaped cooler. To this was added an aqueous solution prepared from 22.0 g (93.7 mmol)of 2-chloroethyl-p-toluene sulfonate, 12.5 g of sodium hydroxide and 9.2 ml of water. The resultant product was heated to 60° C. in a silicone oil bath, and subjected to the reaction for 20 hours. After the reaction was completed, the product was cooled to the ambient temperature. The precipitated solid was subjected to suction filtration with a glass filter. The resultant liquid was concentrated in an evaporator and dried under vacuum to obtain a brown solid, which was recrystallized in the presence of ligroin to obtain 9.3 g of a white crystal.

Workup

  1. additionTo this was added an aqueous solution
  2. customsubjected to the reaction for 20 hours
  3. filtrationThe precipitated solid was subjected to suction filtration with a glass
  4. filtrationfilter
  5. concentrationThe resultant liquid was concentrated in an evaporator
  6. customdried under vacuum
  7. customto obtain a brown solid, which
  8. customwas recrystallized in the presence of ligroin

Sources & evidence

ORD record
ord-443f5ab4f0a64558aabceff952a781e8
Source dataset
uspto-grants-2003_03
Patent number
US06528657B2

Reaction notes

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