Water → N-tosyl-3-iodocarbazole

HRID 1514009Notes

Reaction equation

HRID 1514009 reaction equation
[S:1](Cl)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[I:12][C:13]1[CH:14]=[CH:15][C:16]2[NH:17][C:18]3[C:23]([C:24]=2[CH:25]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3.[OH-].[K+].O>CC(C)=O.C(Cl)Cl.CCO>[I:12][C:13]1[CH:14]=[CH:15][C:16]2[N:17]([S:1]([C:4]3[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=3)(=[O:3])=[O:2])[C:18]3[C:23]([C:24]=2[CH:25]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3

Participants

7

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 36780693-iodo-9H-carbazole

Product 1

HCID 66974690N-tosyl-3-iodocarbazoleYield 61.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

Tosyl chloride (8.4 g, 44 mmol) was added to a solution of 3-iodocarbazole (11.7 g, 40 mmol) and grounded KOH (2.7 g, 48 mmol) in 200 mL of acetone. The mixture was refluxed for 3 hours, and then cooled down. It was poured into 1 L of cold water while stirring. After sitting for 30 minutes, the liquid was decanted. The crude product was thus obtained as sticky solid on the beaker wall. About 11 g of pure 3-iodo-9-tosylcarbazole was obtained after recystallization from CH2Cl2/EtOH.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. temperaturecooled down
  3. customthe liquid was decanted
  4. customThe crude product was thus obtained as sticky solid on the beaker wall

Sources & evidence

ORD record
ord-01b720d622384240bf43cdfd9457dc92
Source dataset
uspto-grants-2012_07
Patent number
US08221905B2

Reaction notes

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