Carbazole → N-Benzylcarbazole

HRID 1597734Notes

Reaction equation

HRID 1597734 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.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:22]([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)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 14797Potassium Hydroxide

Product 1

HCID 146485N-BenzylcarbazoleYield 87.3%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

20 g (119.6 mmol) of carbazole, 47 g (712.0 mmol) of 85% KOH, 26.5 g (191.7 mmol) of potassium carbonate, 4.0 g (11.8 mmol) of tetra-n-butylammonium hydrogensulfate, 17.0 g (134.3 mmol) of benzyl chloride and 300 ml of toluene were allowed to react and after treated in the same manner as with Example 7 (1) to obtain 26.88 g of 9-benzylcarbazole.

Workup

  1. customto react

Sources & evidence

ORD record
ord-aab5f63b8df348529708c5acc16debe0
Source dataset
uspto-grants-1998_04
Patent number
US05736284

Reaction notes

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