Carbazole → N-2-Ethylhexylcarbazole

HRID 983376Notes

Reaction equation

HRID 983376 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.C([CH:16]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:17]Br)C.[OH-].[Na+].[CH2:25](N1C2C=CC=CC=2C2C1=CC=CC=2)[CH2:26]CCCCC>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH3:25][CH2:26][N:12]1[C:11]2[C:10]([CH2:17][CH2:16][CH2:19][CH2:20][CH2:21][CH3:22])=[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

7

Reactant 4

HCID 6854CarbazoleHCID 14798Sodium HydroxideHCID 868042-Ethylhexyl bromideHCID 138604829-Heptyl-9H-carbazole

Product 1

HCID 66872719N-2-Ethylhexylcarbazole

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

N-2-Ethylhexylcarbazole was prepared from carbazole (85.09 g, 0.51 mol), 2-ethylhexylbromide (100 g, 0.52 mol, commercially available from Aldrich, Milwaukee, Wis.), benzyltriethyl ammonium chloride (5.78 g, 0.025 mol), toluene (400 ml), and 50% aqueous NaOH solution (200 g) according to the procedure described for N-heptylcarbazole. The product was obtained as 115 g of brownish liquid (81% yield).

Sources & evidence

ORD record
ord-9fbf4fceb2d94378bc29d0bf9621c2d9
Source dataset
uspto-grants-2005_03
Patent number
US06864025B2

Reaction notes

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