Carbazole → 9-Tetradecyl-9H-carbazole

HRID 983374Notes

Reaction equation

HRID 983374 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.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[OH-].[Na+].C(N1C2C=CC=CC=2C2C1=CC=CC=2)CCCCCC>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1>[CH2:28]([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)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15]

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 8208Myristyl bromideHCID 14798Sodium HydroxideHCID 138604829-Heptyl-9H-carbazole

Product 1

HCID 123386279-Tetradecyl-9H-carbazole

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 1140TolueneSolvent

Procedure

N-Tetradecylcarbazole was prepared from carbazole (59.27 g, 0.35 mol), 1-bromotetradecane (100 g, 0.36 mol, commercially available from Aldrich, Milwaukee, Wis.), benzyltriethyl ammonium chloride (4.00 g, 0.018 mol), 50% aqueous NaOH (200 g), and toluene (400 ml) according to the procedure described for N-heptylcarbazole. The product was obtained as 120 g of a brown liquid (93% yield). Upon standing at room temperature overnight, the liquid solidified.

Sources & evidence

ORD record
ord-2cda71b26e444dbcaf1db25ceb075213
Source dataset
uspto-grants-2005_03
Patent number
US06864025B2

Reaction notes

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