Water → N-octadecane 2,7-dichlorocarbazole

HRID 2307950Notes

Reaction equation

HRID 2307950 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40].O>CC(C)=O>[CH3:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23].[Cl:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Cl:15])=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 82181-BromooctadecaneHCID 11430Potassium CarbonateHCID 12070509Carbazole, 2,7-dichloro-

Product 1

HCID 131724694N-octadecane 2,7-dichlorocarbazoleYield 86%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3.00 g of compound 8 (12.7 mmol) in 50 mL of anhydrous acetone was added 3.51 g (25.4 mmol, Aldrich Co.) of K2CO3 and 8.47 g (25.4 mmol, Aldrich Co.) of 1-bromooctadecane. The solution was refluxed 24 h under argon. The mixture was poured into 100 mL of distillated water and the aqueous layer was extracted with three portions of diethyl ether. The combined organic fractions were washed with brine and dried over magnesium sulfate. The solvent was removed under vacuum. Recristallization from methanol followed by a recristallization in hexanes afforded 4.77 g of the title product as a white solid. M. P. 72-74° C. (Yield=86%).

Workup

  1. temperatureThe solution was refluxed 24 h under argon
  2. extractionthe aqueous layer was extracted with three portions of diethyl ether
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-26f35939c9f14ebab710f0cb47af61c6
Source dataset
uspto-grants-2004_12
Patent number
US06833432B2

Reaction notes

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